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Apple Mail: The Yosemite Progress Report

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,” 22 October 2013). That rant turned into a bit of a meme, enough so that I was immortalized as a green rage monster. Over the following few months, Apple addressed many of my concerns in a series of updates (see “Mail in Mavericks: Is It Safe Yet?,” 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.”) 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, SpamSieve, and GPGMail. 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,” 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). 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,” 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.

Check out the Take Control ebooks that expand on the topic in this article:

Sure, you use Apple Mail, but are you using it effectively? Join email expert Joe Kissell to find out what's new with Mail in El Capitan and iOS 9, and how to best set up your Gmail, iCloud, IMAP, and Exchange accounts. Joe helps you take Mail to the next level with plug-ins and automation, shares his award-winning email management strategy, explains how to customize Mail, and solves common problems.


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Comments about Apple Mail: The Yosemite Progress Report
(Comments are closed.)

James Reynolds  2014-12-19 12:14
“Automatically detect and maintain account settings” also crashes the auth process of dovecot on OS X Server.
Joe Kissell  An apple icon for a TidBITS Staffer 2014-12-19 12:46
Lovely. As I just told someone by email, this new checkbox is yet another indication that Mail does not receive adequate real-world testing. When a problem is this widespread, something must be seriously wrong with Mail's QA process.
Walter Underwood  2014-12-19 13:48
I use with the Microsoft-hosted Exchange. There is no way that Apple can adequately test this, because it works differently day-to-day. It will fail one way for a while, Microsoft will refuse to accept the bugs from Mac users, then it will work correctly again. Zero changes to, configs, or Mac OS.

The problem is in Microsoft testing, not Apple testing.
Alan Forkosh  An apple icon for a TidBITS Supporter 2014-12-19 16:04
In Mavericks, if you 'right-clicked' on a link in a message, the 'Open link behind mail' command in the menu sometimes worked and sometimes did not.

In Yosemite, any attempt to open a link from the menu (either immediately or behind) fails. The problem has existed since the first beta and has been reported via the feedback mechanism. It also is the subject of two threads in Apple discussions: and

Note that one can open the link behind mail by command-clicking on the link, but that requires w-hands rather than the one-handed operation that would be required if the secondary menu command actually worked.

Given that the bug is unambiguous and relatively easy to test, I have hopes that it will be fixed.
Judith Battershill  2015-01-03 11:30
I too find this very annoying.
Well my junk mail filtering has not worked since I "migrated" to Yosemite and it is very annoying. I don't know how you missed those threads at Apple Support Forums as there are many of them. If they don't fix it in the upcoming point release I will have to find a new client.
Joe Kissell  An apple icon for a TidBITS Staffer 2014-12-19 17:44
As I said, there are many bugs, and I only wanted to list some of the most prominent ones. I haven't had any trouble with junk filtering personally, but then, Mail's built-in junk filter has never been very good, which is why I use SpamSieve. I also recommend that people use server-side spam filtering if possible, because then the spam will be gone before you read your email on iOS devices too.
Jim Reardon  2014-12-20 01:25
As an Apple Mail user for sometime and a user of Gmail, the Mavericks debacle sent me fleeing to Mailplane. I tried going back a few times, but after awhile, I'm weaned.

Whether using the native Gmail interface or Mailplane, there is no reason to struggle with a product that Apple can't seem to get right. The Gmail interface is so universal that it can be thought of as another mail client. It just happens to be on the web. The fact that it is free makes it possible to pull mail from any server on the planet and present it in a uniform way, segregated by account.

Sure, it would be nice if the MacOS integration were a bit tighter, but the inability of the OS to work with a non-Apple client like Mailplane is yet another Apple failure.
Nicholas Barnard  2014-12-20 23:14
It bothers me that many consider the Gmail interface as "universal".

Google has definitely done something different with email and I respect them for that, but I find the way they've squished email around to be anything but universal.

IMHO, OS X Mail hews closer to other email clients (Pine, Eudora, Outlook) than Gmail's web interface does. FWIW, I don't really like Gmail's interface. My employer uses Gmail, I tried the web interface again, but I promptly installed Thunderbird on my work Windows 8.1 laptop..

That being said, OS X Mail is part of my email solution, not all of it. (Mine involves Procmail, Shell Scripts, Cron jobs, and some automator scripts...)
Kirk van Druten  2014-12-20 02:17
There is a growing thread (now 10 pages) on the Apple Discussions forum with users reporting an (annoyingly) intermittent text entry delay of 2-5 seconds while typing in Mail under Yosemite. These users (myself included) all report they never had the issue under Mavericks. The 10.10.1 update doesn't fix it. Bug reports have been filed and we're hoping for a fix - soon. Any press to help other users affected by this is appreciated.

