Mail in OS X Yosemite: Explained

Apple's straightening out Mail problems with Yosemite, plus making it easier to attach big files

If there's one singularly weak spot in Mavericks, it's Apple's Mail app. It a mess, especially for Gmail users, and every Mavericks update has sought to fix it somehow. What's so incredibly frustrating is that Mail was, for the most part, solid in Mountain Lion. Mavericks Mail's many faults has left some users apoplectic, while others have gone to third-party mail clients in search of a better experience. Fortunately, Apple seems to have gotten the message, because Mail in OS X Yosemite is better.

Back to the fundamentals

Apple hasn't apologized for how much of a disaster Mail is in Mavericks, but the message was apparent at the WWDC 2014 keynote.

"...we really focused on the basics," said Apple SVP of software engineering Craig Federighi at the WWDC keynote. "Reliable syncing, fast switching between mailboxes, quick fetches of your new mail, the basics."

In other words, everything that Mavericks Mail managed to screw up. Thank goodness.

I'll reserve final judgment for the general release later this year, but I will say that Yosemite Mail is snappier than before and less prone to many of the problems I'm accustomed to in Mavericks, so on balance I'd say it's a welcome change.

Improved interface

Like other Apple applications in Yosemite, Mail has gotten a facelift to conform to the Yosemite look and feel. Typography is clearer, with translucency added to the Mailboxes sidebar.

There aren't any major changes to Mail's layout in this new release, just some enhancements here and there for clarity and simplicity. You'll now see a round profile image appear to the right of the sender's e-mail address. If no profile image is available, Mail displays their initials instead.


Yosemite Mail Markup

Mail has always made it easy to attach documents, but Apple's taking it one step further by introducing a new feature in Yosemite called Markup. Markup makes it possible to do exactly that — mark up the files you attach in mail.

What's more, Markup sports a magnifying loupe, so you can draw attention to a specific portion of the attached document by zooming in. You can also draw shapes like arrows, and circles, which Markup will automatically try to straighten and neaten up. You also have the ability to draw shapes and add text annotations, and fill out PDF file attachments, complete with signature.

Markup isn't doing anything that you can't do already with apps like Napkin or Skitch (opens in new tab), which may leave some concerned that Apple is once again pushing out third party developers with this new feature. But Napkin and Skitch are standalone apps that enable you to mark up images. Markup is embedded as a feature of Mail, which limits its overall utility as a markup tool.

Mail Drop

One of the biggest pain points with mail use is attaching files. Internet service providers and e-mail providers often put restrictions on the maximum size of file attachments to keep their servers from getting clogged up with pictures of people's kids and videos of graduation processions. Apple's doing something about that with a new OS X Yosemite Mail feature called Mail Drop.

Yosemite Mail Drop

Mail Drop shunts off the collection and retrieval of file attachments to iCloud, making it possible to attach much larger files than you ever could before — up to 5 GB at a whack.

As far as other Apple Mail users are concerned, it's business as usual: Apple's made the process transparent, so you'll still see the file enclosure attached just like you always have.

But if you're using a different Mail client, or if you're on a PC or another computer, you'll see the attachment as a text link. Clicking on it will then retrieve the file.

The bottom line

Even if Apple only makes good on the promise of improving Yosemite Mail's "fundamentals," they'll give plenty of reason for Mavericks users to celebrate. The new features like Markup and Mail Drop are certainly going to make many Mail users' lives easier, too.

Have you had problems with Mavericks Mail? Do you often attach big files to emails? What features in Yosemite Mail excite you? Let me know in the comments.

