Turning Mail.app Into the Best Mac Email App

In 2012, the Mac community lost one of the Mac OS X mail clients that many considered to be the best on the market: Sparrow. Development has stopped (which doesn’t mean you can’t still use this app, though, at least for now) since the team has been acquired by Google.

Some claim that the whole email concept needs a refresh and solutions are offered, and the previously reviewed Mail Pilot and its upcoming Mac client, or the upcoming .Mail app are proof of that. Others still prefer to use web-based apps like the popular Gmail.

I, for one, still think that Mail.app, since its OS X Lion revision, is the best. It’s built-in, offered at no cost, and is completely integrated with OS X. I’ve customized it to fit my needs and developed my own workflow to deal with emails.

In my humble opinion, you should be able to jump into your emails, process them quickly, and then get back to work. A mail client, for me, is just a way to send and receive emails, not a big messy, clunky, filing cabinet with hundreds of manually created and sorted folders. Read on to find out why, in that case, Mail.app is the best for me, even when processing hundreds of incoming messages per day.

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Smart Mailboxes and colored flags

Ever heard about the ‘Inbox Zero’? Ever struggled to achieve it?

I achieve Inbox Zero several times a day. It all depends of what you call your ‘inbox’ and how you deal with it.

I’ve set a simple Smart Mailbox that shows unread emails only. This is what I call my inbox. From now on, unless otherwise explicitely specified, when writing “my inbox”, I will refer to this smart, unread, inbox.

To add a new Smart Mailbox, just select the Mailbox > “New Smart Mailbox…” menu command within Mail.app, and define your conditions in the popup window. This is really similar to how you define a Smart Playlist in iTunes.

Setting up my inbox and using it has a double advantage:

  • once I’ve read all emails in my inbox, this inbox is truly empty,
  • which forces me to act on every incoming email as soon as I read it, otherwise it will vanish into what your software calls ‘Inbox’ and that I prefer to name “my email archive”.
Screenshot showing the Unread Smart Mailbox conditions

Setting up an ‘Unread’ Smart Mailbox is easy. Notice that, in that case, choosing ‘Any’ instead of ‘All’ in the ‘Contains messages that match’ dropdown list has the same effect, because there is only one condition.

I have a couple of other Smart Mailboxes set up:

  • “Need reply”
  • “Follow up”
  • Today
  • Sent
  • VIP
  • Trash
  • “Not flagged”

For your inspiration, there are also some other Smart Inboxes ideas across the web.

One of the key concepts of my workflow for dealing with hundreds of emails a day is:

When I read an email, I immediately decide about what to do with it.

See below for how I take my decisions.

Don’t be afraid to delete

If a message doesn’t really interest me, neither now nor in the future, I delete it immediately after reading or just “scanning” its content. No regrets.

Reply ASAP

If I need to reply to an email and can do it in a few minutes, I do it right after reading it.

The “Need Reply” Smart Mailbox

If the message needs a longer response, or more information to get or produce before replying to it, I add a blue flag to it. I have set my own keyboard shortcut for this (Option-Cmd-B, B as in ‘blue’), I will explain later how to do it. This instantly both gets it out of my inbox (because it was read) and puts it in my “Need Reply” Smart Mailbox (that has just one condition: message has a blue flag”).

When I’ve taken time to reply, I either unflag the message (Option-Cmd-B again) if I want to keep it (it will then vanish from my “Need Reply” Smart Mailbox but will be kept in my email archive), or I simply delete it.

The “Follow-up” Smart Mailbox

If the message contains information I think I might need in the following hours/days/weeks, I mark it with a green flag (with my own Option-Cmd-V shortcut, V being for “vert” which stands for green in French). All emails with a green flag go to my “Follow-up” Smart Mailbox.

When I feel I don’t need to quickly retrieve the info anymore, I simply unflag the message (with Option-Cmd-V again). Doing so, the message is not in my “Follow-up” Smart Mailbox anymore, but still in my email archive. This way I can retrieve it with a quick search in case I really need it later.

Other Smart Mailboxes

The Today, VIP, Sent, Trash, and “Not flagged” Smart Mailboxes are pretty self-explanatory. I created them just to add them to the Favorites bar and thus have a keyboard access to it. That’s useful because I choose to hide Mail’s side bar to get a cleaner UI (more on this later).

How-to: Create your own keyboard shortcuts

To flag/unflag a message as blue, I’ve set my own keyboard shortcut: Option-Cmd-B. To do this:

  1. Go into the Keyboard preference pane of OS X, choose the Keyboard Shortcuts tab, and select Application Shortcuts at the end of the list on the left.
  2. Click on the plus button on the right, and in the dropdown window that appears, choose Mail from the Application dropdown menu.
  3. In the text field next to “Menu Title:”, enter the exact name of the command you want to add, for instance Blue if it is the name of the color in the Message > Flag menu command you want to map the shortcut to.
  4. Click in the white field next to “Keyboard Shortcut” and press the key combo you want to assign, here Option-Cmd-B.
  5. Finally, click the Add button and close the Keyboard preference pane, and you’re done.
Screenshot showing how to add a new keyboard shortcut to an existing menu command in Mail.app

Setting a new keyboard shortcut for an existing menu command is relatively easy, once you know where you can do this, that is in the Keyboard preference pane of OS X.

The final trick: my previous “Need Action” Smart Mailbox and my new approach

If you carefully read the previous paragraphs, you probably noticed that I describe how to deal with messages that:

  • I’m simply not interested in
  • I need to reply, now or later
  • I want to keep at hand for a given period of time.

But what do I do if the content of the email asks me to do something?

Previously, I had another Smart Mailbox, “Need Action”. I added a red flag (with my own Option-Cmd-R shortcut) to messages asking me to do something. The “Need Action” Smart Mailbox was set to show messages with a red flag.

Over time, I felt that:

  1. adding a red flag to messages
  2. then review the “Need Action” Smart Mailbox
  3. to finally add the actions needed to my to-do list in TaskPaper

was requiring 3 steps, the two first being, in fact, unnecessary. Why not directly adding things to do to TaskPaper?

Fortunately, I found a script for TaskPaper that does exactly what I want: when you run it, “it will make a new entry in the Inbox of Taskpaper with the subject of the email and a URL that points to the email” as its creator explains it.

I even added my own Shift-Cmd-T keyboard shortcut to this script (which is actually run as a Service). So now, when I read an email that requires me to do something, I just press Shift-Cmd-T and it is added to my TaskPaper Inbox.

There is also a variation of this script that also adds a note to your new TaskPaper entry.

With all these considerations in mind, my take home message is:

There is a time for checking for new emails and decide what to do with each new one. There is another time to review your Smart Mailboxes and act on their contained emails.

These are two separate activities and you can do each of it whenever you want/can/need it to.

Just don’t re-read an email several times without doing anything: decide immediately, act on it whenever you can, and you’re done.

UI customization

When I use Mail.app, I get a really fresh and uncluttered UI by doing several modifications to the default UI, all without any third party apps.

Fully using your screen width

I use the new Mail layout, introduced in OS X 10.6 Lion, that takes advantage of the width of recent 16:9 and 16:10 monitors (uncheck “Use classic layout” in the View tab in the Mail Preferences window to achieve this).

I even expand the message list width to make it occupy approximately one fourth to one third of the window.

Showing the ‘Favorites’ bar

To get access to my favorite items from the Message Box list while keeping this list hidden, I add my smart inboxes to the Favorites bar. You can do this by simply dragging and dropping them from the Message Box list.

To make sure the Favorites bar is visible, use Shift-Option-Cmd-H or the View > “Show Favorites Bar” menu command.

To access Favorites from the Favorites bar using my keyboard, I have to press Shift+Cmd+[number]. That’s because I have a French keyboard: we need to press Shift to type a number. On an English/US keyboard, it is simply Cmd+[number].

Screenshot showing my Favorites bar

If your Favorites bar in Mail.app looks like this, pressing Cmd-Shift-1 opens “Inbox”, Cmd-Shift-2 opens “Unread”, Cmd-Shift-5 opens “Follow”, and so on.

Beware! Cmd-Shift–3 and Cmd-Shift–4 are assignated by OS X to, respectively, capture a full screen screenshot and capture a Selection screenshot. Thus you could get some conflicts with these shortcuts in Mail. But you can still modify the shortcuts for the OS X stock “Grab” application.

Hiding the sidebar

The sidebar (officially named the Message Box list) can be hidden by pressing Shift-Cmd-M or using your mouse to reach the View > “Hide Mailbox List” menu command.

Gmail-like conversations

If you want email messages sent back and forth between you and others being grouped in conversations, as in Gmail, simply select the View > “Organize by Conversation” menu command.

Mail.app as a fullscreen app

You just have to press Ctrl-Cmd-F, or choose the View > “Enter Full Screen” menu command, to get a dedicated screen for Mail.app.

The final result: a cleaner Mail.app

Screenshot showing my customized Mail.app UI.

This is what my Mail.app window looks like after all these customizations.

Rules, Data Detectors and Mailbox Search are your best friends

Here are three more things you get with Mail.app that makes managing and processing emails easier:

  • Rules can be extremely handy. But my advice is not to use too much rules, otherwise you’ll spend more time dealing with them than actually processing your emails. I’ve set up just one rule that I’ve named “Trash!”. It triggers when I receive messages from specific email addresses that I can’t unsubscribe — or just have not taken the time to unsubscribe from — but don’t interest me. When the rule is triggered, the message is both marked as read and moved to the Trash. Simple.
  • Data detectors are a little treasure! Hover your pointer over date/time contained in the message body to show a little box with grey dashed-line borders.
    Screenshot showing data detected in Mail

    The little grey dashed-line appears when you hover text containing date and time. This indicates Mail has detected some data you can interact with.

    From now on, you can click on the little triangle at the right of the box and you’ll have the opportunity to automatically (magically?) add a new meeting in the OS X built-in Calendar, or Ctrl-click on this triangle for more actions.

    Screenshot showing the Add to Calendar action in Mail

    Mail has detected that the body of the email message contains some data that refers to an event, so you can add it to your Calendar with just a click. Notice that the subject of the email has also been grabbed and added as the name of the new event.

    It also works with contact info, usually added in the email signature of the sender: hover your pointer over these info and add the info to an existing contact or create a new one with just a click!

    This built-in trick just saves me so much time! I haven’t seen any other email client such tighly integrated with Calendar and Contacts on the Mac. This clearly makes Apple’s Mail.app a winner, though I suspect developers of other mail clients can’t have access to these data detectors to implement them in their software, just because Apple does not allow it (yet?).

  • Rather than filing the emails I don’t delete into a complicated structure with folders and subfolders, I rely on the Mailbox Search (press Cmd-Option-F to access it, it is located in the upper right of your Mail window). It is really powerful since the Lion update and you can even specify you’re looking for contacts, dates, subjects, and more.


I definitely think Mail.app is one of the best tools to deal with emails on the Mac. Of course, there are other apps but this one is free and tightly integrated with OS X. I have developed my own workflow to deal with emails and I just can’t really use it with other email clients, because they lack multiple colors for flags, smart mailboxes, data detectors and rules.

