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Apple Mail: The Yosemite Progress Report

by Joe Kissell

About a year ago, following the release of OS X 10.9 Mavericks, I wrote a little article expressing unhappiness with some of the changes to Apple Mail — especially for Gmail users (see “Mail in Mavericks Changes the Gmail Equation [1],” 22 October 2013). That rant turned into a bit of a meme, enough so that I was immortalized as a green rage monster [2]. Over the following few months, Apple addressed many of my concerns in a series of updates (see “Mail in Mavericks: Is It Safe Yet? [3],” 11 November 2013, and “Mail Improvements in OS X 10.9.2,” 25 February 2014), and most of the furor over Mail’s period of spectacular misbehavior died down.

Now that 10.10 Yosemite has been available for a couple of months (and the 10.10.1 update has been out for a month), I wanted to revisit the status of Apple Mail. Is it safe to use yet (or again)? Did Apple fix (fill-in-your-favorite-bug-here)? Are the new features worth it? Has Apple finally given Mail the care and attention it has needed for so long?

The short version is that Mail is (for better and worse) about as reliable as it was in Mavericks. There are a few interesting new features, a few odd changes, and a few bugs. But for the most part, if Mail was working for you in later versions of Mavericks, you’ll have the same experience using Yosemite. If it wasn’t working for you in Mavericks, you’re not likely to find it substantially improved.

The Good News (with Qualifications) -- Let me start by saying that Mail continues to be my primary email client, and that I use it happily and successfully every day. As I write this, I’ve received 479 messages today, not counting spam. But my Inbox has only two messages in it. (That’s two more than I’d like, and I’ll deal with them after I’m finished with this article.) As an email power user, I find Mail to be an excellent tool for the job. (It did require a bit of customization, but I’ll get to that in a moment.)

However, note that I no longer use Gmail as my primary email provider. (To learn more about that decision, read my Macworld article “Why (and how) I’m saying goodbye to Gmail [5].”) Although I have many different email accounts that I use for testing purposes (including Gmail, Exchange, and iCloud), the account I rely on most heavily is a good old-fashioned IMAP account. In my experience, that’s the sort of account Mail works best with. When I hear tales of Mail woe, they most often come from people who use Gmail or Exchange, or who use POP instead of IMAP (see “FlippedBITS: Misconceptions about Changing Email Addresses,” 4 March 2014).

Furthermore, as I’ve often lamented, Mail’s default configuration is awful. In order to make Mail usable, I had to display and rearrange the mailbox list, create smart mailboxes, customize toolbars and message headers, fiddle with numerous preferences, and set up a bunch of sorting rules both on my mail server and within Mail. I also had to add several third-party plug-ins, of which the most important to me are Mail Act-On [7], SpamSieve [8], and GPGMail [9]. But the end result is a client that behaves almost exactly the way I want it to. I’ve tried lots of other Mac email clients, and despite their many virtues, none of them give me all the capabilities that my customized copy of Mail does.

In short, if you think about email approximately the way I do (see “It’s Not Email That’s Broken, It’s You [10],” 23 February 2013), you use a conventional IMAP provider, and you’re willing to spend a bit of time fiddling with settings and plug-ins, Mail in 10.10.1 is just fine. The further you find yourself from that position, the greater the chance Mail will annoy you.

Yosemite Changes -- Apart from adopting Yosemite’s new fonts and flat icons, Mail looks almost the same as it did in Mavericks. There are a few subtle changes. For example, section headings in the Mailbox List are no longer shown in all caps. If you receive a message that is both encrypted and signed, only the encryption badge appears in the message header, not the digital signature badge. And although the From pop-up menu still exists and still lets you choose a different address or account to send a message from, for some reason it doesn’t look like a pop-up menu until you hover over it. But these are all trivial things.