Peter Cohen
  • Any news on better compatibility with Gmail? We know the problem is basically Google´s use of a "less than standard" setup. Has Apple found a way to deal with that?
  • With a developer preview release it can be difficult to tell whether things are better or worse. What I can tell you at this point is that I'm not seeing Mail populate with new messages until I wake from sleep and my Mac is on for a few minutes. But I don't know if that's an issue with Power Nap, Wi-Fi or what. I'll wait for a few more builds before I start getting worried.
  • I just wish they rework all the interface. Including icon.
    just give me a small-n-simple look, like Sparrow. Apple've got it for iTunes.
  • You do realize that the main reason for why Mail was finicky and didn't always work with Gmail is because of non-standard / Custom way Google sets up Gmail, which at times is impossible to predict. It's funny that when these issues started arising, the media was blaming Apple for their "crummy" Mail application and no one looked to Google as a source of why there are comparability issues. Sent from the iMore App
  • You do realize that the main reason for why Mail was finicky and didn't always work with Gmail is because of non-standard / Custom way Google sets up Gmail, which at times is impossible to predict.
    There are two different things going on here: Google does indeed have a non-standard IMAP implementation in Gmail, which complicates things dramatically. But Apple did make changes in Mavericks Mail to treat Gmail differently than previous releases of Mail. So it's a complete shit show: Apple broke what it had done to accommodate Gmail, which was already "broken" to begin with. (Joe Kissell has an excellent piece over at TidBITS that documented early on what was going on. As Mavericks has evolved Apple has tried to smooth things out, but it's still rough going for some users.)
  • Any word on Mail Drop using iCloud Drive storage? Or it's own separate, time delayed storage? Sent from the iMore App
  • This is still something I'm trying to figure out.
  • Peter, did you finally figure it out? I'm still wondering.
  • Mail Drop will not use your available iCloud storage. Attach away!
  • I'd like to see better enterprise supportability. Right now if you work in an Exchange or EOL 365 world, you pretty much need Outlook 2011. I know Microsoft is coming out with a new version of Office for the Mac, but would love to not have to run it all the time. Maybe mail and calendar will get some of the functionality quickly demonstrated such as viewing users free/busy time when setting up meetings etc. Those little things that are required to work in a Microsoft corporate world.
  • Care to elaborate what exactly your problems are? We have far over 1,300 users accessing Exchange using Mavericks Mail and no problems whatsoever. There is also full support for viewing free/busy information in Calendar since many years, and it works flawlessly. Actually we were having a lot more problems with (Mac) Outlook than with Mail/Calendar. To the point that we removed Outlook from all Mac clients.
  • Sure I'll elaborate for the poster, Mail does not support Exchange Active Sync [EAS]. EAS is used for syncing e-mails as well as some other serivces. This is completely separate from Exchange. Therefore Exchange Server based e-mail servers, which your company would use does not use the EAS infrastructure that your Exchange Server implements. Herein lies the further issue, Office 2011 for Mac also does not support EAS. Therefore, you would have to use IMAP or POP still. The only useful way to use a desktop program to access you e-mail in OS X 10.9 and 10.10 so far is to load up a virtual machine with Windows OS and load Outlook from the Microsoft Office 2013 package. On OS X 10.10 [which I am on now] I am awaiting to see if Apple chooses to not alienate their EAS users anymore. So far I am disappointed; however, the situation is very fluid that may or may not change. As of right now there is no VMWare Fusion support for OS X 10.10 available to the public. I have an internal developer build of VMWare Fusion that runs on OS X 10.10; however, that is not currently available to the public. I have heard other virtualization packages may or may not be operational as OS X 10.10 builds may continue to break virtualization software capabilities. tl;dr version there is no EAS-Exchange support
  • I did not talk about EAS, our own Exchange servers have EWS enabled and all Mac clients work flawlessly without any need for VMs et al, including calendar support with free/busy views in Calendar's Availability Panel. Also works fine with hosted Exchange accounts. No idea about though.
  • I know you didn't talk about EAS, as I said the the OP you replied to did. When referring to the lack of EAS support as many others have in this chain and other posts.
  • "The only useful way to use a desktop program to access you e-mail in OS X 10.9 and 10.10 so far is to load up a virtual machine with Windows OS and load Outlook from the Microsoft Office 2013 package." There is e.g.
  • For security reasons this is not an acceptable solution.
  • I'll stay with Airmail for now unless I see some major improvements. It has been very solid for me for the last year and I have very few complaints.
  • Can an account be added from System Prefs the same way you can in iOS 7? That's my alternate email and it took some work to set up in the mail app. Still haven't managed to get the calendar set up though. Sent from the iMore App
  • Unfortunately not yet and there's no indication about whether or not such support will come.
  • I know it's doesn't exactly pertain to this, but this effort to improve OS X Mail (especially it's compatibility with Gmail) makes me hope they'll do the same with iOS Mail. It'd be nice to not have to rely on the Gmail app for my mail notifications -- especially since I still prefer the stock Mail app over any of the 3rd party alternatives (shocking to some, but true nonetheless).