This does not mean I don’t need a bit more, and, for instance, in the next iterations of Mail.app, I think cloud storage integration would be a real plus: simply drag and drop an item from your Dropbox folder to the body of a message and a share link is automatically created, as you can have if you use Sparrow. That said, it’s not way too hard to upload a file with CloudApp, Droplr, or Dropbox, and then share the link in your email.

What do you think about all of that? Do you use Mail.app? Have you found another email client that fits your need? Feel free to share your thoughts, tips and workflows in the comments below.


Add Yours
  • I am using Sparrow but after reading this article, I decided to give Mail.app a try. Your workflow seems really good. I really liked the idea of flagging messages. But I didn’t get how you use “Today” smart mailbox. Are you filtering messages that needs an action today or messages that were received today? Can you explain “today” a little bit.

    There is one small typo. You use Cmd+[number] to show a favorite mailbox instead of clicking Shift+Cmd+[number] (at least on my Mountain Lion).

    Thanks for this beautiful article.

    • Thanks a lot for your comment!

      Well, two things:

      1) the Shift+Cmd+[number] is not really a typo. In fact, I use a French keyboard, and we have to press Shift to type a number. I know you don’t need that on an English/US keyboard, I should have mentioned it.

      2) Today is, if I’m not mistaken, a Smart Mailbox that is already set by default in Mail.app on Mountain Lion. It simply contains messages received today. Actually I don’t use it a lot. But sometimes it is helpful.
      Setting due dates for messages that need an action is difficult in Mail.app without a third-party app. I don’t even think it is possible.
      Anyway, if you’d like a more “todo-based” approach, I greatly encourage you to wait for the release of the Mac client for MailPilot, that I will probably review as soon as it gets out of beta.

      Again, thanks a lot for taking the time to read this long article and comment it. I’m glad you liked it ! If you have any other question, feel free to ask! ;-)

    • in order to create ‘Today’ mail boxes which simple contains the last 24hours emails, follow below:

      Mailbox > New Smart Mailbox…

      Name it “Today”.

      Contains messages that match -all- of the following conditions:

      Date Received > Is today

      Click OK and you’re done!

      While exploring the rules options you discover many cool and useful features which actually super easy to understand.

      Enjoy! :)

  • I’d consider giving Mail.app another shot if only you could stop it from making attached images inline. This particular issue drives me nuts and is the reason I still use Postbox (which isn’t ideal but for me represents the best of a bad bunch).

    How’s Gmail/Google Apps sync in Mail.app these days?

    • I use four accounts in total (1 of them Gmail and another GApps) and it works great. Searching “All Mail” on the server works well too. I rarely use Gmail’s web interface anymore. Ever since version 6.x of Mail.app in OS X 10.8 I’ve been very satisfied.

    • About inline images, just run the following command in the Terminal:

      defaults write com.apple.mail DisableInlineAttachmentViewing -bool yes

      (Source: http://micahgilman.com/play/disable-mac-mailapp-inline-image-attachments/)

      Hope this helps!

      About Gmail sync, it works great, nothing more to add to what Jon Henshaw wrote ;-)

    • To stop Mail.app from showing images and PDFs inline, you should get Attachment Tamer.


      • Thanks, I didn’t know about this one!

    • dixhuit, You don’t have to worry about Google Apps it still works with Mail.app there is nothing to worry about it and it works same as the Google Mail. I haven’t experienced any issues with Google Apps and the Apple’s Mail client it works perfectly for daily use.

      • Same here!
        Thanks for your comment, Dominic.

  • Mail.app is definitely superior with the latest version of OS X. I just created similar filters a couple days ago, so it was freaky to see you listing almost exactly the same filters I made ;)

    In my experience, Mail.app handles multiple accounts and searching the best. That’s one of the main reasons I stick with it…speed.

    • Thanks for your comment, Jon.
      Glad you liked the article, Jon, and glad to know that we use the same workflow!
      Totally agree with you. Mail is really speedy, and I never felt the need to compress mailboxes as it was the case with Thunderbird.

    • One of the reasons I switched to Gmail webmail from Mail.app was to avoid the gigantic mail stores kept locally on my HDD. I found it slowed down my machine. Unless there’s a way to switch off local storage?

      Other reasons I switched were:

      1. ‘Undo Send’ for up to 30 seconds with Gmail Labs, which I use several times per day after sending a message then realising there was a mistake!

      2. Search – it’s far quicker than searching local hard drive.

      If anyone can convince me to come back to Mail.app I’d be happy to listen – I much prefer native apps but the benefits of Webmail are keeping me away.

      • I agree with Charles.

        I avoid Mail.app for the exact same reason as I do not want hordes of email stored on my HDD. I use Mailplane (beta 3 = huge improvement) to solve this as it offers a nice wrapper around the Gmail interface.

        • Thanks for your comments, Charles and Simon.

          Indeed, having huge email libraries *might* be a problem… except for me. My Mail.app library is of moderate size, mainly because:
          – I delete a lot of emails
          – Emails containing important information are actually also deleted after I’ve copied and pasted the information in another notes app. I use nvAlt to store hundreds if not thousands of plain text notes. nvAlt *is* built for this ;)

  • I never thought about using smart inboxes, then adding them to the favorites so I could remove the sidebar. Awesome idea; thanks.

  • Well, I see the potential of mail.app, and I just love the speed and clean interface (MS outlook is just plain ugly) But, and this a big problem for me, somehow mail.app destroys my e-mail templates. I use a nice html signature, and somehow my send e-mails look crap in outlook or webmail. The fontsize is wrong, spacing is wrong, it just looks, ugly. And MS Outlook, well, the client is not pretty, it is not fast but it does send out nice looking e-mails to my customers! I really hope Apple can fix this, when they do, I’m back at mail.app.

    • Thanks for your comment.

      I don’t meet this problem as I only use a plain-text based email signature ;-) This way, it never looks messy. It looks a bit old-fashioned, though! Haha

      Hope Apple will fix this for you in a future release.

    • I have an HTML signature with mail.app
      I used the solution described here (sorry, it’s in french)

      • I’ve got a HTML signature too, but the e-mail itself still looks bad on windows pc. The fontsize is wrong. For instance, my HTML signature and e-mail text are all Arial 12. On a windows pc it looks like the text is arial 9 and the HTML signature looks like Arial 14!

  • Thanks for your article, it gave my some new ideas =)

    But I can’t seem to find a way to make a smart mailbox for the unflagged mails. I can’t also make a smart for attachments, “Contains Attachments” doesn’t work.

    • Thanks, glad I helped you!

      This “Unflagged” Smart Mailbox is a bit tricky. Indeed, you can’t simply use a condition “Message has no flag” in Mail, this condition does not exist!

      Instead I actually use several “Message is not in mailbox” conditions, making sure I add a condition for each Smart Mailbox that works with a flag ;-)

      My “No Flag” Smart Mailbox is setup like this:


      Hope this helps! Feel free to ask any question.

  • I had a similar setup to the one you are describing, not so much inbox zero as inbox everything. Makes perfect sense but the lack of support for smart mailboxes on iOS drove me nuts after a while, so for the time being I am using a single archive folder for mails that have been dealt with. Hopefully iOS 7 will bring some improvements in that department.

    • Thanks for your comment, Simon! And thanks for sharing your workflow on iOS. Indeed, Mail on iOS is largely inferior to its OS X counterpart and I have great hopes for iOS 7.

      One of the big problems, indeed, is that there is only one color for flags on iOS… Hopefully, even if all flags look red on iOS, colors are preserved on OS X.

      My own workflow on the iPad (I don’t have an iPhone anymore) is much lighter than on OS X.
      I don’t really process emails on iOS, I only read new ones and decide what to do with them:
      – I delete a message if I don’t need it
      – I don’t add any flag on iOS: if a message needs a flag, I forward the email to another email address (this latter address is not in the accounts on the iPad, only in the accounts on my iMac and MacBook) then delete the original message on iOS so I won’t get double messages back on my Mac ; appropriate flags will be added when I’m back to my Mac
      – similarly, if a message asks me to do something, I simply forward it to the previously mentioned supplementary email address, and when back to OS X, I will use the “Add to TaskPaper” service for this email

      Basically, actually, Mail on iOS is only for writing new emails and doing some quick decisions about new incoming messages.

      Hope Mail in iOS 7 will be greatly enhanced! I miss my Smart Mailboxes and my colored flags…

      • I was wondering the same issue, syncing the OSX workflow with iOS and just realize that we could use this workflow in Gmail using its labels. Yes, I know, then we’ll be working online (not locally) but it’s a good way to keep syncronized all devices. Indeed, the last Gmail app on iOS is really good.

        About Task Management, well, you could just copy the url’s message and paste it on your Task Manager.

        • Exactly, Carles, you could have almost the same workflow I described here with Gmail. But I prefer to use Mail.app anyway, UI-wise. Your mileage may vary.

          About working offline with Gmail, I’ve read a few years ago that you can work offline (http://gmailblog.blogspot.fr/2009/01/new-in-labs-offline-gmail.html). I don’t know if you can still do that, though, because I don’t need it.

        • Since you can access Gmail labels via IMAP, one could replicate your workflow in Gmail AND still use Mail.app on the Mac. Just create favorites of IMAP folders instead of smart mailboxes. Am I mistaken?

  • I’ve switched to Mail.app because it has the most reliable integration with Notification Center. I primarily use Gmail, so that’s the account I have in Mail.app but one thing that consistently happens is my e-mails won’t send (to the point where I read e-mails in Mail.app and pull up gmail in a web browser to send them). Know how to fix that?

    • Renee, are you sure the configuration of your Gmail account is correct? Usually, when you add a Gmail account, you only have to enter your name, email address and password and it is automatically configured. But it seems something strange happened here with your account.
      The server used to receive incoming messages is not the same as the server used to send messages. In your case, it seems that there is a problem with the sending server (also called SMTP server).
      See this link for more info: http://support.google.com/mail/bin/answer.py?hl=en&answer=78775

  • Nice article, it gave me some ideas for ways to improve my workflow in Mail. Thank you for sharing your workflow and for giving examples and instructions on the setup!

    • You’re welcome, David, thanks for your comment, glad you liked the article!

    • i can only second this. the most useful article i’ve read so far here. thx for giving us impulses!

      • Thank you very much, Phil! I really appreciate that.

  • I wouldn’t mind giving Mail.app a try again. But it still struggles with Gmail/IMAP and adding a picture to an email seems to result in a nasty memory leak and eventual crash. Even the ‘geniuses’ at the Apple store conceded defeat and admitted there were faults in the latest version of Mail.

    So I have switched to using Mozilla Thunderbird. At first I was not sure, but now I really like Thunderbird and have found it to be absolutely rock-solid and works perfectly for my needs. A few extra free plugins like Conversations, gContactSync, MoreLayouts and DropBox FileSync have enabled me to do more with Thunderbird than I managed with Mail. In my opinion, Thunderbird is worthy of a second look.

