Mac OS X Lion 10.7 Deep Dive: Mail

Mail has received perhaps the biggest update of any of the pre-installed applications in Lion, with a column-based layout, new search methods, improved conversation threads, updated icons, and better support for Exchange and Gmail.

Column-based Layout

Moving to a columnar layout has a surprising number of implications. You might not guess that it would take much work to move a list of messages from appearing above the message preview to the side, but a lot of Mail’s previous functionality was based on having that wide, spreadsheet-style list of messages. For example, with the switch to a stack of messages on the side they’ve had to add a sort drop down (previously handled by clicking the column headers in the spreadsheet-like view).

Mail Sort

With the old layout it was easy to add a column to the list view if you wanted to see, for example, the number of attachments. The new layout has a little less flexibility and looks a bit cramped with every option turned on.

Mail Everything Message

The new layout has also prompted a change to the search filters bar. In Snow Leopard and earlier, when you started searching a bar would appear above the messages list allowing you to restrict search to a specific mailbox. In the earlier developer previews this was moved to a spot above the new message list, but in the most recent developer preview it has been integrated with the new “Favorites” bar.

Mail Save Search

Search mailbox filters in developer preview 3.

Mail Search Bar DP4

Search mailbox filters in developer preview 4.

Speaking of the favorites bar, it’s a list of mailboxes that you can customize. The thinking is that you can hide the mailbox sidebar most of the time and just use the favorites bar. If you need the full mailbox list there is an icon on the far left of the favorites bar to show and hide it. Or, if you don’t want to use the favorites bar, you can hide it (but if you do a search it slides down so you can still filter by mailbox).

And if you don’t like any of this new stuff you can still get the classic, messages-on-top layout. If you stick with the new layout, however, you can customize the message list a good bit, selecting how many lines (from none to 5) of each message to preview and whether to show a picture of each sender (based on pictures in your address book).

Mail Viewing Preferences


As Phil Schiller demonstrated at the WWDC keynote, Lion has a new search method that’s used in Mail and the Finder. It provides an interface to the search functionality that was previously only available when creating a smart mailbox. When you start typing in the search field an autosuggest drop down will appear, offering various ways to apply that search term, i.e., find emails where it’s in the subject, or where an attachment matches it, or where it matches the sender, etc. It tries to be smart with its suggestions – for example, if you type “ash”, it won’t just offer to look for emails from “ash”, but will show names from your address book that match (“Ashley”).1

Mail Search Suggestions

If you select one of these suggestions then your search term will be replaced by what Schiller called a “token”, which work kind of like the blue oval around email addresses in mail. On the left side of the token is what you’re searching (“From”, “To”, “Subject”), and on the right is your search term. You can click on the left side to change what you’re searching, and you can double click to edit your search term. As Schiller demonstrated you can add multiple terms to create fairly complex searches directly from the search field. One quirk is that if you don’t select one of the suggestions and just hit enter after putting in a search term your term won’t get “tokenized”; it will work exactly like search worked in the past.

Mail Search Token Options

You can choose to save any of these searches, at which point you’ll get the smart mailbox dialog that you may be familiar with from earlier versions of Mail, which makes it clear that these search tokens are a new front end to functionality that already existed.

Mail Search Save Smart Mailbox

Conversations Threads

Conversation threads aren’t technically a new feature in Mail, it’s just that they were so poorly done previously that no one really knew they were there. Lion fixes that. The threading is smart and the presentation excellent. In previous versions of Mail the threading was based entirely on the subject line. Now, “Mail groups messages into conversations based on many factors, including the message headers, subject, sender, recipients, and date.” From what I’ve seen so far it works.

Mail Conversation Threading

In addition quoted content is hidden by default, presenting a clean conversation. For those that hate top posting you can choose whether the most recent messages are at the top or bottom.

One other piece that makes the conversation view work is inline actions. Hover over one of the messages in the conversation and icons fade in to delete, reply, reply all, or forward the email. In true Apple style each of these actions animates. Reply, for example, fades in a new email window and a copy of the message jumps from the conversation into the new email window.

Mail Inline Actions

Everything Else

Gmail integration has improved, with a dedicated “Archive” button available for the toolbar. Unlike Mail on the iPhone and iPad, however, Lion Mail doesn’t have a single button that switches between deleting and archiving depending on what mailbox you are in. Archive is available for any mailbox; if you click it on a non-Gmail mailbox, it will just create a new folder called “Archive” and move the message there.

