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If you drag a file and hover over Dock icons, various useful things happen which are similar to Finder springing. If it's a window, the window un-minimizes from the Dock. If it's a stack, the corresponding folder in the Finder opens. If it's the Finder, it brings the Finder to the foreground and opens a window if one doesn't exist already. But the coolest (and most hidden) springing trick is if you hover over an application and press the Space bar, the application comes to the foreground. This is great for things like grabbing a file from somewhere to drop into a Mail composition window that's otherwise hidden. Grab the file you want, hover over the Mail icon, press the Space bar, and Mail comes to the front for you to drop the file into the compose window. Be sure that Spring-Loaded Folders and Windows is enabled in the Finder Preferences window.

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Mountain Lion Mail Perturbs Sending Behavior

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Since the publication of “Take Control of Apple Mail in Mountain Lion,” several people have asked me about changes in the way Mail in Mountain Lion handles the From address in outgoing messages. At first I didn’t know what to say, because I hadn’t seen anything surprising in my own testing, but as more and more complaints have poured in (including many in Apple’s discussion forums), it became clear something was screwy. So I set out to investigate. It turns out Mail in Mountain Lion does handle outgoing mail differently than before, and for some users, it can be frustratingly difficult to predict what account Mail will send messages from.

Apple Mail lets you set up as many different accounts as you need, each with its own outgoing mail server and one or more associated email addresses. When you create a new message or reply to an existing message, Mail picks a default From account for you, although you can choose a different account from a pop-up menu in the header area of the message. That’s all entirely appropriate, and has been the case for as long as I can remember.

However, in Mountain Lion, Apple significantly changed the rules by which Mail chooses the default From account for outgoing messages. As a result, if you don’t carefully (and manually) check each outgoing message, you might find that you’re sending messages from an unintended account. This can have serious consequences if, for example, you end up sending work email from a personal account or vice-versa. I didn’t notice this during my first couple of weeks using Mountain Lion because I nearly always send email from the same account, and I don’t lose any sleep if I accidentally send mail from a different address. But for many users, this change is a big deal.

How exactly has the behavior changed? Here’s what I’ve found, based on well over 100 experiments covering as many combinations of variables as I could think of.

In Lion and earlier, the behavior is as follows:

  • When replying to messages, Mail always sends replies from the account to which the message was addressed. This is true regardless of your preferences or where the message was stored.

  • When composing new messages, Mail uses the account specified in the Send New Messages From pop-up menu on the Composing preference pane (in other words, exactly what the command says). The default choice, Account of Selected Mailbox, means that the account associated with whatever mailbox is currently selected in Mail’s sidebar is the one that should be used for outgoing messages. However, if a local (On My Mac) mailbox is selected, or if no mailbox at all is selected, Mail chooses a From account according to some rule I’ve been unable to nail down, even after many tests. And, if you have a particular message selected, then regardless of where it is, Mail may choose yet another From account — again, without any immediately obvious logic.

In short, although Lion has some indeterminacy with the Account of Selected Mailbox setting, the behavior is mostly predictable — and when it comes to replies, it’s both consistent and logical.

On the other hand, in Mountain Lion, here’s what I’m seeing:

  • When replying to messages:

    • For messages stored in a server-based (e.g., IMAP or iCloud) mailbox, Mail uses the account associated with that mailbox — regardless of the account to which the message was sent or your preferences. That makes reasonable sense as far as it goes, and even though it’s different from before, it should yield the same result most of the time. But…

    • For messages stored in a local (On My Mac) mailbox, if Account of Selected Mailbox is chosen in the Send New Messages From pop-up menu on the Composing preference pane (as it is by default), Mail uses… um… some seemingly arbitrarily selected account. As with composing new messages in Lion, I’ve tried dozens of tests, and every time I think I’ve guessed the pattern (such as the topmost account enabled in the Accounts preference pane; iCloud first, then Gmail; the last account you sent mail from, etc.) I find an exception. I truly don’t know; all I can say is that Mail seems to pick the same account consistently as long as your account preferences remain unchanged. On the other hand, if a single account is specified in the Send New Messages From pop-up menu, Mail uses that account — regardless of the account to which the message was sent. (In other words, it treats replies the same way as new messages.)

  • When composing new messages, Mail uses the account specified in the Send New Messages From pop-up menu on the Composing preference pane. As in Lion, Account of Selected Mailbox is the default choice, and for server-based mailboxes, it appears to work the same way. But if no mailbox is selected, or if a local (On My Mac) mailbox is selected, Mail uses the account whose Inbox appears first (under the unified Inbox in Mail’s sidebar); you can drag Inboxes up or down in this list to change their order.