    • Hasn’t Thunderbird development been discontinued?

    • Thanks for your comment.
      As Phil wrote, the development of Thunderbird is now discontinued.
      I’ve never had a big problem with Thunderbird, except that, to my knowledge, Thunderbird does not support data detectors as in Mail.app. This little drawback is a no-go for me, but of course your mileage may vary ;-)

  • I really like the idea of this workflow. One thing I am curious about is whether or not you still use regular folders for clients, projects, etc., or you just leave everything (once processed) in your original inbox.

    If you were to login to your Gmail account and opened Inbox, would you have thousands of read emails sitting there?

    • Thanks for taking the time to read the article and comment it. You’re identifying some important aspects of my workflow. The article already was a long one, so I didn’t want to get too much into details but I’m glad you give me the opportunity to give some more clues.

      To quickly reply to your questions, I don’t use any regular folder for clients, projects, etc. … *in Mail.app* (see below for more explanation).

      And yes, when I login to my Gmail account, theoretically there could be thousands of read emails, except that I asked Gmail UI to show me Unread emails first, and read emails are in the folded, out of sight “Everything else” category. Also, I delete a lot of emails. So there is not much visual clutter, it is exactly the same as with my Unread Smart Mailbox in Mail.app: I only see new, unread, unprocessed emails when I’m in Gmail.

      Another key aspect of my workflow is that any email client I use is just a medium: it helps me see what’s coming in and helps me send things out. I don’t store information in my email archive in the long term, that’s why I wrote in the introduction that I don’t consider email clients as a filing cabinet.

      As robust as Mail.app is, I don’t entirely trust the ‘every emails in a big database’ concept. If your database gets corrupted, you could lose hundreds of important emails (that happened to me when I was still using Thunderbird on Windows years years ago…).

      So, except for the temporary information contained in my “Follow up” folder, I get every important information and documents *out of Mail.app*. I archive important conversations with clients by copying and pasting the text into plain text files that are easily accessed through the excellent nvAlt. Also, same as for Mail databases: in nvAlt I chose to store notes as individual plain text files, and not let all notes be stored in the same database as it is configured by default. The folder where these text files are stored is a Dropbox folder so I can access my notes on the go and read them either with Dropbox itself (the iOS app previews .txt files right in the app) or with any iOS text editor I need on my iPad.

      About clients and projects, I have a big folder simply called ‘Projects’ that was previously also stored in Dropbox but is now on my personal NAS at home. This ‘Projects’ is a big bucket where I store attached documents found in email messages. This folder thus contains every document for every project, all without subfolders. But I have a very specific convention for naming my files and I rely on it and on “Saved Searches” from the Finder to find the files I need. (I also use the same convention to name my text files containing archived conversations in nvAlt)

      Generally, I feel that smart folders / smart inboxes / saved searches and everything that is ‘smart’ is more flexible than a complicated hierarchical subfolders structure. With the really decent hardware that Apple offers these last years, relying on search is often quicker than browsing the Finder. But you have to be really specific about how your name your files.

      Once conversations are stored in plain text files and attached documents are extracted from email messages, in fact I generally delete the original email once it is not in my “Follow up” Smart Mailbox anymore. So it won’t clutter my email archive, keeps Mail.app databases relatively light and does not clutter Gmail!

      I hope my explanations help you. Thanks again for asking!

      • That is the killer info that I was looking for, thanks! This is very useful information.

        Do you have an article on nvAlt yet?

        • Not yet, Phil, but I plan write to one, someday, here ;-)
          What specific items would you like to be covered?

        • Maybe I don’t need an entirely new article, but could you detail your naming conventions for us now?

          I’ve struggled with email/task organization for a long time, even with aids like the Things app, etc. So I’m about to take the plunge and follow your article step-by-step.

        • Well, my naming convention is actually a rather complex system, and the best is to find your own! ;-)
          I was inspired by Douglas Barone (http://dougist.com/2009/08/file-system-infobase-manager/) who himself was inspired by someone known as ‘AmberV’.
          You should definitely have a look at his article, it’s long, very detailed and full of ingeniosity.

          In short, the name of all of my files, everywhere on my harddrive, and thus in nvAlt too, looks like this :

          [date and timestamp]-[code in my own classification]-[other information depending on the type of document]-[File_title_with_underscores]

          For instance, this article published here was named
          “13-0112-172248-C2EBD-MacAppStorm-Customizing_MailApp_and_my_workflow_for_emails.txt” on my harrdrive.

          Underscores are here just because I use a Linux-based NAS with EXT4 filesystem, so avoiding spaces in names is important.

          The first part, “13-0112-172248”, is for a date/time stamp in the YY-MMDD-HHMMSS,
          which means that this file was created at 17:22:48 (in French, which means 5:22PM and 48 seconds).

          The second part “C2EBD” is one of the numerous codes I use. C means Creations, 2 is for Professional (1 would be for Personal), E means “Ecrite” in French, that is “Written” in English, B is for Blog, D for Draft.

          This way, by typing just C2EBD in nvAlt or searching for files containing this in their name, I instantly find blog drafts for professional (freelance) use!
          If I want to narrow my research to only drafts blogs written for MacAppStorm, I type C2EBD-MacAppStorm and I’m done!

          In fact, my “code” is like a deep folder architecture. First, a general category, then a sphere (personal or professional), then subcategories.

          This gives really long names. It is not really easy to deal with in iOS, but all apps I use on iOS have a search functionality, so by simply searching for “workflow” or “workflow_for_emails”, I find the file quickly.

          For a given project for a given client, I use the same client name and the same project name. This way, searching for “MacAppStorm-Customizing_MailApp” in the Finder instantly gives me all files with this in the name, that is all files related to this little project (writing an article about Mail.app for Mac.AppStorm) should it be the general .txt file, images (screenshots), PDF files and other research material if needed.

          Hope this helps!

          You will also find other useful information and strategies by reading some 43folders articles (from Merlin Mann) like these ones:

          PS: by the way, I don’t type the date/timestamp by myself, I use TextExpander for that ;-) I simply type “ts;;” and it is automatically converted into YY-MMDD-HHMMSS-

          In fact, for some kind of files I create often, I’ve even created special snippets in TextExpander. For instance, to name a new blog post, I only have to type “nwbd;;” (nbd as in ‘New Work-related Blog Draft’) and a TextExpander pop up window appears, YY-MMDD-HHMMSS-C2EBD- being automatically filled; the popup just asks me to fill which blog the draft will be published in and the working title of the article.

          I will probably reveal some useful tricks like this one in a forthcoming article about TextExpander ;-)

      • I’m very Interested on Files Name condification (sorry, I can’t reply the last reply below).

        In your example, you use C2EBD (creation,professional,ecrit,blog,draft). Has this code 5 characters always or is it mutable?

        I mean, you use this characters like labels? You can just use C2E or add new ‘features’ to this code.
        And is the order of the characters important? Could you use C2DBE.

        I wondering this because it could be some chaotic, at least when you’re looking for some files. For instance, how do you search all your drafts? I guess you use queries like that “*2*B*D” for professional blog drafts, don’t you?

        Greetings from Spain.

        • Thanks for your interest, Carles.

          My code as, at the very least, one letter and one number.
          For instance, I tend to write down a lot of lists for all sorts of things, so these lists are L1 and L2, depending on whether they are personal or pro.

          Most of the time, the code has three characters, letter-number-letter. But sometimes I go deeper with more characters, as in C2EBD. I’ve never used more than 5 characters.

          However, the order of the characters in the code is **super important** in my case. I try to avoid codes that are too similar and could lead to mistyping and then misclassifying: I mean, actually, I don’t have C2BED, but if it existed, it would be something different from C2EBD and not to be confused with.

          Searching for all blog drafts, whether they are pro or personal, is just searching for EBD- (either in nvAlt or in the Finder). The dash is important here as it means that it is the end of a code. I never use several uppercases in a row in the file ‘title’ (the last part of the name of the file), so using uppercases and dash guarantees that I will find what I’m looking for.

          Searching for all professional blog drafts is just adding one more character before: 2EBD-

          I don’t need the wild cards * because, while adding or deleting some codes over time (my system is not completely fixed yet), characters are not interchangeable and their order is, as I already wrote, important and conveys some meaning.

          Hope this helps.

          I’m starting to think I might write an article about my classification code. But I’m not sure Mac.AppStorm is the place for that. I have to see that with my editor ;-)

        • (My code *has […] one letter and one number.
          Of course! Sorry for the typo!)

        • Another precision: I use dashes and not underscores between the date, the code, and the title. This is because navigating with the keyboard within the name of the file is easier like this: with Alt-left/right arrow, you go from one block before/after a dash.

          Let me explain: if the name of the file is 13-0121-134058-C2EBD-MacAppStorm-Customizing_Mail_App_and_my_workflow.txt, if you place your cursor at the very beginning and press Alt-left arrow several times, you will go at the end of 13- after the first press, to 0121- after the second, to 134058- after the third, and directly before the dot (before the extension) after the fourth press on Alt-arrow.
          Might be useful in case you need to rename some parts of your files.

      • Hi Pierre,

        Good stuff! I am right there with you on smart mailboxes with lots of rules that make them close to ideal. I also renamed the flags to what they mean to me and put them up in the toolbar.

        One correction, if you’ll allow it: Mail.app does not use a database of emails. I think it never has. Mail has an index of emails, but the emails are stored on disk in a nested folder structure — so you never need fear losing emails due to database corruption. It’s actually quite handy for archiving purposes because while an email can be “not visible” within your Mail interface, Spotlight can still find it and when selected in Spotlight Mail will open it up just fine. I “archive” mail by year and at year-end drag the folder for that year out of Mail to an external drive.

        • Thanks for the precision, Jim, I was not aware of the way Mail.app stores the emails.

  • Good ideas Pierre! You’re making me rethink my own workflow.

    • Thanks, Reid! I’m glad I can give you some inspiration :-)

  • The “Organize by Conversation” of Mail is so much better than on all the alternatives (Gmail, Thunderbird & co.) I wished they add the “Quick reply” killer functionality of Postbox.
    I’m an inbox zero fanatic for a long long time and I share a similar workflow with a specific time to check email, direct decision, Mail.app in full screen with no sidebar, no folders and subfolders, only favorites smart boxes, keyboard shortcuts and Taskpaper (that I must have discovered through Appstorm, and I can’t thank you enough for that!)

    From the Inbox, mails goes to Archived or are flagged Red (called “Today”, equivalent to your “Need reply”) or Grey (called “Later” equivalent to your “Follow up”).
    By using the flag Red, I can keep the same workflow and an inbox zero on iOS. Mails are archived or deleted or flagged Red, then when I get back to my desktop I check the “Today/red” smartbox and change some messages to grey if needed.

    • Thanks for sharing your workflow, Greg.
      Really clever suggestion here! This might make me rethink my workflow for a smoother transition between iOS and OS X, thanks again!

  • I don’t get everyone’s “need” to have an empty inbox. Who cares if you collect a lot of emails over time? If you need to find something, use the search function. That’s what it’s for. I have a hundred or more emails in my inbox and i never have any trouble finding one if i need it.