Mail Toolbar Options

“Move” and “Copy” buttons have been added for quick filing of messages. This functionality was available in previous versions of Mail but was only accessible from the “Message” menu.

Mail Move and Copy

And last but certainly not least, we’ve finally been freed from the tyranny of the font inspector. Developer preview 4 revealed the addition of an optional formatting bar in the new message window. Hallelujah.

Mail Formatting Bar

1In the most recent developer preview, however, it’s still a little flaky. Hopefully that is addressed before release.


51 thoughts on “Mac OS X Lion 10.7 Deep Dive: Mail

  1. Can you revert back to the original view rather than columns? It’ll just be really cramped on my portrait orientated second screen.

  2. Is there a way to include your own replies in email threads, like gmail does in the browser? I find this very handy for context, and which is why I’m going to stick with browser based gmail.

    • There is, actually. I didn’t got into it in this (although I probably should have), but there is an option to “Show Related Messages”. You can have related messages always shown through a preference setting, or you can add the “Show Related Messages” button to the toolbar and invoke it selectively. Where threading only threads the emails within the current folder (inbox, archive, etc.), the related messages are pulled from all of your folders (including sent). This could be really annoying due to duplicate messages (for example, in Gmail all your inbox messages are also in the “All Mail” folder), but luckily it consolidates duplicates and adds a little notice of how many duplicates there are.

  3. I am always losing the compose window when doing screen shot capture, often hidden under the mail mail window. Can you compose mail in the main mail window?

    • Nope. Although, when using Mail in full-screen mode you get a kind of modal overlay to compose your message rather than an actual new window.

    • There is no option to reply after. From what I’ve seen of various email clients and forums, replying after is losing popularity.

    • There isn’t by default, but you can go into System Preferences, Keyboard and add a keyboard shortcut. Just select “Application Shortcuts” in the list on the left, click the plus button, and add your shortcut.

  4. How are you able to get the Archive button working on a gmail account? I have 3 gmail accounts, and each time I press Archive, it creates a new folder called “Archive” and puts the email there.

    • You are correct – no matter what kind of account, clicking the “Archive” button will move the message to an Archive folder if it already exists. If an Archive folder doesn’t exist, one will be created and the message will be moved there.

  5. Jacob, Is there a way to create a way to toggle (for example an icon on toolbar) between the classic and new ‘lion’ format of Mail without having to go to preferences/viewing/clicking ‘classic view’? Some functionalities (such as cleaning up Inbox)/searches are much easier to work with in the classic view and for those, it would be great to be able to quickly revert to Classic view

  6. I prefer to use the old column style, which I have set.

    But I now have a ‘Rich’ column which contains text starting with ‘<LibraryMessage: '.

    How can I get rid of that column.

  7. I liked having the reminders (to-do) available on the email page because email generates a lot of my to-dos. Now, one can only access reminders from the calendar, or am I missing something?

    • Mail has notes, Calendar has to-dos, and never the twain shall meet. I haven’t seen any way to access to-dos/reminders from Mail.

  8. Is there anyway to have an image pasted into my email show up as INLINE, rather than an attachment? Prior to Lion, I was using Postbox, which does this… but I can’t seem to find a setting for it in Mail.

    • I did some research into this and it looks like Postbox is doing a pretty unique thing for their inline images. They convert the images into data URIs so they can embed them directly in the email. Mail does not offer this feature.

  9. I like the threaded view except for one problem. When you’re looking at a threaded conversation, there’s no way to see the replied or forwarded status of messages in the thread that don’t have an entry in the message list on the left. Is there any way around this problem?

  10. Is there a way to set a group of filters for each mail account? I have some folders named same in each mail account e.g. “statement” for bank statement and I need the filters to file incoming statement mail to each account to the statement imap folder in each mail account so that it gets organized on the server too. Any workaround…..if no way to have a group of filters dedicated to each mail account?

    • There’s not explicit support of “groups”, but you can create your rules (found in preferences) to do this. For example, if you have a Gmail and a Comcast account, you could create a rule for Gmail that says “If account is Gmail and subject is “Bank Statement”, move to folder Gmail -> Statements”, and another rule that says “If account is Comcast and subject is “Bank Statement”, move to folder Comcast -> Statements”.

