Mail: Default Reply-from Incorrect

I post this in the Apple Support Forums and also sent a bug report to Apple. I am posting here to see if anyone has a fix or if we can nudge Apple to quickly fixing this.

I have a total of eleven (11) e-mail addresses, which include my iCloud account. The majority of the addresses are POP3. I have that many addresses because of my business and each e-mail is for a specific web site. In order to sync my e-mails across the multiple computers I have, I created a rule that would move every e-mail I received to the iCloud account.

In Lion, even though the e-mail was moved to the iCloud account, when I replied to an e-mail, it would reply from the account to which the e-mail was sent. Thus, if an e-mail was sent to 'tony@mydomain.com', it would be moved to the iCloud account (which would sync it among all computers). Replying to it would be sent from 'tony@mydomain.com' and use that server and its settings.

This has been broken by Mountain Lion and Mail 6.0. Now, an e-mail is received and moved to iCloud. But, when replying, the reply-from address is now the iCloud address -- NOT the e-mail address to which the e-mail was sent.

This STILL works in Lion. I have a machine running Lion and have been using it side-by-side with MountainLion.

Now, a couple of things I have discovered.

While entering e-mail aliases into the e-mail address of the iCloud settings seems to work, it actually causes a couple of problems. First, it causes the iCloud syncing to not work -- the "Mail" box becomes unchecked in System Preferences for iCloud and won't stay checked so long as the "foreign" (non-iCloud) e-mail address is in the account settings for iCloud.

Second, the server settings for the outgoing e-mail get broken. It's weird. E-mails don't send at times.

I sincerely hope that Apple fixes this. People may suggest that I use IMAP accounts to sync my e-mails. That is not an option. The web host I use only allows a certain number of processes to run. With all my e-mail accounts, checking my e-mail would easily blow me past that number.

Thank you for your attention to this issue.

All the BEST!

T.

YakkoW said:

Yeah, I'm not even using iCloud in Mail and I'm having the same problem, where Mail in Mountain Lion is choosing the wrong "From" address to reply to a message. I'm not sure if that's a bug or if they intended to change it for some reason, but I definitely preferred it the way it was!

Click to expand...

Yes, it's looking like it's either a HUGE bug or a new "feature." If the latter, then I hope that Apple reconsiders and doesn't pull an Exposé-to-Mission-Control "improvement" on us.

Actually, the more I use Mountain Lion, the more cracks I am beginning to find. Mail is VERY buggy. There are numerous bugs being reported on Apple's Support Forums, from the issue described here to mail alert sounds not playing to SMTP errors when sending e-mails.

I was REALLY hoping that Apple was going to get Mountain Lion correct. So far, we haven't reached the top of the mountain.

T.

YakkoW said:

I've figured out what is (I think) causing the "reply from" problem. I posted about it here:
https://discussions.apple.com/message/19102145

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I think that your conclusion is correct: Mail replies-from the inbox in which the e-mail resides. I also think that your solution works in some circumstances.

It won't work in mine and others', though. I have a rule that I made in Lion that moved ALL incoming mail to my iCloud account. Why? So that I can sync my e-mails over my machines. It worked and was VERY sweet. When I replied to an e-mail, it used the account to which the e-mail was addressed.

Now, not so much. Obviously. Now, I can either have ease of replying and no sync or inconvenient replying and sync.

The scary part is that we don't know if this is a new "feature" that Apple plans on keeping or a bug that they plan on fixing. If the former, then I just may go back to Lion.

Thanks for your suggestion, though.

T.

sidewinder said:

What happens if you put the second address in the "Email Address:" field for the "work" account (Preferences -> Account Information)?

Something like this:

Email Address: bob-work@example1.com, bob-home@example2.net

What happens if an email sent to "bob-home@example2.net" shows up in the "work" account and you respond?

S-

Click to expand...

That DOES work. It screws up the iCloud sync, though.When I did that, I got the correct reply-from address, but syncing stopped. When I checked my preferences, the "Mail" box in the iCloud Preference pane was unchecked. So, I rechecked it. It didn't stay and reverted to unchecked -- and no sync through iCloud.

Thus, that takes me back to syncing versus ease-of-reply.

I and many others just want the functionality we had in Lion.

T.

sidewinder said:

It's not screwing up my iCloud sync for email.....interesting.

Scott

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Quite interesting. Is the "Mail" setting still checked in the iCloud Preference Pane?

T.

sidewinder!

OK, I checked again. You're right, the syncing DOES work. The setting DO become unchecked in the iCloud Preference Pane, but that does not appear to impair functionality.

BUT... Another issue rears its ugly head.

The e-mail doesn't send. Mail gets "confused" about what outgoing mail server to use and the e-mail gets trapped in the outbox.

*sigh*

I just want my Lion functionality back.

T.

sidewinder said:

AuPhalanx,

What happens if you setup just one SMTP server (authenticated)?

That's what I do and it seems to work fine...

Scott

Click to expand...

That's an interesting idea. I am going to play with it tomorrow and see what results it yields.

T.