    • I can understand your opinion, Jeremy.

      I just don’t like visual clutter. I have no problem finding emails. But what I have a problem with is looking again and again and again at the same inbox where unread and read emails are in the same place.

      “In real life”, every evening when back from work, I empty my physical mail box, the one the postman fills up everyday at a given time. I don’t let letters fill up this box. I simply do the same for my emails ;-)

      I really need to have a clean, email inbox. Otherwise, the emails I’ve already read will probably distract me when I check for new messages.

      You know, I somewhat think this debate is related to the point of using a minimalist text editor versus a full-featured word processor.

      But, again, thanks for taking the time to read the article and sharing your point of view!

  • Thanks for the great tips. I read recently another post on the ‘unread’ smart mailbox but yours prompted me to set it up. What I like best is using the usual inboxes as the ‘archive.’ I had long used ‘trash’ as the archive once I processed the inbox messages. This arrangement allows me to neatly divide the real (delete forever) trash from the messages that I might not want to see again…but just might.

    • Thanks for your comment, Mark.
      That’s exactly how I use the usual inboxes and the ‘trash’!
      I’m glad I prompted you to make it, inspiring people makes me happy!

  • Hi Pierre,

    Thank you very much for a great article. I rarely leave comments but wanted to drop a note, the usage of mail.app here and the subsequent ideas in the comments are a huge help. I have been “unhappily” using Outlook 2011 for a while now and daily looking for new email apps, I have begun employing many of the tips you laid out here and am jumping back over to the built in mail application.

    Oh how I have missed its speed!

    Just need to take some time to spruce up the layout a bit, kinda small and bland for me ;)

    Thanks again!

    • Thank you very much for commenting, then, Ryan!

      Yes, I appreciate the speed of Mail.app and its tight integration with OS X everyday!

      About the layout, yes, I love things minimal and uncluttered. But the best is that Mail is really flexible and customizable in terms of UI.

  • Thanks so much for this article and the tips! (I found it on Zite.) I’ve followed your instructions and love the look of my Mail app now! Looking forward to seeing how it works this week and, perhaps, what needs tweaking.

    I’ve been implementing the “Secret Weapon” methodology with Evernote, so I have a new Smart mailbox called “Send to EVERNOTE” and will try a batch action when needed. If you’re interested, you can read about it here: http://www.thesecretweapon.org


    • Thanks Martin!

      Yes, I’ve heard and read about The Secret Weapon several times, I think I might give it a try soon. I’m not a big fan of Evernote, though, and only use it to archive things that, frankly, I never use/read/open again! Haha.

      Thanks again for taking the time to read this long article and for your suggestion.

  • Thanks for a great article. I’m a bit of an email client junkie. Always try out everything I can find, and have yet to find the perfect one. This article gives me hope for mail.app (which I tried again recently, but didn’t spend the time to set up this type of workflow on it).

    Just a question, though. Do you know of a place where there is a collection of plug-ins or extensions for mail.app? There is one or two things that I miss still, and would love to see if there’s something out there.

    • Thanks for your comment and for reading the article in full, Henk!
      About plugins, when fiddling with my workflow and setup years ago before going back to strictly built-in features, I found this collection of Mail plugins really helpful:
      It seems the website is a bit dated now, so I’m not sure the plugins still work with OS X 10.7 and 10.8, but you might give them a try ;-)

  • Hey Pierre,

    I’ve said it before but I’ll say it again… Great article mate!

    Now, to light a little fire here ;)

    The workflow you’ve described is indeed great and very flexible, but I personally am having a hard time straying away from Postbox. While not the best out there, it does allow for a workflow very similar to this and at the same time provide additional features which are to me, a time saver.

    Topics: You can assign topics to emails, very similar to gmail labels and then setup smart mailboxes for topics.

    Keyboard shortcuts: I can very easily move emails to specific folders with just a few keystrokes, archive emails, flag them and much more.

    Grouping of accounts and a more segmented view of each is fundamental. I currently have 6 accounts configured in postbox and the view is never cluttered, whereas in Mail.app it quickly becomes unwieldy.

    Nonetheless, great ideas for some innovative workflows for dealing with mail mate!


    • Thanks for your comment, Pedro!

      I’ve had some sort of love/hate relationship with Postbox. When I was still on Windows, I felt in love (OK, well, it was just a software, but… haha) with Thunderbird. Postbox is based on Thunderbird, right?
      When I switched on the Mac (for the release of Leopard, approximately), I was a bit hesitant about Mail.app. Definitely, before Lion, I had a hard time using the built-in app, that I couldn’t customize enough. So I installed Thunderbird. And then Sparrow. And then Lion came out and I was blown away, the new Mail UI was so much more appealing than previously!

      I’ve tried Postbox, but, just as you are having a hard time quit using it, I have a hard time quit using Mail.app! haha

      I don’t use Gmail labels, that’s probably why I don’t need anything related.
      Also, I don’t really need to know to which of my several email addresses the email was sent, as I wrote in one of the comments, I get all that I can out of Mail.app and file it to the appropriate spheres (personal or pro) and projects elsewhere.

      Anyway, at the end of the day, the best workflow is the one that fits your needs! Thanks for sharing a bit of yours, here, mate! ;-)

      • (*switched to the Mac… if you could correct this, Matthew, thanks!)

  • I have a simple system for keeping a zero inbox (or close to it). It’s more of a philosophy than a system:

    Rule 1: Everything in my inbox is complete and total shit, unworthy of my attention.

    Rule 2: If an email in my inbox does not fall under rule number one, then I respond immediately.

    Rule 3: If I simply cannot respond immediately (follow-up items), then I either consider them to fall under Rule #1, or move them into an Act-On Mailbox that gets auto deleted every 2 days, with the idea being that if I can’t respond in two days then it must not be important—which means it should have fallen under Rule #1 to begin with.

    See the pattern there? And guess what… the world continues to turn. ;)

    • Thanks for your comment, James!

      Neat and simple system, yes! Maybe is it the ‘extreme’ I’m trying to reach ;-)

      Thanks for sharing it with us.

    • Also, your system is somewhat Asimov-inspired ;-) I like that.

  • I gotta say that you left off my favorite, must have feature, that so far no other mail client will do – Show Contact Photos. Its in preferences. To be able to view your email list by image is wonderful. It makes it so easy to see at an instant who an email is coming from, and also to quickly find an email. That feature along with something like Cobook are great, and now that mac address book will bring FB and other images for contacts, I suppose Cobook is really needed, but I still prefer it.

    • Oh, now that’s one feature I missed from Sparrow. Awesome.

    • Oh, yes, I’ve never been aware of this one! Thanks a lot, Micah, really helpful!

  • first: thank you for a totally inspirational and enlightning article!

    second: i’m having troubles with apple mails built in spam filter post the tweaks; the messages tagged [spam] are not moved to the spam mailbox – probably because they are marked “unread” and thus end up in my supposed-to-be-inbox-zero. i’ve tried all possible combinations of “advanced” rules in mail preferences with no luck.
    did anyone else experience this/ find a solution? or: maybe there are better ways (eg. 3rd party filters) to get rid of spam?


  • Thank you for your compliment, Fred, really glad you liked the article and found it useful!

    Indeed spams are one of the big problems with Mail.app, and for a lot of people, the built-in antispam filter is not efficient enough.

    If you want to use it, my advice is to make sure that, in Mail.app preferences > “Junk Mail tab” you:
    – Enable junk mail filtering
    – for “When junk mail arrives”, choose “Perform custom actions”
    – click on the ‘Advanced…’ button and set the “Perform the following actions” as:
    – “Move Message” to mailbox: Junk
    – “Mark as Read”
    – and if needed, “Set Color” “of text” to the color you want

    That way, you should not have too many problems if your spam volume is acceptable. At least it worked for me.
    Unfortunately, you still might get some false positives and false negatives, at times, and the antispam filter will need some time to learn from your emails.

    If you need a third-party antispam, it looks like SpamSieve is one of the best on the market:


    John Gruber himself and several other renowned Mac bloggers consider it as the best antispam available for Mac.

    As I haven’t received that much spam these last years, I was having a hard time spending $30 on an antispam filter, but it is really worth it if you need it, I’ve been told several times.

    Actually I’m currently trying the free demo (30 days) mainly because I’m more annoyed by the false positives than by the false negatives ;-)

    Hope this helps!

    • Thank you for your answer – and your thoroughness, Pierre; it’s much appreciated! After much ado i found a solution to my overwhelming spam-issue.

      My Unread-mailbox needed an extra rule:
      Message is in Mailbox > Inbox = True

      Before that rule was applied the Unread-mailbox pulled all the spam/ junk from every source possible. An extra “mark as read”-rule in the built in Junk-mail handling system did not do the trick.

      Maybe obvious, but i pulled my hair for a while.

  • Nice article. How do you get around the gmail archive vs. delete options on Mail? If that was possible, I might do it!


    • Hi Bob, thanks for your compliment and for the question.
      As I almost never use the Gmail web interface, I was not aware of that archive/delete problem; when I use Gmail on the web, I only see messages that have not been read yet in Mail.app, and that’s all I need.
      However, I did some research and found this really well-crafted tutorial:
      I’ve just tested it out and it works as advertised.
      Hope this helps!

  • Hi Bob, thanks for your compliment and for the question.

    As I almost never use the Gmail web interface, I was not aware of that archive/delete problem; when I use it Gmail on the web, I only see messages that have not been read yet in Mail.app, and that’s all I need.

    However, I did some research and found this really well-crafted tutorial:


    I’ve just tested it out and it works as advertised.
    Hope this helps!

  • Hi,

    Thanks, I liked your article.
    Perhaps this is a topic for another day, but how about stationery?
    I really like Mail.app, but I never found a way to set default stationery, neither for new messages nor for replies.
    If you can enlighten me, I’d very much appreciate it.


  • Great tips.
    I’ve used Gmail web interface for so many years. I’ve never get used to Mail.app since it never satisfied my needs.

    I’m giving a second chance to Mail.app thanks to you :)

    • Thanks for the comment! Really much appreciated :-)

  • Hi Pierre,
    thanks for the inspiration! I’m trying your system out since a few days and already liking it.
    I often read e-mails on the go on my iOS-device and then often forget about them, as I didn’t highlight them.
    This is how I am tweaking around this:
    iOS is able to flag a message, but only ever highlights it as “red flag”.
    So I set up a smart mailbox that filters for red flags and named the mailbox “Review”. Once home, I open the “review” mailbox and sort the mails it into the correct category (e.g. ToDo, follow-up, reply).
    This is pretty much the system you described above, only that I don’t have to forward to a separate e-mail account. Obviously, I have assigned other flag-colours to my other smart mailboxes, as “red” is now reserved for “review”.

    • Hey, Stefan, thanks a lot for this comment!
      Your solution is so easy and straight-forward that it makes me a bit jealous of having not thought about it earlier! haha ;-)
      Sometimes, I miss simple things… Thanks again!