Of the more substantive changes, the three biggest are Mail Drop, a new feature that routes attachments via iCloud rather than enclosing them in the body of your message; Markup, which lets you annotate PDFs and graphics without leaving Mail; and Handoff, which enables you to start composing a message on one device and pick it up instantly on another (without even saving it as a draft). These features all work approximately as advertised, and they’re nice, but they all feel sort of tacked-on. I had been hoping the Mail team would take this opportunity to seriously rethink some of the less successful aspects of Mail’s user interface, fix long-standing bugs, and modernize Mail with new organizational and automation features. Alas, all these hopes will be rolled over to my OS X 10.11 wish list.

If you want to know whether Mail “finally” plays nice with Gmail or Exchange, all I can really say as the most casual user of both account types is that I don’t notice anything significantly different from the way Mail worked in Mavericks. That is, there are no fundamental design changes, but at least some of the bugs that existed in 10.9.5 still exist in 10.10.1.

There Will Be Bugs -- I could spend a whole article cataloging Mail bugs both large and small, but I’ll just hit the highlights.

As I peruse discussion boards for Mail in Yosemite, I notice quite a lot of people complaining about Exchange sync problems (see, for example, this Apple Support Communities thread [11]). I’ve also read numerous reports of crashes, although I haven’t experienced any problems myself. One interesting bug I have encountered is that if you send a message in Plain Text format that includes an attachment — and that attachment is sent using Mail Drop — then sometimes the link to the attachment is the only thing that shows up for recipients or in your Sent mailbox; the rest of the message is blank. (The workaround is to use Rich Text, at least for any message that includes large attachments. You can change the format of the current message with Format > Make Rich Text or Format > Make Plain Text, or change your default setting in Mail > Preferences > Composing > Message Format.)

Shortly after Yosemite was released, I began to notice that when I moved a message from my Inbox to another mailbox, Mail appeared to do the right thing, but later the message reappeared in my Inbox (while a copy remained in the other mailbox). This turned out to have been caused by a bug in a beta version of Mail Act-On I was testing, so I didn’t think anything of it. But Dan Frakes reports that he’s seeing previously filed messages pop back into his Inbox with one of his Gmail accounts (but not another of them), even without the Mail Act-On plug-in installed.

Perhaps the most interesting and widespread bug I’ve heard about involves a new checkbox, which is optimistically labeled “Automatically detect and maintain account settings” and is selected by default. Apple claims this setting, when enabled, lets Mail automatically figure out things like which port and authentication method to use, which might otherwise require trial and error to determine. Unfortunately, many users have found that Mail guesses wrong; with that box checked, Mail overrides manually entered correct values and causes connection failures.

The fix is to uncheck the box and fill in the right port and authentication settings manually, just as in previous versions of Mail. But you have to do this for each account — both incoming and outgoing. To fix incoming accounts, go to Mail > Preferences > Accounts > Account Name > Advanced and uncheck “Automatically detect and maintain account settings.” For outgoing accounts, go to Mail > Preferences > Accounts > Account Name > Account Information and choose Edit SMTP Server List from the Outgoing Mail Server (SMTP) pop-up menu. Select an account in the list at the top, click Advanced, and uncheck “Automatically detect and maintain account settings.” Repeat for each SMTP account.

Take Control of Apple Mail -- People are constantly asking me if I’ve tried this or that hot new email client that promises to revolutionize the whole concept of email and solve all my problems. And I say thanks, but my email is already entirely under control. Apple Mail is far from perfect, and I’d be the first person to point out its flaws. Even so, it’s the tool I like best, but that’s because I’ve spent years fine-tuning everything to my liking, figuring how to solve or work around bugs, and experimenting to figure out the most effective ways to use it.

If you, too, want to like Apple Mail but feel that you can’t quite get a grip on it, I’d like to offer my help. “Take Control of Apple Mail, Second Edition [12],” freshly updated to cover Mail in both Yosemite and iOS 8, helps you understand Mail’s idiosyncrasies, fix problems, optimize the app for greater efficiency, and even become a better correspondent. If you already have another email setup that works well for you, this book won’t try to convert you to a Mail user. But it will help you to get the most out of Mail and get a feel for how powerful it can be with a few tweaks.