Here's the thread:
michael Tippett  2015-01-05 22:14
add me to that count.
Andreas Frick  2014-12-20 05:08
I don't need exchange compatibility. Exchange is not an open protocol and therefore should not be used. But I already have problems in Mail of 10.8. The signature of digitally signed sent mails is not shown. Has this been fixed in 10.10? Hadn't any problems in 10.6. I think Apple should fix all the problems firstly before introducing new major versions. A one year product cycle is just to short.
Two new bugs I've seen and I haven't tried to look for patterns. My main account is IMAP with a couple of Gmails per day. When I delete a message from the Inbox it doesn't always go away right away. It still shows up in the list, but if I click on it, the message contents don't show. But it eventually goes away completely. I haven't tried to find out if there is a pattern as it's only a minor annoyance and I assume it will be fixed someday. The other is that if I change signatures, the original doesn't go away as it generally did before.
Michael Paine  2014-12-20 23:06
More bugs with Yosemite Mail:
Word wrap not working when viewing some emails:
Sorting by a different column header loses the view of the selected message:
Elliot Amiel  2014-12-21 12:21
A new problem post Yosemite is that I can't copy and paste an image (jpeg,jpg,png, etc) into an email. I have to attach it instead. Actually, I CAN copy and paste and the email looks fine but when I send it it turns into a little blue box with a question mark in it. The only workaround I found is attaching the file. Apple tech support is totally stumped, saying that it's a bug that they will eventually fix.
Lynne P  2014-12-27 23:06
I'm so glad you posted this. Same issue here. Since I was coming from an old macbook pro running Snow Leopard to a brand new one running Yosemite, I was sure I was doing something wrong. I discovered the work around on my own after recipients told me about the blue box ?. This sure makes emailing more cumbersome when you cannot rely on what you see (your message) looking like what will be delivered.
Paris Voutetakis  2014-12-23 01:10
Quite a useful article, especially the part about automatic configuration of settings that I had overlooked. Though we know about the merits of IMAP there are people like me that although have many accounts intentionally or out of necessity that have to use POP for some reason. So even the oldest thing arround we rely on it functioning properly. There was a bug in Maverics with the "account info" that was fixed in Ypsemite but has a new bug not showing the last received message. The reason this dialog box is important is that through that one controls what is left on the server. Oh, and by the way my mail is organized in 619 folders+subfolders by indispensable filters that may leave about 10 mails of about 80 daily from all my 5 active accounts in the inbox for manual housekeeping.
I really value this dedication to updating us on Apple Mail. I've had a weird situation since Mavericks and now in Yosemite where the email in the listing does not correspond to the email in the viewing window. It is off by one email (the adjacent email) - it's irritating but not a show stopper.
Anonymous  2014-12-27 00:00
For more than a decade I've paid for Yahoo Mail Plus, which for $20/year gave me ad-free mail, very good spam filtering, dozens(?) of temporary, disposable email addresses, the ability to add multiple addresses for domains I own, hundreds of user-created filters, email forwarding, POP access (only if wanted), larger attachment sizes than in the free mail version, and the ability to use desktop mail clients with my Yahoo account.

No other mail service offered the ability at anywhere near Yahoo's price for me to receive mail from my multiple domain addresses and send from them using Yahoo, while also being able to create throwaway addresses when I needed to sign up for something where I worried about later getting spammed.

At some point in late 2013 Yahoo added some features from Mail Plus to the free mail service, then killed off Mail Plus, replacing it with a "Premium" product for $50/year (while grandfathering in existing users at the old $20/yr price).

All previous features, disposable email addresses, filters and Pop&Forwarding, are now also available to free Yahoo Mail users!

I doubt it's worth that much for most people (which is probably what Yahoo intended) but there's no other service I know of which currently lets you have all the features I mentioned at such a low price ... and work so well for so long.
Suzanne R Brown  2015-01-05 19:50
Guess I'm very lucky! I have 3 separate email addresses (all .mac) and I have no trouble with Mail at all. I'm still using Mavricks as I have a 2009 iMac as well as new iPad and iPhone.