  • I love your ideas about using the Mail.app, but it doesn’t seem to work so well if you sync your mail accounts with your iPhone. If you read an email on your iPhone it will not show up in your “Unread” smart mailbox and all your flagged messages are no longer color coded but just dumped into the “Flagged” mailbox on the iPhone.

    Do you have any suggestions as to how you can make your workflow compatible with someone who uses their iPhone to handle mail in synchronization with their Mac?

    • Thanks for your comment and your question.
      Yes, I’m aware this does not really work well in conjunction with iOS Mail.

      About the fact that emails read on iOS won’t show in the “Unread” inbox on the Mac, it’s by design! My workflow is designed to spend the least time possible on reading/dealing emails, so I don’t want to read an email twice!
      However if you still want to have some emails you already read on iOS to be considered as unread on the Mac, I simply suggest you mark them unread again on iOS after reading them. I won’t do that as it would defeat the purpose of my workflow, but your mileage may vary ;-)

      About flagged messages, yes, I know, unfortunately you only have one color for flags on iOS. Don’t worry, though, emails you add a blue/green/whatever flag to on the Mac will preserve the color of their flag wherever you read them. They will simply appear to have a *red* flag on iOS (as it is the only color available there) but the *real* color will appear back on your Mac. A side note: if you use the Gmail web interface, messages with a colored flag will appear starred. Again, this does not interfere with colored flags on the Mac.

      My advice is:
      – not to change the flag on iOS if you don’t want it to be converted to a red flag back to your Mac
      – use the really neat workaround Stefan suggested, in the comment just above yours: as he wrote “iOS is able to flag a message, but only ever highlights it as “red flag”.
      So I set up a smart mailbox that filters for red flags and named the mailbox “Review”. Once home, I open the “review” mailbox and sort the mails it into the correct category (e.g. ToDo, follow-up, reply).”

      Hope this helps. Feel free to ask any other questions.

  • Great post. I had a similar set-up, but not nearly as streamlined. I’m going to work my way through your suggestions.

    One question. I access mail from two machines, one at work and one at home. I know that the smart mailboxes etc are supposed to replicate from one to the other, but have had problems with that in the past.

    Can you suggest a way to ensure that the set-up is identical on both machines?


    • Thanks for your comment and your question, Jeremy.
      Well, I have three machines (two iMac, one at home and another at work, and a good old white MacBook). MobileMe used to sync smart folders and rules and it worked well for me. Unfortunately Apple removed these features from iCloud.
      I don’t have any solution other than manually setting these smart inboxes. However, because I don’t use that much and they are pretty simple, this should not take too much time ;-)
      Also, I found that having to set it manually for each machine made me rethink a bit my workflow and adapt it to the context: for instance I don’t read personal emails at work and I don’t read work emails at home. So setting up a slightly different UI, workplace and workflow might be useful.

  • Hello Pierre,

    It is great that this article of yours receives so much attention — I haven’t seen so many comments on Mac Appstorm for quite a while! Your tips and tricks regarding Mail.app are really unique. I am using Mail.app myself and have been reading and thinking a lot recently about how to set up an optimal workflow. I got me at lot of plugins, MailTags, Mail Act-On, MailHub, MsgFiler, and a few others, have created a lot of smart mailboxes, rules, keyboard shortcuts, a taxonomy for naming projects and tags, and I do feel in better control now, but my system is still too complicated to be really efficient.

    Your article was an eye-opening read for three reasons:

    First, I am amazed how much you were able to accomplish with just the standard features of Mail.app and OS X — your system is intriguingly simple.

    Second, your suggestions of using an “unread” smart mailbox for the “inbox zero” objective is outright brilliant. This makes sure that I get to see every new message only once, and it forces me to either get done with it or classify it right away. I also like that messages can now stay in the real inbox while I am not done with them — this frees me from having to move them to some other folder just in order to reach the “inbox zero” goal, and it also makes sure that nothing important can “slip through the cracks”, as going through the inbox will be part of my weekly reviews.

    Third, I like your suggestion of hiding the folder list. You are right, this unclutters the interface a lot, and accessing the folders directly is rarely needed anyway when having the smart folders up in the shortcuts bar. I didn’t really use the shortcuts bar until now as I was accustomed to accessing the folders through the folders list, but thanks to your suggestion I will now do it the other way around.

    Your suggestions also work well in the context of multiple “areas of responsibility”. I have three contexts into which all my emails fall, one private and two work related, and I like to separate those as I don’t want to deal with work related stuff during my free time and vice versa. So I now have two smart folders per area in the shortcuts bar: “new” is the “unread” smart mailbox, and “act” is a list of messages that I either marked as being actionable or which are to “follow up” and for which the tickler date has arrived (this is a feature of MailTags).

    Regarding the question of iOS interoperability: I own an iPad, an iPhone and an iPod and I do use these devices every now and then to read and (even less often) respond to emails, but the place where I really manage my email is my Mac. So I want to see the messages which I happened to read on iOS, and which I didn’t delete right away, in my Mac’s “unread” smart folder once again. My convention is that all messages need a reason to stay in my inbox, and this reason is indicated by message flags or tags. So I set up my “unread” smart mailbox to include any messages which are read but unflagged and untagged — these are exactly those messages which I read on iOS. I also use the red flag, which can be set from iOS, in a special way. Messages that have a red flag are “pinned” to both my “new” and my “act” smart mailboxes so they are guaranteed to be brought to my attention.

    Thanks again for your great article, and please go ahead and publish more about workflow efficiency!

    • Thanks a lot for your long comment! I really appreciate it. Indeed, my goal was to set the easiest system possible while making it the most efficient. True minimalism, would I dare to say ;-) Really glad you liked the article.

      Also, thanks for your suggestions for improving the iOS / OS X interoperability, really nice suggestions here, I’ll think about it! :-)

  • It took me forever to realize that you had a French keyboard and that you were actually using the flag color names and not being goofy. LOL.

    • Haha, yes sorry for that. Anyway, I don’t really know why, but while having set my first language as English to have screenshots understandable by and familiar-looking to our international readers, it looks like flag colors remained in French… Odd.

  • Fantastic article – implemented this today and it’s made a huge difference to my stress and workflow. Thank you so much for sharing!!

    • Thanks a lot! Glad it helped you transform your workflow.

  • Not sure if this has been mentioned, but to deal with the iOS usability issue, I have implemented your strategy using real (regular) mailboxes instead of smart ones. Instead of flags to sort the individual messages, I use simple macros in Keyboard Maestro to move them around, with keyboard shortcuts.

    Since my IMAP server lets me create any mailbox, I get the advantages of your method on the Mac, along with a reasonable way to do the same on my iPhone (with the folder-move icon on the iOS mail.app.

    • Nice suggestion, Alan! Thanks for sharing it.

  • Thanks for the detailed description of your workflow. I’ve already adapted it!
    One question so far: how do your sent emails fit in? Do you flag them, or just keep them in the Sent Items box?

    • Thanks for your interest, Gerrit.
      I sometimes need to keep an eye on important emails I sent. In that case I flag them with a green flag, so they show up in my “Follow-up” Smart Inbox.
      Most of the time sent emails simply are in the Sent Items inbox.

      • Still following your method Pierre, it’s working great!
        Meanwhile, I added one smart folder to sort e-mails I did read but didn’t flag. In fact, it simply reflects my Inbox without the flagged e-mails, the left-overs so to speak. Eventually they’ll end up in the Trash soon enough but there’s a certain “You never know” feeling about them.

        On my Mac, I also have a folder for this kind of stuff, calling it my “X-Files” ;-)

        • Thanks for your feedback, Gerrit!
          Looks a lot like my “Not flagged” Smart Inbox ;)

  • The main feature of the Mac mail.app that is missing for me is the ability to add alternating shading along with the thin lines for the message box. There was a simple app that did this in earlier versions of the OS X called ‘letterbox’ — but, sadly it doesn’t function on Mountain Lion. Is there another app out there or any way to do this ? This seems like a minor item but would really help readability alot as compared to the solid block of white background in the “classic” view (which I prefer) or only the line separators with solid white background in the modern view.

    any ideas ?

    • Thanks for your interest and question, Mark.
      Indeed, I don’t know a way to do this… I’ve done some research and found this old article:


      It dates back to 2007, so not sure it is still applicable. It involves having Xcode installed. I can only strongly recommend you *backup* your current Mail application by duplicating it before hacking it, though. No guarantee as I won’t test it by myself.

      Hope this helps.

  • Thx for this (not very new) great post. I setup all like you and love the workflow. Only one question: HOW have you setup the “not flagged” mailbox? I cant get it in the settings of the smart mailbox under OS 10.8…

  • Thanks for your interest, David!

    This one is a bit tricky.

    Below you’ll find the copied and pasted answer I gave to another reader in the comments ;-)


    This “Unflagged” Smart Mailbox is a bit tricky. Indeed, you can’t simply use a condition “Message has no flag” in Mail, this condition does not exist!
    Instead I actually use several “Message is not in mailbox” conditions, making sure I add a condition for each Smart Mailbox that works with a flag ;-)
    My “No Flag” Smart Mailbox is setup like this:
    Hope this helps! Feel free to ask any question.

  • One of my requirements is S/MIME support. So many of the 3rd party applications just don’t support integrating certificates for signing or encrypting.

  • Just a quick tip – I renamed each smart mailbox with the number so I can quickly reference it using CMD+#.

  • Mail is by far my favorite email client, but I haven’t been able to use it because our company uses Kerio, and the two seem to have conflicts.

    Has anyone been able to get the two to play nice within Mtn Lion?

  • Very nice advice! Indeed, OS X Mail is very good!
    But why is there no full threading in iOS’s Mail? Including sent mails…

    • Sadly, yes… Hope it will be featured in iOS 7…

  • Very nice workflow! I’ve started using aspects of it already. I particularly like how it cleans up the Mail.app user interface by using the favourites bar more efficiently.

    This workflow works even betterererer in conjunction with Alfred 2 beta and the Mail.app workflow by Pedro Lobo called spookily enough… ‘Mail Actions Workflow’. It allows you to navigate around Mail and also action emails via Alfred 2 beta.

    • Thanks!
      Indeed, Pedro is an Alfred and workflow genius ;-)

  • I stumbled across this post when looking for a better way of managing my emails. It seems like it’s going to be really helpful, thanks! I’m having trouble getting the email to taskpaper automator service working though… I get the growl notification that it was successful, but nothing shows up in taskpaper. Any thoughts on what I might be doing wrong? I’ve never used taskpaper before, but it sounds useful.

    • Thanks, glad the article helped you.
      I struggled a bit with having the script working correctly, too.
      Are you sure you have a “Project” called “Inbox” (case-sensitive) in your unique open document in TaskPaper? These are the pre-requisite (1/ have only one TaskPaper file open when triggering the script; the window might be minimized or hidden, though, 2/ have a project called “Inbox” in this file)
      Hope this helps.