  • Tables!!! Please... when?
  • Is the issues with mavericks finally fixed? Even after the last update it was hit or miss Sent from the iMore App
  • I'm sick of gmail sucking in so much so I'm looking for a better email client to work with my domain email. Rackspace seems reliable though expensive for a single user, Fastmail is another option. Anyone know of any others? Another question I had was regarding markup within the email when you send a marked up image to a none user does it arrive as a markup image? Do the changes get burnt onto the image? Sent from the iMore App
  • What's wrong with Mavericks mail? It's the still best default email client I've ever used. And man, the scrolling is just so smooth. Sent from the iMore App
  • Same here. Mail is my goto app. It works fine for what I need. I have no issues with my Gmail account. It’s these damn ‘power’ users always harping about one thing or another. Nothing ever satisfies them. Nothing.
  • No option for a tabbed mail interface?
  • I'm often having to find ways of splitting attachments or reducing the size (often losing the original clarity of images), so looking forward to the new feature in Yosemite. It will be interesting to see examples of the text link procedure that non Mac users will experience. Sent from the iMore App
  • I find it completely surprising that I am the only one raising this, I cannot fathom how Mail cannot by now already include a tagging mechanism. I do tech. support and receive way too many emails to consider folders a solution, or smart folders an acceptable workaround.
  • I'm using the Yosemite public beta but I can't get Mail to open. Whenever I try it asks if I want to "Reopen" the windows after the unexpected quit, then it quits regardless of whether I select reopen or not. Any ideas??
  • I am encouraged to hear that Apple recognizes the performance issues. As a contractor I attache to 3 different IMAP domains as well as my personal email and a couple of POP accounts I use for anonymity and spam control. Between Mail's performance and the MBA 2013 wifi SNAFU I have been testing a Surface Pro 3. Nice what they have planned, but how about a range of useful features like an email merge, delayed or scheduled sending and such. I travel about 140,000 miles so depend on email. Working in a browser client is out of the question as I can be days without web access- so I could really use some increased features. That said, given that my domain is at Google and 2 of the other IMAP accounts are also there, a treamlined interface and greater efficiency with Gmail would be a huge help. As a sole prac, it would be silly to look at hosted exchange- but that is where I am leaning right now.
  • I am having the exact same problem. I connect to four different IMAP accounts, one Gmail account. If I disable all the IMAP accounts, Mail works fine, but with the IMAP accounts active, it quits immediately upon launch. If I attempt this three of four times, I can get it to stay open. What this tells me is there is a problem in the initialization of the IMAP connections. Once I force it through all the IMAP opening (by launching four times) it stays open, but then when it checks for mail again (five or ten minutes later), it simply quits. I encourage you to report this directly to Apple through their feedback assistant, as I doubt they are following this board.
  • Have they sorted our fonts and attachments yet? I have never managed to take advantage of the nice integration with the rest of the OS due to the fact that Apple insists on using inline attachments and doesn't give consistent enough outbound mail font and styling when the recipient uses Outlook. For business reasons I can't be sending inconstant mails to clients.
  • Mail is not better after installing the Yosemite OS. Now I'm unable to do Group Messaging. Before I was able to drag and drop the group or choose TO: CC: BCC: but not anymore. This is a big hassle for those of us who send group emails on a daily basis. Hoping Apple fixes this ASAP. I've already notified them in their community logs. Maybe others have complained too.
  • Hey RuthMaria, i' have the same problem in the new Mail app. After it was very easy to send an email to you contacts with the Contacts Panel. But now, with de + symbol in the destination cell you have to select your contacts one-per-one. Anyone knows a solution?
  • Personally, I couldn't give two hoots about Gmail, which I know is selfish, but I use and I don't understand how this has dropped off the radar so badly. I do get that Hotmail was horrendous, but Outlook (.com) is much better, and as an experience is nicer to use now than Exchange OR Gmail. However, in OSX Mail we now have: - No native support for Outlook (.com)
    - No chance of syncing contacts
    - A fiddly workaround for syncing a read-only copy of calendar to the calendar app. The only way I can get a good solution for Outlook (.com) is to use iCloud for contacts and calendar, and Outlook (.com) IMAP for mail. This works well for OSX or iDevices, but as soon as I go to use webmail I then have no contacts or calendar because they're not hosted there anymore. Personally, I would love Apple to introduce support for custom domains on which would solve all my problems as I would migrate in an instant, but as for people complaining about Gmail support in OSX, you don't know how good you have it!
  • I hope this is all its rated up to be.
  • I am frustrated by the 'show' of attachments. I would like to be able to choose to place the attachments as icons with filenames at the top or bottom of my mail, rather than the mess of pictures and pdfs and icons shown now.....