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.

  • http://burakerdem.me Burak Erdem

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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! ;-)

    • Jadin

      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! :)

      • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

        Thanks Jadin!

  • dixhuit

    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?

    • Jon Henshaw

      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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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 ;-)

    • Kultist

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


      • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

        Thanks, I didn’t know about this one!

    • Dominic Nemanja

      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.

      • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

        Same here!
        Thanks for your comment, Dominic.

  • Jon Henshaw

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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.

    • Charles Southey

      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.

      • Simon

        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.

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

          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 ;)

  • Steve Castaneda

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

  • Mavado

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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.

    • Greg

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

      • http://mavado.eu Mavado

        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!

  • Muratcan Simsek

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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.

  • Simon

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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…

      • Carles

        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.

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

          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.

        • http://danielkoskinen.com Daniel

          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?

  • Renee

    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?

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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

  • David

    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!

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

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

    • anotherPhil

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

      • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

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

  • jmbill

    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.

    • Phil

      Hasn’t Thunderbird development been discontinued?

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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 ;-)

  • Phil

    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?

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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!

      • Phil

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

        Do you have an article on nvAlt yet?

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

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

        • Phil

          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.

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

          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 ;-)

      • carles

        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.

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

          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 ;-)

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

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

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

          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.

      • Jim

        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.

        • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

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

  • Reid Leamaster

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

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

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

  • Greg

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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!

  • Jeremy

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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!

  • Mark

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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!

  • http://thatryan.com Ryan

    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!

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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.

  • Martin

    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


    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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.

  • Henk Keuris

    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.

    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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 ;-)

  • http://palobo.tumblr.com Pedro Lobo

    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!


    • http://mac.appstorm.net/author/pwizla/ Pierre Wizla

      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