To illustrate why this might be a serious problem, consider a user who has three different POP accounts — say, a home account, a work account, and a family account. Messages from all those accounts are filed into various local mailboxes, perhaps automatically by rules. When it comes time to reply to one of these messages, the user should be able to count on the fact that the reply will be sent from the same account that received it, without further intervention. That used to be the case, but it isn’t now. So outgoing messages may be missed or discarded because they come from the wrong account, messages can cross between business and personal domains, and so on.

I have no idea why Apple made this change, whether it was intentional, why it wasn’t documented, or whether it might be changed back in the future. Because the change might have been deliberate, and might have happened for some good reason that I simply can’t discern, I hesitate to label it as a bug. But in any case the change requires more thought and effort for users, and on the whole I think it was a pretty bad move. If you think so too, choose Mail > Provide Mail Feedback and share your thoughts on the matter with Apple. We can only hope Apple changes this in an update to OS X.

In the meantime, I’m sorry to say I know of no way to return Mail to its pre-Mountain Lion behavior. Choosing a single account from the Account of Selected Mailbox pop-up menu will keep Mail’s behavior fairly consistent, although that may not suit your needs. Likewise, using only server-based mailboxes, if you can do so, avoids the most serious part of the problem. Apart from those admittedly weak suggestions, I can’t offer any advice other than to be aware of the change and remain vigilant when sending messages.

One final tip, courtesy of Christopher Stone on the TidBITS Talk mailing list: In Mountain Lion, you can assign a keyboard shortcut to change the From account of the message you’re currently composing, which may be slightly easier than using a mouse or trackpad to choose the account from the From pop-up menu. To assign a keyboard shortcut, open the Keyboard pane of System Preferences, click Keyboard Shortcuts, and then select Application Shortcuts. Click the + (plus) button and select Mail from the Application pop-up menu. In the Menu Title field, type the exact name and email address as they appear in the From pop-up menu — for example:

Joe Kissell <joe@tidbits.com>

Enter the keyboard shortcut you want to use and click Add; repeat if necessary for multiple accounts. The next time you’re composing a message and realize you want to switch the From account, press the corresponding keyboard shortcut.

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

Master Apple Mail in Lion! Along with the basics of sending and receiving email, you'll find help with special topics like attachment handling, searching, rules and smart mailboxes, integration with Gmail and iCloud, reading RSS feeds, digital signatures and encryption, notes, backups, and much more.
Join author Joe Kissell as he explains Mail's new Mountain Lion features—such as VIPs and Notifications—and walks you through the basics of sending and receiving email. Special topics include attachment handling, searching, rules and smart mailboxes, integration with Gmail and iCloud, digital signatures and encryption, and more.

 

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Comments about Mountain Lion Mail Perturbs Sending Behavior
(Comments are closed.)

Geoff Arnold  2012-08-08 01:16
You write that

"For messages stored in a server-based (e.g., IMAP or iCloud) mailbox, Mail uses the account associated with that mailbox — regardless of the account to which the message was sent or your preferences. That makes reasonable sense as far as it goes, and even though it’s different from before, it should yield the same result most of the time."

Most of the time, but not all. I receive project-related messages through various email accounts, and use Mail.app rules to gather them into project-based IMAP folders on my personal server. In the past, my replies were sent using the account (and From address) that the sender expects to see. Now they all appear to come from my primary account, unless I take the time to select an account from the dropdown.

Very annoying. And I should have caught this using the beta, but didn't. (Too many other bugs to worry about.)
I'm in a similar situation as Geoff.:

I have many domains that all send their mail to the same mail server inbox, and I use mail aliases for that mail account to respond appropriately.

If Mail.app is now only going to use the one "Reply to" address for each mailbox then this is definitely a problem.

Is it too much to hope that this will be fixed in 10.8.1?
Tom Pollard  2012-08-08 17:39
It'll only be fixed if Apple know about it and recognize how it's inconveniencing people. I think if you care about it, you need to file a bug report.
Nicholas Barnard  2012-08-08 21:50
Oddly, I have a server-based IMAP mailbox where I get email to multiple different accounts in two different domain names. I'm seeing the Lion behavior although I'm running Mountain Lion...
john Whitehead  2012-08-08 06:30
Even before these bizarre changes I struggled with the problem.