  11. I see you have brief headers in the screen shot about conversation threads (re: underwater basketball) and I haven’t figured out how to display that. I know I can display full headers which I don’t want. I have a group where there are multiple people with the first name of “jim” and it would be nice if each conversation pane had the email/subject/date at the top as your example shows.

    • You can configure what shows up in each message’s header by going to Mail Preferences and under the Viewing tab changing the “Show header detail” value. There are four options: None, Default, All, or Custom. You may have yours set to None because mine is set to default and shows the info you are looking for. Regardless you can go to Custom and have it show whatever you want.

  12. Hi Jacob,

    I’m really loathing the Lion threaded view and wonder if you’ve found a hack or a way to turn it off. I know that we can go back to a classic view, but I don’t like the preview pane below the mailbox. I’ve been using Hanley’s preview pane in 10.6 and it no longer works. The problem is that the threaded view is really unreliable and buries messages in there that I don’t easily see. It also doesn’t clearly indicate whether I’ve replied to them without open each thread. Ugh! I sent my email newsletter out and it’s been a nightmare sorting through the replies. Any help?



    • No need to hack – you can turn off the threaded view by going to View -> Organize by Conversation in the menu. You can also customize the toolbar (right click in the toolbar area and select “Customize Toolbar”) with a Conversation toggle button.

  13. It doesn’t always work. I won’t group based only on subject. If someone sends me a message with the subject “foo” and I reply from a different computer/mail account, and they reply to that, it does not see the “re:foo” from them as part of the first “foo message.”

  14. When I drag a conversation with “Show related messages” on from my inbox into a mailbox for filing, the messages in my Sent folder don’t go. Do you know if there’s any way to change this behavior?

  15. I like the WideMail layout, but I want to have subject as a separate column (so basically a single row per e-mail as opposed to person from and then subject for each one. It’s the way it used to be with plugins like WideMail and others.

    I can add MORE by including the preview – not what I want. I also don’t want to go back to the “old view” because I want the preview to the right.

    Any way to do this?

  16. I do not like the way Lion Mail creates several duplicates of everything I type. I like Versions for Pages, but for email, it seems like a waste of space to save emails several times while I am composing them. Is there a way to remove these duplicate messages? I tried a script from Jolly Roger, but it does not seem to work.

  17. Does anyone know if there is a keyboard shortcut to un-flag an item? I grew used to flagging an item and then unflagging by pressing the same button, now it is more complicated and takes more time to do that, so maybe there is a keyboard shortcut…

  18. I’ve noticed that the icon that shows a message has been replied to (the little arrow) is no longer visible in the left-side column – is there any way to get this back?

    • mail has been great until we replaced a damaged macbook pro with a new one running mountain lion. The lack of the “replied” icon is a major frustration. How do we get it back. Has anyone seen a useful response to this issue?

  19. Any idea how to build Groups. I have no + like I did before at the bottom of my Group column. When I want to send to a group as I did i the past I have to go through my 395 contacts one at a time. Ideas Anyone?

  20. I have a GMail account. I am using my Lion Mail as my mail program instead of the browser from google.
    I also have a 2:nd email address which is linked to my GMail.
    When I am in the browser at GMail, I can reply on emails on my 2:nd email and I send it with the correct “from” address.
    However I do not know how to do that with my Mail program. Everytime I answer on emails over my Mail program, it always uses my googlemail as “from”.
    Can I somehow fix this so that I can answer with the “From” for my 2:nd email address using my Lion Mail program??!?!?! Please help, I am in need. Thanks

  21. When I do a “Reply” or “Reply All”, Mail seems to get rid of the original recipients in the body of the email. In other words, if there are 10 people on copy in the email and I selectively only reply to 4, I can never find out who the original recipients were. How can I stop this?

  22. Hi Jacob
    Is there a way to edit the subject line of an email that has been received in Mail? Sometimes a subject line of an email is not truly descriptive of the content, and it it useful to change it to something relevant (for example, when someone replies to an old message about a different topic instead of sending a new email about a new subject; or a fax to email program which simply has a subject of Fax Received, rather than the actual fax content). In Snow Leopard, the only way I knew to do this was from a tip I picked up: to drag the email to Desktop, open it in Text Edit (using Open With) and then manually locate the subject line and edit it, Save & close, then re-open using Mail, then from the Mail menu select Message, Move To, Inbox. I would then have a copy of the email back in my Inbox with an appropriate subject line, and delete the old version. I have tried this since moving to Lion, but cannot seem to get it to work. I go through the whole process, but there is no sign of the edited email afterwards.
    Any help on this would be much appreciated.