  • Great info. One thing I miss is the satisfaction of seeing a message immediately disappear from my inbox as I flag it. And from my reply to smart mailbox as I remove the corresponding flag. Somehow smart mailbox views don’t auto-refresh. I have to change views each time and come back for the change to be reflected. Wonder if you found a solution to this. Thanks.

    • Thanks for your comment, Daniel.
      Indeed I also have this problem and I haven’t find a solution yet, except by switching views and come back, as you wrote.
      This is easily done with shortcuts like Cmd-1, Cmd-2, etc. though.

  • I really love Mail but I can’t understand why it doesn’t have the smart text and auto spell correct like my mail program on my iPhone. Does anyone know if there are any plug ins or anything you can do to add these features?

    • Mark,
      If you’re talking about the way “text bubbles” appear on iOS, if you have Lion or higher, you can have the same behavior. Go to Language & Text preference pane is OS X preferences, make sure you have, in the Text tab, “Use symbol and text substitution” and “Correct spelling automatically” both checked.
      Then, go back to Mail, and in the Edit menu:
      – make sure that, in “Spelling and Grammar”, “Check Spelling while typing” is enabled,
      – make sure that, in “Substitutions”, “Text replacement” is also enabled.

      That way, if you mistype a word, you should get a bubble with the correct word showing up. If you don’t click on the bubble and press Space, the word you typed will be instantly substituted by the text suggested in the bubble. If you don’t like the suggestion and consider what you typed is correctly spelled, click on the little cross right to the text in the bubble, just as in iOS.

      Here’s a screenshot of what happens if I mistype “texxt” on my machine: http://cl.ly/image/3y122n3F0C24

      Hope this helps.

  • Great concepts, and useful.

    However I have 2 problems:

    1. I cannot get the keyboard shortcuts to work. I’ve used OPT/CMD-V for VIP,
    and I was caeeful to use the same menu title for the keyboard shortcut in OS-X preferences as the smart mailbox name.

    Pressing ther OPT/CMD-V doesn’t set the flag… Am I doing something wrong?

    2. Also… since this didn;’t work, I QUIT mail and restarted, thninking it would make a difference. Well, ALL my custom smart mailboxes had disappeared. 2 hours gone down the drain…

    • Thanks, Steven.

      What is your OS X version and build number?
      I’m running OS X 10.8.2 build 12C60 and can’t reproduce what you have. Everything works fine for me, sorry.

  • I am going to give Mail.app another try after reading this as Outlook has been driving me nuts.

    One issue I’m having though, and maybe I’m missing something obvious: in my new smart mailbox of unread messages, the moment I click a message, it gets marked as read and disappears from the mailbox. How can I avoid this?

    • This is, by definition, the purpose of this ‘Unread’ smart inbox, Doug ;-)
      As written in the article, it forces you to act on your email as soon as you read it.

    • What did you use before Outlook? Entourage or Mail or anything? I really believe Entourage is superior to Mail.app >> Is Outlook not good?

  • Great tips you have given, I really enjoy implementing them.

    Want to check if you have any suggestions on handling attachment in Mail.

    Currently, I find it not as organise as Outlook, which there is a panel to view all the attachments.

    Any suggestions?

    Thanks in advance.

    • Just create a Smart Mailbox with the criterion “Has attachment”!

    • The tip given by reader ‘SP’ is all I can think about at the moment, Samuel. Thanks for your interest!

  • Hey, I like the ideas! It’s lessening the time spent fussing over 700+ emails a day and making me more productive.

    I’m having problems with the shortcut keys. It seems red is hardwired opt-cmd-r, and cannot be reset. I’ve had this type of shortcut conflict before. Is there some “master” list of shortcuts that cannot be reset??

    Again, thanks for the insights and well-done article

    • Uh, seems strange, Steven… To my knowledge there is no pre-defined shortcut for a Red flag in Mail. And I’m also pretty sure there is not a single menu command that uses Opt-Cmd-R as a shortcut, by default.
      My advice is to:
      – make sure you have correctly added the shortcut for Red, in the OS X Keyboard preference pane, *only for the Mail application* and not as a system wide shortcut
      – have a quick glance at all menus in Mail to find another menu command that has the Opt-Cmd-R already set (look at the right of the name of the command in each menu: if the command has a keyboard shortcut, it will be displayed next to its name); by default, you should have none; if you see one, get back to the Keyboard preference pane and delete the shortcut for that other menu command, and you should now have Opt-Cmd-R work correctly.

      I guess there are system wide shortcuts that can’t be changed, but again, Opt-Cmd-R should work if set *only* for Mail.app

      Hope this helps.

  • I use Apple’s Mail and generally like it as you do. However, there are two quirky bugs in Mail that waste a lot of time and drive me nuts. Maybe you know a solution?

    1. You cannot copy, drag & drop text from the body of text in an email to the SUBJECT line.

    2. The basic copy, drag & drop function when applied to text in the body of an email works only some of the time. Most of the time, it duplicates what you have copied instead of moving it which then requires going back, re-highlighting the original text and deleting it.

    Any thoughts?

    • I’ve just tested it again on Mountain Lion (10.8.2 build 12C60) and, while I can’t drag & drop text from the body to the subject line, a classical Cmd-C then Cmd-V works for me.

    • Also, I have no problem dragging and dropping text written in the body of a message to anywhere else, it moves the selected text as expected.
      If we’re running the same OS X build, are you sure you haven’t installed any third-party mail app/plugin that could cause this bug? If you have any plugin, try disabling it and see if it solves your problem.

  • After the purchase of a new MacBookAir I want to give Mail.app a chance > and this for the simple reason of solving, once and for all, the synchronization issues with my Iphone. How painful! I was used to Entourage, and must say, what a setback..!
    Main issues: 1) Size of font when composing it! I almost need glasses– how comes the typeface is so small? 2) Mailboxes: I use several accounts: what a mess: some create a file system for their own, some don’t, and I can’t figure out why. In Entourage, all accounts created their own file system (inbox/outbox/sent etc) on top of the general Inbox. Easy! 3) Have you tried attachments with mail? Sometimes they appear as attachments, sometimes they are integrated in the email.. I takes 2 or 3 manipulations to actually locate and open an attached PDF… This point has NEVER been an issue with.. Entourage.. .. Everything seems so ..unstable.. with Mail and I am extremely surprised that we are even discussing about this. Isnt Mac able to deliver anything better than THIS? I like your idea of using smartboxes.. but it’s the basics that need to be fixed first. User Experience they call it…. I would like to read from you here..

    • Hi Fresco and thank you for your comment.
      I can understand your frustration as every email client has its own interface. I’ve never used Entourage. It actually came with my Office for Mac 2008 install disk but I’ve never wanted to give it a try because I’m happy with Mail.app.
      However, i can see a solution/tip to offer you for each of your problems.

      1) About the font size:
      Go to Preferences > Fonts & Colors > Message font > Select… This will change the size of the font in incoming messages as well as when you compose a new one

      2) About mailboxes:
      In my system, I never care which mailbox the message comes from, in fact.
      I have two personal addresses (one from Gmail, the other from iCloud) and one professional. I don’t look at professional mail at home and don’t look at personal email at work. That means that when I’m at home I deal only with personal things and it doesn’t matter to me what address I use to reply, given that by default Mail.app uses the address the sender wrote you.
      About the fact the each email provider creates a system on their own, I know this might be a problem… except that I don’t even care of traditional mailboxes (i.e. Inbox, sent, priority, spam, etc.), I only use my Smart Mailboxes, and yes I’ve created one for Trash, one for Sent messages, so I never have to look at the Mailboxes list, that’s why I even hide the list ;-)

      3) About attachments:-
      Usually, pictures and sometimes PDF are displayed inline when you receive a message. I find that so much more easier to deal with: I don’t even need to first download the file to see what it is. That means that if I don’t need the file, I won’t even clutter my hard drive in the first place because I won’t even have to download it. I can even have a full screen Quick Look at it without, again, even having to download and open the file.
      To open an attached PDF, just double-click on its icon and it will be opened. If instead you click the Save button in the email, at the bottom right in the head of the message, it will be saved in the default folder you defined in Preferences > General > “Download folder”.
      Next to this “Save” button you will also find the “Quick Look” button I wrote about above.
      If you don’t see these buttons, that’s probably because you’ve hidden it: click on the blue “Details” word just below the date/time, at the right in the head of the message.

      Hope this helps.

  • Great idea, but when I set up Unread emails, it contains 5,000+ emails that mail downloaded when I set up my account. For some reason it downloaded every email I have ever gotten or sent into my inbox. I use Gmail, and when I log into it on the internet (not using mail app), my inbox is cleaned up. Is this an OS X mail glitch or on purpose?

    • I think what is happening for you is that you have to go back into your Gmail account under SETTINGS and then IMAP and uncheck “All Mail”. This is a common challenge when using Gmail account in Mail.app

      Apple’s email client will count the copy in your INBOX and the copy in the ALL MAIL folder on Google’s servers as two copies of the email. By telling Google not to map ALL MAIL to your IMAP client, these emails should go away and you will properly reflect your INBOX as it shows on Google.

  • The only thing I could add to this incredible thread is to check out “True Preview”. It can be found here: http://christianserving.org/category/project-release-compatibility/mac-os-x-10-8-mountain-lion

    The caveat is that this is truly a work in progress and many older features are no longer supported in Mountain Lion. However, what it does do is allow a true PREVIEW window in the Mail.app

    Apple has always said they do not have a “preview” window like Outlook. When you click on an email in Mail.app, its automatically tagged as “read”. What this plug in does is allow you to set a timer on just how fast Mail.app changes the status from UNREAD to READ. I find this invaluable in my workflow as I can skim emails and ones that I want to keep for later (UNREAD) will stay tagged unless I either linger long enough OR tag them myself with .

    Then my Smart Mailbox labeled UNREAD keeps all the email I need a closer look at.

    Just a little something extra for the task of keeping an empty INBOX.

    • Thank you very much, Charles!
      I didn’t know about this one. Being able to set a timer for the switch from Unread to Read is one thing I was missing from my early days with Thunderbird. Great advice!

  • This whole workflow is brilliant in so many ways, i’m going to adapt a version of it for my own mail client.

    The big bummer about it, however, is that you can’t get true Gmail hotkeys.

    using “j” and “k” to navigate emails, open them quickly, hit “r” to reply, and then “send & archive” is soooo nice. with Mail you have to stumble through a bunch of pre-made an un-changeable hotkeys to try and make this happen. Ultimately because of this I have to stick with either the web Gmail client or Sparrow (and Sparrow is laggy as all hell…)

    • Thanks for giving us your opinion, T W. Indeed, it’s a bit sad that Mail.app is not a bit more customizable. Gmail keyboard shortcuts are super useful, indeed!
      You can modify some of the shortcuts of Mail.app, though, as long as they have a dedicated menu command (thinking about reply, compose, etc.) Just go to the OS X System Preferences > Keyboard and in the Keyboard tab, define which shortcuts you’d like to use, the way I described it in my article when defining a shortcut for color flags. But… the problem with OS X shortcuts is that you’re forced to use at least one modifier key (Cmd, Opt/Alt, Ctrl) before a letter for a shortcut to work.
      Thus, you’re right in that you can’t simply set R as a shortcut for reply, it should at least be Cmd-R or Ctrl-R or Opt/Alt-R.
      I’m afraid it won’t change any time soon as this is deeply buried into some OS X working “rules”.
      In that way, you’re right, the Gmail/Sparrow UI is superior.