My suggestion to Apple via their feedback pages was that there should be a field in the Contacts database that associates an individual with the appropriate mail account and uses that for new mail messages and replies. An individual is either a personal contact, or a contact of one of the several businesses I run or represent. This relationship should take priority over contingent questions such as where a particular message happens to reside when I reply, for instance.

It's true that there is a very small set of individuals with whom I have multiple relationships, but these are typically friends made in the course of business and by definition they'd be more forgiving of error.

Does anybody know if it's possible to achieve this? I guess I'm looking for something that relates to Contacts and Mail as BusyCal relates to Calendar.

Ronald Lanham  2012-08-08 06:57
It's a bug.

From my own experience, Apple appears to be extremely concerned with Mail bugs so this will probably be corrected in 10.8.1.

I also had not seen this much earlier... but this is one of those bugs that can easily be missed while testing.
Brian White  2012-08-08 09:54
You write: "I have no idea why Apple made this change, whether it was intentional, why it wasn’t documented, or whether it might be changed back in the future."

Why not ask someone at Apple? Are they really that secretive that even an issue like this can't garner a response if someone in the professional Mac or wider tech community reached out to a contact within the company?

I guess the fact that doesn't take place answers my own question, but still....
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-08 10:09
I have no contacts at Apple who have anything to do with Mail, and historically, getting any answer from Apple to any question that begins with "Why" has been nearly impossible :-).

Joe
Brian White  2012-08-08 10:21
Thanks Joe. Yeah, I get it, and I'm certainly not unfamiliar with Apple's history in that regard. Still, whoever makes up the management team responsible for Mail must be aware of this (and just sticking to this example), and you'd think that they would want to address it in some way, especially once it becomes a story and the support forums are filled with questions/complaints. If it WAS an intentional change, how/why could they ever think it was a good one?

In a perfect world I guess we'd get a good answer :-)
Adam Engst  An apple icon for a TidBITS Staffer 2012-08-08 14:19
Yeah, getting answers out of Apple is nearly impossible. Even if you can get an internal contact, they can't speak on the record, and Apple PR will never comment on something like this.
Reto Studer  An apple icon for a TidBITS Contributor 2012-08-08 13:11
I believe the account ML uses when sending is the account you have listed in the "Mailboxes" sidebar under "Inbox". You can change the order by dragging the mailboxes.
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-08 14:58
In my testing, the From account chosen had nothing to do with the order of inboxes in the sidebar.
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-11 16:36
After further testing, I realized I was wrong—it is as you say. I've updated the article accordingly :-).
Sherman Wilcox  2012-08-08 18:19
FWIW (probably not much) I brought this to the attention of a Genius at my local Apple store. He denied that anything had changed in Mail that would result in this.

As I say, probably worth not much...
Joshua Smith  2012-08-09 10:20
The account it is defaulting to appears to be the first inbox listed in the "uber-inbox".

I've reported two bugs to apple (one for sending from "ON MY MAC" folder, and a separate one for creating a new message with the "uber-inbox" selected). They've already closed one of those as a duplicate, so I'm sure they are aware of these problems, and all indications are that they do not consider this a "feature".
I have figured this out, I think. It uses the first mailbox that you have under your "Inbox" as the default for mail that is not being created from a specific inbox. My solution was to move my preferred default inbox to the first position and now I default to that email account when I write new emails.
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-09 12:43
Two other commenters said the same thing, but as I mentioned above, that doesn't match the behavior I saw iny own testing. I have seen cases where Mail chooses an account that is not listed first.
Joe, sorry - I missed those comments. I'll observe behavior and check back if something changes. I have no mail "On my mac," it's all IMAP. Perhaps that is the variable.
JerryNaples  2012-08-09 14:16
I have all Tidbits communications moved (via rules) to an On My Mac folder.
This is where I am experiencing the Reply issues that Joe had discussed.

If, in the sidebar of Inboxes in Mail, I can force the reply to come from a specific email address by pushing that Inbox to the top of the list. But not all my replies to discussion groups (or associates) should come from the same email address.