  23. Thanks for the helpful hints. I have two questions:

    I began setting up my mailboxes as “smart” ones and then realized that was significantly different than setting “rules”. I can’t move mail into the smart mailboxes, for one thing. Plus it copies to the smart box, rather than moving, so my inbox was still cluttered. I don’t see why anyone would use the smart box feature instead of setting rules — can anyone explain that to me?

    The other problem is that for some of my mailboxes, the “show related messages” drop-down in the view tab is not active, while in other mailboxes it is. In all boxes I’m able to “organize by conversation”, but I like the related messages option to capture the sent email also. Is this happening to other people?

    • I think your confusion lies with a misunderstanding of what a smart mailbox is. You should think of a smart mailbox as a saved search. It’s not an actual mailbox, and nothing is actually contained within it. It’s just a quick way to filter your emails based on some predefined parameters. As such it serves a very different purpose from rules.

      If you want an example of how one might use these, I personally have a rule that moves notification emails into a special “Notifications” mailbox. I use a rule for that because I don’t want to see those emails in my main inbox, so I want to actually move them. On the other hand, I have a smart mailbox that is for unread emails. The smart mailbox allows me to quickly see all my unread emails, across all my email accounts. I don’t want to move these emails from where they are, so I don’t want a rule. I just want to be able to see them listed together.

      Hopefully that helps. Per your other question I don’t know why the “Show Related Messages” button is disabled at times, so I’m afraid I can’t provide any insight there.

  24. Hi Jacob,

    I have a Gmail account where I am using Mail to access it via IMAP. I like to organize my mail items in folders. For example, under my Sent Mailbox, I created two folders (or Mailbox); Personal and Work.
    I would then move every sent items, either manually or via rules, to each corresponding folders.

    The problem is, the folders (or Mailbox) on the middle column always shows the ‘From’ field, which is my own name. I would like to see the ‘To’ field instead, so I can easily find the mail item based on to whom the mail was sent to. Is there a way to change the view of the mailbox?


    • I’m not exactly sure what you’re referencing but I’ll see if I have an answer. It sounds like you are using the “Classic” layout still. If that’s the case you can change what columns are shown in the list. You can do this by either going to View -> Message Attributes from the menu bar, or by right clicking any of the column headers in the list. If you are using the new layout, then this shouldn’t be an issue, as it defaults to showing the “To” field when you are looking at sent messages.

  25. Jacob,
    I have the same problem as mufti. The classic lay-out gives me the opportunity to select ‘from’ or ‘to’ (or any other possibility). However wit Lion all the subfolders (in the folder Send) show the ‘from’ field (in bold) which is indeed naturally me. Using the ‘sort’ feature doesn’t help. It still keeps showing the name of the sender. Rebuilding the folder doesn’t help either.

  26. Jacob,
    Thanks for your insightful comments. I’m hoping you can help me with a frustrating bug in my imail. I just installed Lion and set up my gmail IMAP accounts. My problem is with the new message display format. When I use the new 3 column format, my “Sent” messages all display the “From” rather than the “To” field. Since messages in the Sent mailbox are all from me, that’s not helpful. I want to be able to see who the message is sent To. I’ve tried every setting but for the time being will have to go back to the classic column layout. Any thoughts on fixing this would be greatly appreciated.

  27. Is there a way to prevent mail from “hiding” the file structure at the left side of mail when viewed in the “Classic”. I would greatly prefer it be “unhid” at all times, especially when I first open the mail program

  28. My biggest problem with Apple Mail (and most mail clients out there) is that there’s no easy way to get from a message in my INBOX to its entire conversation, which is always archived in my “All Mail” folder. One of the most common things I need to do is just to see the message to which something in my INBOX is a reply. Is there a hidden answer for this in Lion mail?

  29. I’m in agreement with Mufti and Moos – Im finding it incredibly frustrating that in the preview panel of any sent sub folders that I create, my name appears as the ‘from’ option when I would like it to show who the email was to! Of course I know it was from me! So hard to find emails to certain clients without switching back and forth to classic view!

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