How did I get so lucky?
Michael H.  2015-01-05 20:57
I've given up on Apple Mail and switched to Postbox. My coworkers and I tend to have both personal & work email accounts backed by Gmail. While I'm more fortunate than the boss, who had Mail crashing on him all the time, I found myself having to do a "Rebuild Mailbox" operation once a week or so in order to have certain mail boxes keep their message list display in sync with the content they were showing. Plus, Mail was eating large amounts of CPU - looking at the activity, it would sometimes show 12 copies of "synchronizing X" at the same time.

I finally gave up when I realized that I was using the web interfaces for Gmail because it was faster, took less CPU, and was more reliable than Mail. Sigh.

(10.9.5, otherwise happy with my MBP.)
nrkmann  2015-01-05 21:41
All this is alright for the technocrat. However, my wife just wants it to work out of the box. If it doesn't work out of the box then she will move on to something else.
Matthew  2015-01-05 22:51
I have constantly disappearing top menus starting in Mavericks and continuing on into the new OS even after re-installing Mail. If I quit and restart they will re-appear, sometimes they will re-appear without a restart. And, the list of emails will then sometimes go through all the way to the top through the space of the disappearing menu. Go figure.
Tony Voss  An apple icon for a TidBITS Contributor 2015-01-06 02:56
More flexibility in email addresses, please. I use a separate string in front of for each organisation I deal with. It is a great insurance against email address leaking and getting spammed - only that one address is compromised. So I have a very long drop-down list to select from when composing an email. Apple SMTP can only handle a handful of such aliases which have to be verified. So I end up sending mail out via another route, while still using Apple IMAP. This works in OS X to date, but in iOS you cannot choose a different SMTP server for an iCloud account, so I have to fiddle around using Apple IMAP servers outside iCloud and setting up application-specific passwords for my Apple ID.

Please Apple - improve flexibility for outgoing email addresses. Malicious spammers/impersonators could be controlled by requiring verification on a domain basis rather than each address before the @.
Nicholas Barnard  2015-01-08 02:20
Tong, Here here!

I also have the same issue, both with my domain and a full subdomain my ISP gives me to work with..

I don't really mind the huge pulldown, but it'd be nice if there was a better way to add and delete addresses.

I guess I could pull the addresses from my config files, but that'd have alot of noise. (Perhaps yet another reason to move that to SQL from flat files.)

This is one of those things I miss about Eudora, you could manually change the headers to whatever you want.

Also, preventing spammers should more be a function of the outgoing SMTP server, not the mail client.

Also, I'm sniffing up an idea with Mail ActOn and some AppleScript.. Wouldn't be the cleanest, but it'd save some copy and pasting and manual work.
They seem to be working hard on getting ordinary IMAP accounts working less well too. Guess I reported like 50 bugs since Yosemite and with the latest beta it is working less well than with the first beta of Yosemite. Ordinary IMAP: Had a message just go up in thin air the other day on an ordinary IMAP account. Redirected messages does not show up as being sent.

GMail: when moving messages from the Sent messages box to the Inbox (as I have always done) then about 25% of the time the message list for the Inbox gets corrupted! Possibly this could happen when moving messages between other Gmail "labels/boxes" too. Almost always the corruption with mixed up headers are resolved by rebuilding the the message box. (I have rebuilt the index, vacuumed it etc. to no avail - the problems are persistent.) But there is a big chance of not detecting this in time when replying or archiving.

My favourite thing to complain about which has been a problem since Mountain Lion (I think) and a bug(!) that they apparently are not able to solve: you cannot use 'Send again' cmd+d on a selected message as you used to and as the menu suggested you should be able to do, unless you first open the message (and then you may accidentally resend the message without changing anything (as you most likely want a new To e-mail in there, or change something else) by pressing Cmd+d twice ... (rather unintuitive). Many other minor problems too and things that could be refined, but still using it.
Lane Dunlop  2015-01-06 18:05
The most frustrating part of Mail for me is the search function. When searching by a term, I get multiple copies of the same email show up, each a slightly different one as though Mail was saving the email every 15 seconds or so, which it seems like it is. This makes it virtually impossible to search for more common terms or emails from a few months ago as there are so many results. Is there a way to get around this? Thanks.
Nicholas Barnard  2015-01-08 02:15
Are you using Gmail? I've found that drafts tend to be saved like crazy, but not cleaned out when the final one is sent...

I don't have any great solutions at the moment thought...
I just upgraded to Yosemite and notice that when I hit "Reply" to an email the original message stays open. With Mavericks, the original email closed as soon as I hit "Reply". Any idea how to restore this in Yosemite. It's not a big deal (since Mac mail seems to be working, albeit more slowly), rather it's more of an annoyance.