So for now I will carefully look at the From address when creating a Reply. Sure hope that Apple fixes this in 10.8.1

Jerry Naples MUG
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-11 16:37
Well, I flubbed. Those who said the account used for new messages under Mountain Lion when no mailbox (or a local mailbox) is selected were correct—it's the account of the topmost Inbox. That still leaves plenty of mysteries, alas, but I've corrected that portion of the article.
Hilary Bok  2012-08-09 19:22
For me, the real problem is listservs, and particularly listservs I signed up for back in the dot mac days. Mail has decided that though I get mail from these listservs at my .mac address, it should send all my replies from my .me address, which of course the listservs don't recognize. Obviously I can just change all the messages by hand, but it's annoying.
I'm not seeing the behaviour reported. With the preference set to "Account of selected mailbox" then all replies/forwards etc use the account the mail was addressed to - what shows in the Mailbox column. For new mail, I consistently see what Steve reported - if you select Inbox on the left hand side it uses the top account. I can drag/drop accounts to reorder them under inbox and it always chooses the topmost account. If I choose a specific mailbox on the left hand side then new mail is always addressed from that account.

All my mailboxes are local to my Mac, so as has been said, perhaps it's something to do with local/server mailbox mixes.
Justen  2012-08-11 12:36
Off topic, I know, but it's about Mail in 10.8, so I thought I'd ask:

Does anyone else hate that the flagged mailbox is now permanently fixed near the top of Mail & that it can't be hidden as much as I do? I positively loathe it.
David Emery  2012-08-11 15:23
I noticed right away ML Mail.app's behavior had changed for the worse, and reported it as a bug. I didn't spend time running down exactly what changed, so I appreciate the explanation.

APPLE GOT THIS WRONG in Mountain Lion.
The above is just another reason I will not change from snow lepord- which allows me to use EUDORA !
Still going strong after about 20 years- can use IMAP or POP- and have virtually zilch problems even when using multiple mail addresses which are clearly displayed and easiloy changed from default and always trigger to return to sender plus return recipts

OH how I wish a GOOD update were available with same features
Mac Bakewell  2012-08-13 21:35
Dear Eudora! Started out as a Classic (OS 6) app in 1988, still works (for me) as well as ever in Snow Leopard, and can be included among a number of reasons why some 45% of Mac users never bothered with OS X 10.7. http://tinyurl.com/cnyeomh

I'm one of those 45%, but because I do anticipate eventually moving beyond Rosetta I've lately been trying to come to terms with Mail app. It's not been easy, and especially not after 16 years with Eudora, during which I've evolved a fairly complex and perfectly reliable arrangement which includes six accounts, over 100 mailboxes, and well over 200 filters.

Aside from Joe Kissell's TCo books on the subject (thank you, Joe!), the most helpful resource I've found is Indev software's MailTags, which adds to Mail app at least a few of Eudora's most essential organizational features.

Also encouraging is that MailTags (like it's associate app, MailActOn) is OS X 10.8-compatible, even as more than a few old-hand developers are struggling with Apple's increasingly restrictive "sandbox" policies.

So until this I was feeling like I might be making some headway, but now? Looks like yet another reason to be pleased to have spent bits of the past several years evolving an alternate environment in Gmail and Mailplane.

Fact is, I now mostly prefer Gmail's tag-and-search concept, for many of the same reasons outlined in Adam's excellent 4-part series on Zen and the Art of Gmail http://db.tidbits.com/article/12036, so I'm interested in Mail app really only because I spend several months each year on a connection so slow that any web-based interface becomes tedious.

From that perspective, my favorite parts of Mail app are its threaded messages and MailTags-enhanced smart mailboxes, and by combining those features I've come up with a customized variant of Mail app that works quite well. It's not Eudora, but it's pretty to look at and does do at least a couple of things -- notably Unicode and HTML -- that Eudora never quite understood.

So my coming to terms project has been coming along, but this Mail app reply-from thing is a broadside to every common-sense perspective I can imagine. One can only hope it's an unintentional bug that will be quickly remedied. I'm not holding my breath, but will join those sending feedback to Apple.
Mac Carter  An apple icon for a TidBITS Supporter 2012-08-13 20:42
I've always felt uncomfortable with the way Mail handles the default mail box. It has always seemed that if I didn't constantly pay attention to the FROM account, I could easily get caught sending a business message from my personal account and vice versa. Hope this gets sorted out soon.
Mac Carter  An apple icon for a TidBITS Supporter 2012-08-13 20:43
One semi-related question... Does anyone know why you cannot drag & drop a piece of text to the SUBJECT bar in Mail? Is there any logic behind this odd behavior or is another long time bug in Mail?
Mark Moore  2012-08-14 19:53
I just upgraded to Mountain Lion and i can confirm the same issues. Especially troubling is that, as others have noted, when incoming emails are filtered into local folders, ML Mail completely forgets what account they should be associated with, and then when one then replies to those messages, the "From" address almost invariably comes up as the wrong one (at least in a situation where a user has multiple accounts, as i do).