  • Thanks for giving us your opinion, T W. Indeed, it’s a bit sad that Mail.app is not a bit more customizable. Gmail keyboard shortcuts are super useful, indeed!

    You can modify some of the shortcuts of Mail.app, though, as long as they have a dedicated menu command (thinking about reply, compose, etc.) Just go to the OS X System Preferences > Keyboard and in the Keyboard tab, define which shortcuts you’d like to use, the way I described it in my article when defining a shortcut for color flags. But… the problem with OS X shortcuts is that you’re forced to use at least one modifier key (Cmd, Opt/Alt, Ctrl) before a letter for a shortcut to work.
    Thus, you’re right in that you can’t simply set R as a shortcut for reply, it should at least be Cmd-R or Ctrl-R or Opt/Alt-R.
    I’m afraid it won’t change any time soon as this is deeply buried into some OS X working “rules”.
    In that way, you’re right, the Gmail/Sparrow UI is superior.

  • My workflow basically works like this. All emails go into my inbox and will stay there until it has been actioned/resolved/expired or whatever. So my inbox is essentially my todo list.

    I then have a mailbox setup where I archive the email. I have this mailbox in my shortcut area (or whatever it’s called) so I just drag the email there. I have quite a few emails I manage and have an archive mailbox for each one and this system works pretty well.

    I then have different mailboxes within my archive folders for different clients, emails from my accountant, sales, customer emails etc. But using my method I have to manually sort those emails once I have archived them.

    I was hoping I could setup a rule that when I move the email to my archive folder I could then trigger the rule to sort those emails into certain folders. It seems the rules are only applied when the email is received.

    • Thank you for sharing your workflow, Mike!
      About the moment when rules are applied, here’s a little tip: when you’ve just created a new rule, Mail.app asks you “Do you want to apply your rules to messages in selected mailboxes?”. If you choose “Apply”, the rules will be applied to all emails that already are in your inboxes ;-)
      Then, indeed, this new rule will be applied only to incoming emails.
      Hope this helps.

  • Full screen mail? Yuck! Imagine trying to read a newspaper if the text was not in columns and you had to read a 100 words on one line.

    Personally, I don’t have my reader width greater than it would be if it were an A4 sheet of paper. I probably have it 8″ wide.

    • Your mileage may vary, of course, Brett ;-)
      You can still use my workflow without having Mail.app fullscreen.
      I have an early-2007 iMac with ‘only’ a 19″ screen at 1680×1050 pixels max., that’s probably why having Mail.app full screen does not bother me.

  • I’m trying to adapt your workflow – it sounds fantastic.

    However I’m running into a behavior that doesn’t seem to have been previously addressed in the comments: I set up my “Unread” smart mailbox just as you described, and it is perfect at collecting unread messages. However, once I’ve read a message and moved on to the next one, the read message doesn’t automatically disappear; I have to move to another mailbox and come back to Unread for it to clear.

    This is less satisfying (I don’t get to see my “inbox” getting to zero), and also removes the urgency that would counteract the temptation (very strong for me) to say “let’s wait to decide on this message until I’ve read some of the others in my list…”

    Any suggestions? My copies of Mountain Lion and Mail.app are up to date, and as far as I know I’m not running any plugins.

    • Having the same issue, hope we get a solution!

      God bless

    • Hi Bruce an Thomas, and sorry for my late reply, got some health issues these latest weeks.

      Unfortunately, this is one of the drawbacks of Mail.app: Smart Inboxes are not instantly refreshed. This is a “bug” (or is it a feature?) of Mail.app.

      However, since I regularly switch between my Unread, Need Action and Need Reply inboxes, it’s not much of a problem for me, regarding your ““let’s wait to decide on this message” temptation. Deciding on acting on a message has really come a habit for me now ;)

  • I love this article and have applied many of these ideas to my own mail. The one thing I was wondering is how you handle mail when you use another device other than your computer, such as an iPhone? The iPhone doesn’t give you the options of all the different flag colors.

    • Thanks Bernardo and sorry for my late reply, got some health issues these latest weeks.

      Like you, I’m not satisfied with Mail on iOS so far.

      Reader Stefan found a solution earlier in the comments thread. I copy and paste it below:

      > I often read e-mails on the go on my iOS-device and then often forget about them, as I didn’t highlight them.
      This is how I am tweaking around this:
      iOS is able to flag a message, but only ever highlights it as “red flag”.
      So I set up a smart mailbox that filters for red flags and named the mailbox “Review”. Once home, I open the “review” mailbox and sort the mails it into the correct category (e.g. ToDo, follow-up, reply).
      This is pretty much the system you described above, only that I don’t have to forward to a separate e-mail account. Obviously, I have assigned other flag-colours to my other smart mailboxes, as “red” is now reserved for “review”.

  • Wonderful article! Thanks for all of the great info! Can I ask you a question?

    What would you do in this case:

    Let’s say I’ve got a clean ‘Unread’ inbox that’s been emptied and all of my messages dispersed, then I get a new email from someone that does NOT require a follow-up, reply later, etc… all they need is a simple reply and therefore I reply. The message disappears.


    What if I don’t hear back from them and NEED to eventually follow-up (maybe with a reminder to reply)? If they aren’t in my ‘Unread’ inbox anymore, I am afraid I’ll forget about them! It’s a catch-22, but what are your thoughts?


    • I think you could flag it as “follow up” before hitting reply. Of course, you will still need to monitor your follow up mailbox periodically.

      • This is exactly what I’d do, thanks Bruce, and thanks for your question, Thomas.

  • Great article and really can put this to good use. My one challenge is much of my email management is done on my iPhone (in the native mail app). Is there a way people have implemented smart mailboxes and make it work with iPhone mail?

    • Thanks for your feedback, Paul.
      Unfortunately, like you and many others, I’m disappointed by Mail on iOS so far.
      Here’s a satisfying solution reader Stefan found earlier in the comments thread :

      > I often read e-mails on the go on my iOS-device and then often forget about them, as I didn’t highlight them.
      This is how I am tweaking around this:
      iOS is able to flag a message, but only ever highlights it as “red flag”.
      So I set up a smart mailbox that filters for red flags and named the mailbox “Review”. Once home, I open the “review” mailbox and sort the mails it into the correct category (e.g. ToDo, follow-up, reply).
      This is pretty much the system you described above, only that I don’t have to forward to a separate e-mail account. Obviously, I have assigned other flag-colours to my other smart mailboxes, as “red” is now reserved for “review”.

  • Fantastic article. Has turned the Mail.app into an extremely useful tool in my day to day work.

  • Great post on Mail, which I’ve been using for a couple of years. I especially like your ideas on the use of Smart Mailboxes. One fault I have in the most recent version of Mail is that I cannot embed a link in a banner that is part of a signature.

  • when i switched from windows to mac back in 2009, my first preference was Entourage, wasn’t satisfied with that, then after having outlook i was feeling comfortable as i was using that since long time, the reason, i was having POP3 emails and all data was saved on my Mac, then after OS X Lion, things started getting changed a i gave a try to Mail and converted all my email data from outlook to mail, I wanted to have all my folders and mails to be sync all across my iOS devices and Macs same way, then i read about IMAP and Google Apps, i switched my two companies email domain on Google Apps and turned on IMAP and on my 3 other gmail accounts, uploaded tons of my emails to google server and then sync all mailboxes with server mail boxes and then i enjoyed everything same on all my devices, i never looked to some other mail client since i started using Mail.app, its so powerful and goes very good with Google accounts, i must praise IMAP system and Google for this great service in real cheap price, the UI of Mail App is so clean and crisp which never let me try something else, I hate using web for email, for all those who never used Mail app, i recommend that you should at least give it a try i hope you will never regret, thanks for this great article, today i learned some good stuff about mail app.

  • Hello Pierre,
    I actually searched Google for ‘best ways to manage mail on mac’ and your page showed up. I am very inspired and am going to try and work exactly the way you do.

    Some quick questions though:
    1. Do you use POP or IMAP? Which one works better for you in Mail and why?
    2. If you do use an IMAP, like I do, I have multiple folders and rules setup on my online account. The rules don’t work half the time (for reasons unknown to me). Does Mail override these rules or work on it’s own. And then again, do you advise not to use these rules in the first place? If so, you recommend downloading all mail and sorting them based on how you defined it in your article.
    3. Lastly, do you also think that Sent Mail adds to unnecessary disk space? If I have conversation mode on, do I still need to have sent mail saved for mails that I send out.

    I look forward to your reply,

    Thanks again for a wonderful article.

    • Thanks for your feedback and questions, Akshat.

      1. I use IMAP.
      2. Which rules are you talking about? Those you can set on iCloud.com? Anyway, if you mainly read and sort emails with Mail.app, I’d recommend apply rules there, on the client side, not on server side.
      3. Plain text emails (and even HTML-based emails, provided they don’t have too much images within) really don’t waste a lot of disk space. Plain text is really lightweight, this is one of its many advantages ;) When conversation mode is turned on, sent messages will be grouped with the conversation they belong. So they might appear in both the ‘Sent’ and ‘Follow-up’ / ‘Need Reply’ / ‘Need Action’ Smart inboxes. But this does not add up disk space, as Smart Inboxes do not duplicate email messages.

  • Hi – I also really enjoy Mac Mail but after 23,000+emails (regardless of how they are sorted, grouped, tagged or managed) it is slowing down to the point of not being very effective.

    My email is through Gmail so for the time being I’m logging on directly to their webpage – but I don’t love it, far from it. I don’t want to delete anything but I can’t seem to figure out how to sort or hide things from being imported into Mail. I would willingly group things into folders if I thought I could prevent them from being imported/updated through Mail but it seems like all of the folders I have created through Gmail are imported to Mac Mail, and I don’t think the ‘archive’ function through Gmail does anything useful.

    Do you have any suggestions? Thanks very much in advance.

    • I must admit I don’t have to deal with such a large collection of email, since I delete lots of emails. Information I really need to keep (incl. conversations) is exported as individual plain text files from Mail.app into Notational Velocity, a plain-text notes taking app. It’s great for dealing with a lot of (as in “thousands of”) .txt files.

      I can see three starting points to fix your problem:
      – have you considered putting all your ‘old’ emails in an Inbox and archive them as an .mbox file that you will open at will? (in Mail.app, menu > Mailbox > Export Mailbox…)
      – MailSteward might be a solution to deal with huge email collections: http://www.mailsteward.com/
      – someone has the same problem here: http://www.hawkwings.net/2006/08/21/can-mailapp-cope-with-heavy-loads/ Maybe you will find a satisfying solution.

      Hope this helps.

  • Awesome, changed my life. Over 4000 unread to inbox zero in 2 hours.