I just spent a good long time on the phone with a senior-level support specialist at Apple who was immensely helpful and determined to work with me to find the cause. I let him view my screen and I also sent him a big dump of my configuration files, which he's forwarding to the engineers in the hopes that they can find a solution. BTW, i also directed him to this article, so with any luck Joe's well-written description of the issues and the testimony of all you good people will be included in Apple's considerations.
Lewis Butler  2012-08-14 21:30
One thing that I have noticed is that if you have multiple emails associated with one account (like user@me.com, user@mac.com and user@icloud.com) you need to list all of those emails in the account settings, otherwise your email will always be sent from the account you do have listed.

Email Address: user@me.com, user@mac.com, user@icloud.com

In Preferences => Accounts => Account information.

I haven't noticed the other "on My Mac" related issue because none of my email is stored locally, it is all in server side IMAP folder.
Nicholas Barnard  2012-08-15 02:09
AFAIK, this is how it has been for a while -- you have to have all of the addresses listed otherwise I believe it picks the first one..

It won't allow you to put a from address that you'ven't said belongs to you. The opposite is fraught with huge huge problems.
michael  2012-08-15 06:00
I am surprised nobody here is also talking about Mail's vanishing cursor bug.
If I go to another app while I am composing in Mail, when I return to the email I was working on the cursor has vanished. I then have to click in the message area of another blank email to get the cursor to return. I keep a shrunk down blank email always open now for this purpose. Everyone I know has this bug in their Mail and there's more on it here...
https://discussions.apple.com/thread/4156726?start=0&tstart=0
Chris Kohuch  2012-08-15 22:51
I'm not able to duplicate this behaviour at all on my machine. Obviously, a large number of people from your experience are encountering it, but it is equally clearly not a bug that is occurring for every Mac running Mail under Mountain Lion. Best of luck solving it though. Let's all hope that 10.8.1 covers a multitude of sins (I myself have had nothing but problems with Mac to Mac screen sharing since upgrading to Lion).
Shuji HOSOKAWA  2012-08-16 20:52
Makes perfect sense.

If you are in an account, mail is sent from that account.

When did it stop being the users fault that they cannot figure out which mail account they are in? It's not that hard.
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-16 20:54
It's a problem if you receive mail from many accounts but store the messages in a central location (or in another account). Many mailing lists, for example, accept email only from certain addresses. It used to be that you didn't have to think about that—just reply, and the message is being sent from the right address. Now you have to second-guess Mail every single time.
Shuji HOSOKAWA  2012-08-16 21:31
There is no second guessing.
Just look.

Sure it would be nice if you didn't have to think, but who would be blamed if something went wrong?

This way the onus is on the user to ensure they get it right. No doubt it will improve over time, but the user should always be involved in the decision making.
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-16 21:56
Sorry, but you're ignoring the fact that Apple changed something that was working pretty well to make it far more inconvenient. Maybe it doesn't bother you, but it's enormously irritating for lots of people, and it's not helpful to say, essentially, "just get over it and pay more attention."
I just upgraded to 10.8.1 and this behavior has not been fixed.
Alex Norton  2012-08-24 04:25
Actually, I think Mail got it right. How is it suppose to know the account you received email from if it was addressed to an email alias or group like customers@somebigcompany.com? What if you were BCC'd so your email account isn't actually in the email headers?

How did Mail perform before Mountain Lion if there was no explicit email address it could match to your accounts? Would it just guess?

Sounds to me like they improved the feature by taking away the guess work for situations like these and made it more reliable and predictable.

I think the only logical thing Mail.app can do is reply from the address that the account is sitting in. That makes a whole lot of sense to me.

I admit, I don't have a On My Mac local account and I reply from the account I was addressed. I don't understand why some people are moving messages to a local folder. Mail works great without a network connection for me. It caches all of my messages so I can see them when I'm not connected
Joe Kissell  An apple icon for a TidBITS Staffer 2012-08-24 04:55
The pain point here isn't the From address, it's the From account. Prior to Mountain Lion, Mail based its decision on the _account_ in which you received the message, not the _address_ to which the message was sent. That was predictable; its current behavior is much less so.
Samuel Herschbein  2012-08-31 18:30
FWIW: before I read this article I filed a bug report.

IMHO this is a bug, since nobody can figure out a logical reason for this non-deterministic behavior.

I also left feedback and encourage others to do so.