    Thanks for sharing.

    • You’re welcome, Tim, glad to help you!

  • Hey,

    you should definitely have a look at DockStar. Works wonderfully with Smart Mailboxes and adds extra badges for them in the Mail.app icon.

    Btw, how are you dealing with the fact that if I flag a mail which is part of a conversation, the whole conversation gets flagged and the number of items is not increased by one but by the number of conversations one had?

    • Thank you for your suggestion and question, Johannes.

      Re DockStar, actually I chose *not to* display how many messages I have in my inboxes on the dock icon of Mail.app. I find that too distracting ;) Same for badges on iOS: I don’t like them and hide them whenever possible.

      Re flagging, if you select a given message in a conversation before applying a tag, this tag will be applied *only* to the selected message ;)

  • I pretty thorough little survey and a few things of interest in there that I’m not already using (I do prefer Mail to my Gmail or other readers I’ve tried). The one thing that’s really frustrating me is a two-fold problem with Flags:
    1. I really need 2-3 more flag colour options than I currently have. The limitation seems an odd choice and I understand the last third party app that could deliver that expansion was locked out after Snow Leopard.
    2. Once I’ve named my different coloured flags, I can’t re-order them to make more sense in terms of my own priorities. I’m stuck with the order the app puts them in as they’re created.
    Am I missing something on either of these points?

    • Jowi, thanks for your question.
      Re 1. I can’t help you for now, sorry…
      Re 2. Do you know you can rename flags? http://mattgemmell.com/2011/07/21/renaming-flags-in-mail-on-lion/ So, maybe if you rename them by prefixing the name with a number, like 1-flagA, 2-flagB, it would change their order? I haven’t tried it yet.
      By the way if you’re just talking about the order of Smart Inboxes placed in your favorites bar, you can just re-organize by simple drag’n’drop.

      Hope this helps.

  • Thanks for sharing this. I’m definitely more productive with emails when using my Mac.
    On a side note, I hope iOS comes out with an update for custom Smart Mailbox support soon so I can configure Mail the same way on my iPhone.

    • Same hope here, Puneet!
      Thanks for the feedback.

  • I have 4 Mac devices that I want to have updated at all times with flagged messages, read messages, and smart mailboxes etc. So if I read and flag an email on my iPhone, I want it to be read and flagged on my Macbook when I get back to my office. Then when I go home and go thru my mail at night using my iPad, I want this to be reflected on my MacbookAir when I travel the next day….do you get the picture? Is there any way this can be done in Mail? Thanks

    • If you use Gmail with the IMAP protocol or iCloud (that also uses IMAP) it should work exactly this way.

  • great article. One question: I use a signature but I don’t want it to appear when I reply or forward a message. I just want it when I compose a new email. I have tried making a rule but I couldnt find any option for it. any suggestion?

  • Thanks for the walkthrough. As a new Mac convert (from Linux), I am trying to get my workflow configured and learn some of the new tools/shortcuts.

    Would you be able to elaborate on how you created the Applescript, saved it, and made it into a service? I’m almost there, but there seems to be a few steps missing.

    Thanks again for your excellent post.

    • Thanks for your feedback and question, Jeremiah!

      I have two solutions for you, about converting an email into a new task in TaskPaper.
      The first solution is a complete tutorial of how to convert the AppleScript (found at http://www.hogbaysoftware.com/wiki/AddCurrentMailToTaskPaper) into a service.
      The second, that I now uses, is much simpler but requires a paid ($4,99) third-party app called Popclip (but this app does much more than our precise use case: have a look at http://pilotmoon.com/popclip/)

      ** Important consideration: For both solution 1 and 2, you should have the TaskPaper document where you want to add the new task already open, otherwise it won’t work **

      Solution 1 (MailToTaskPaper service)

      To convert the Applescript to a service, assuming you run Mountain Lion, do this:

      1. in Automator: File > New > choose Service in the dropdown window)
      2. In the window, select Actions, type “Run” in the “name” searchfield: this will help you find the “Run AppleScript” command
      3. Drag and drop the “Run AppleScript” action to the window part that reads “Drag actions or files here to build your workflow”.
      4. In the “Run Applescript window”, replace all the purple text with the text below:

      on run {input, parameters}

      — new script rewritten for automator
      tell application “Mail”
      set theSelection to the selection
      if the length of theSelection is less than 1 then error “One or more messages must be selected.”
      repeat with theMessage in theSelection
      set theSubject to subject of theMessage
      set theDate to date received of theMessage
      set theSender to sender of theMessage
      set messageURL to “message://%3C” & (message id of theMessage) & “%3E”
      tell application “TaskPaper”
      tell front document
      tell project named “Inbox”
      set newEntry to make new entry with properties {entry type:task type, text content:theSubject}
      tell newEntry
      make new entry with properties {entry type:note type, text content:”From ” & theSender & ” on ” & theDate}
      make new entry with properties {entry type:note type, text content:messageURL}
      end tell
      end tell
      end tell
      end tell
      end repeat
      end try
      tell application “Growl”
      set the allNotificationsList to ¬
      {“Mail to TaskPaper success”}
      set the enabledNotificationsList to ¬
      {“Mail to TaskPaper success”}
      register as application ¬
      “Mail to TaskPaper” all notifications allNotificationsList ¬
      default notifications enabledNotificationsList ¬
      icon of application “TaskPaper”
      notify with name ¬
      “Mail to TaskPaper success” title ¬
      “Added to TaskPaper” description ¬
      theSubject application name “Mail to TaskPaper”
      end tell
      end tell

      return input
      end run

      5. At the top of the ‘workflow’, choose “Service receives” > “no input” in “application” > Mail

      you should see something like this: http://cl.ly/image/2P01021Q3k3k

      6. Save your Automator document in your /[user home]/Library/Services/ folder by giving it a name like “MailToTaskPaper”

      [user home] is the name/path of your “home” folder, the root of all your documents and subfolders. For instance, I’ve created a user ‘pwizla’ so my home folder is /pwizla and is located at path Macintosh HD/Users/pwizla

      If you don’t have a Services folder in your Library, create it and name it exactly like this: “Services” without the quotes of course.

      Your [user home]/Library folder might be hidden. To reveal it in the Finder, open a Finder window and either type the complete path /Users/[user home]/Library in the “Go to the folder” text field (that appears after pressing Shift-Command-G) or hold down the Opt (or Alt) key while showing the content of the Go menu in the menubar and select Library.

      6. Once you’ve saved your service, quit and relaunch Mail.app and the newly created service should appear in the menu bar under Mail > Services..

      Solution 2: Using PopClip and its TaskPaper extension

      1. Buy, download and install PopClip
      2. Add the TaskPaper extension for PopClip, found at http://pilotmoon.com/popclip/extensions/
      3. Select some text in the email (either its subject or content) and in the PopClip window that appears, launch the TaskPaper command, and you’re done!

      see: http://cl.ly/image/0O471u0B3r0q

      • Forgot to mention that, when using solution 2 (PopClip), if the selected text does is not preceded by a dash followed by a space, PopClip will copy the text to TaskPaper but as a note.
        Don’t forget, within TaskPaper, to prepend the text with a dash followed by a space to have TaskPaper recognize it as a note.

        That’s why, when on the go, I email myself a task, I put the text of the task in the subject line and prepend it with a dash and a space.

        For instance, I email to myself a message that has an empty body but a subject line that reads “- pay the gas bill” (without the quotes), and when I select the subject line and uses the TaskPaper PopClip extension, the copied text is instanly recognized as a task ;-)

        • (**typos in the previous comment, read this one instead**)
          Forgot to mention that, when using solution 2 (PopClip), if the selected text is not preceded by a dash followed by a space, PopClip will copy the text to TaskPaper but as a *note*, not as task.
          Don’t forget, then, within TaskPaper, to prepend the text with a dash followed by a space to have TaskPaper recognize it as a task.

          That’s why, when on the go I email myself a task, I put the entire text of the task in the subject line and prepend it with a dash and a space.
          For instance, I email to myself a message that has an empty body but a subject line that reads “- pay the gas bill” (without the quotes), and when I select the subject line and uses the TaskPaper PopClip extension, the copied text is instanly recognized as a task ;-)

  • I’m finding that ‘Move to Trash’ does not seem to work in the Rules. I have set up a rule that looks for all mails with a certain domain name. It is instructed to ‘Mark them as Read’ and ‘Move to the Trash’. It only applies the former.

    • I had the same issue, Sean.
      For whatever reason, it works if you permute the actions order:
      Delete message first then mark it as read.


      It works this way for me.

  • Hey, thanks for this very comprehensive guide. What I don’t understand though is, why would anybody create smart mailboxes for Sent and Trash? I’m using the mail.app with three email accounts and I can simply drag the parent Sent and and parent Trash folders into the favorite bar to get a summarized folder for all my accounts. Is there any difference, advantage or disadvantage compared to creating a smart mailbox for Sent and Trash vs using the default parent folders?

    Thanks in advance

    • Thanks for your feedback and question, Travis.
      Indeed, maybe was it not clear enough in my article, but I don’t create any Smart Inbox for Sent and Trash, I simply drag the corresponding folders to the favorites bar.

  • How do I make a smart mailbox that only just shows up unflagged messages

    • Ah never mind, I figured it out. LOL


      So simple.

      This is the only thing i do differently from what you mentioned above. I use unflagged messages smart mailbox rather than an unread smart mailbox.

      Because I find that unread smart mailbox doesn’t have all my emails in my inbox that still need to be processed in case I clicked on to read it but didn’t do anything with it.

      • Nice suggestion, Trey, thank you!

  • Much of this has to do with organization, and I do all my organization in Evernote, after simply exporting into Evernote any e-mails that need further action, and then archiving all of the e-mails immediately. But thanks for the tip of keyboard shortcuts, I didn’t know about that one!

    Another thing that must be mentioned is to set the proper “IMAP prefix” in your settings (“[Gmail]” for GMail), and then using the menu option “Use this mailbox for…” to get rid of any IMAP folders from the sidebar, and to keep it all organized properly on the mail server. This really makes Mail.app look a whole lot cleaner, and makes all the features, such as archiving, work well.

    To do so, read this nice and easy walk-through for a quick first down:

    And check out this article if you really want to go for the touchdown:

    Thanks for the article, good stuff!

    • Thanks for the precisions, Daniel!

  • Thanks for this very clear and helpful tutorial. I’ll be following up on your Smart mailbox for coloured and flagged messages.

    I use MailHub for its close integration with Reminders. It enables me to schedule responses to task-related messages with precision, along with Notifications that enable me to forget about them in the meantime. I don’t like the Reminders UI (with its inability to change typeface and size), but the integration with Notifications is really valuable.

    • Thanks for your feedback, and also for bringing my attention to MailHub!

  • Hi,

    Excellent article. I’m ready to adopt many of the suggestions however, I collect around 50% of my mails from my iPhone, how do I allocate them quickly and easily whilst on the move.

    I looked at Mailbox for Iphone but will that conflict with your suggestions for Mail on Mac?