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Oh dear, not having much luck at the moment. Having recently wasted hours on a simple problem, I've transferred my anti-Midas magic to a friend, and lost some email data. Could someone advice (a) whether the below was an obviously stupid idea, and (b) if I can do anything in the way of recovery?

So, my friend uses Hotmail via POP3 in Mail, in Mac Lion on a MBP. This is set to delete mail in a week after it is read from the server (although she trims mail manually in the Hotmail web interface, and is fairly sure old mail wasn't being deleted, since she still has very old mail in her web-based inbox).

OK, so she's started a new company, and has purchased a domain/hosting package, and needed assistance setting it up. The requirement was that mail should pool in her Mail inbox together with Hotmail, but she should have a profile widget in the New Mail interface that lets her set which email address each message should come from.

Easy enough, I reasoned. The domain was already set to forward to her Hotmail address, so the hosting company is not doing any mail holding - just sending it on. I figured that creating a new mail profile which had all her Hotmail credentials except for the From address, which would be the info@example.com address we were setting up, would do the trick. Now, at this stage you're thinking:

  1. that's worth a go,
  2. that won't work, or
  3. don't do that, you'll break it!

I'm hoping you're not thinking 3, since I went ahead and did that, and although the profile created, it caused an error, and did not appear to work. The error was:

The account path /Users/<name>/Library/Mail/V2/POP-<email>@<pop3-server>
is already being used by the account "Hotmail".

"OK", said I - and duly deleted the newly created "MyDomain" account. Sadly this removed the inbox, drafts and sent items related to the (perfectly functional) "Hotmail" account (which I didn't touch). A call to Apple support in India resulted in the specialist logging a call - and he seemed amenable to the idea that, since the profile popped up that error when we saved it, it should have warned us that it was about to do something catastrophic. I offered to log a bug with Apple via the web, but he said there would be no need, since he'd already done it.

So, either I hit against a Mail bug, and I should be hopping up and down, or I did something perfectly stupid, and I should be sitting in the naughty corner for a few hours. Honest thoughts very welcome on this point.

Meanwhile, my friend and I - in the absence of backups - are trying data recovery software (Disk Drill) to get back the mails that have been lost. We will see if this works tomorrow, but if any other ideas are forthcoming, I am all ears. We've dug into the Hotmail mail folder, and the important-sounding folders are 40KB or so - i.e. basically empty.

Help! and TIA.

Edit: it's a long shot, but my friend might have been running iCloud. Should this back up all her email, or just me.com email? We went into the interface and couldn't see anything under email (everything seemed empty) but I guess that might be because she wasn't logged in, or iCloud doesn't back this stuff up, or it wasn't running...

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What does the directory /Users/<name>/Library/Mail/V2/ contain? –  AndrewNimmo Jan 8 '12 at 14:32
    
Forget iCloud, it's not related to what you've been doing. –  AndrewNimmo Jan 8 '12 at 14:33
    
No backups? Critical information should always be backed-up. Get an external disk and setup Time Machine. –  AndrewNimmo Jan 8 '12 at 14:35
    
@AndrewNimmo - that folder contained several sub-folders, and the one pertaining to the (untouched) valuable account, had a few default folders in there ('inbox', 'sent' or similar) - and they were very small as I say. It seems that my actions in re-adding the same account, which in hindsight the application should have gracefully rejected - reset the account-specific folders to empty. –  halfer Jan 8 '12 at 17:44
    
On backups, I agree. I will help my friend configure Time Machine as a matter of some urgency. –  halfer Jan 8 '12 at 17:45
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2 Answers

up vote 1 down vote accepted

If I'm reading the initial question correctly, you wish to select which account new mail comes from.

In Mail prefs > Accounts > Account Information tab you can enter multiple email addresses in the Email Address field. You must separate them by commas.

Mail prefs

When you create a new message The From dropdown will list every email address. These addresses will be used in the From: field.

Mail From

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Gah! As easy as that? Yes, that was exactly what I was trying to achieve. If only the UI made that clear. Dammit! ;-) –  halfer Jan 15 '12 at 14:17
    
I wish I could split the +100 between the answer from MattiSG and you - this was very useful indeed. So, you get a tick and a +1 :) –  halfer Jan 15 '12 at 14:29
    
Not to worry. The idea is to get the answers you need. –  afragen Jan 15 '12 at 17:48
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Why the mail was lost

Mail.app saves data for each email account, indeed, in the following folder structure:

~/Library/Mail/V2/POP-<email>@<pop3-server>

One folder for each unique mailbox.

So, of course, if two emails actually use the exact same <email> and <pop3-server>, you can see that there will be a conflict: both their data would be stored in the same folder, which would conflict on each and every mail / state save.

Mail.app warned you about this (though in a very user-unfriendly way. It should have said you can't have two accounts with the exact same username and server). However, where it seems to have bugged quite severly, is that it did create the account in its registry, even though it said it couldn't. So, when you deleted it from the registry, it also went on to delete the data associated with the account. This data was in… well, ~/Library/Mail/V2/POP-<email>@<pop3-server>. So, it deleted the data for both accounts, effectively falling into the conflict it had tried to avoid.

The “duplication” idea

You're asking if duplicating the account was a “good / let's try / oh-no” idea. I'd say, it's neither. It's just a “won't work & not really useful” idea. If the hosting (publicly-visible) email was set to redirect to hotmail, then all the mail that was needed to check was in hotmail.

Sender → email@company → hotmail → Mail.app
         ↑ not saved     ↑ not saved
         upon transfer   upon POP dl

Why create another account with From changing? To be able to send mails that would only show the publicly-visible @company email? Then you did it wrong. Not wrong as in “you'll break it”, but wrong as in “you didn't know how mail works and made a wrong assumption”.

Mails are sent using the SMTP protocol (a protocol to send, like POP is a protocol to download mail from a server). Changing the From header would not have been a guarantee that everything would have worked as expected. Indeed, hotmail would have probably (I can't be sure because I don't have any hotmail account, but in my experience most providers do, especially web-based ones) refused to send that mail.

Think about it: you would have asked hotmail's SMTP servers to send a mail pretending to come from an address that is not from hotmail. It's like asking UPS to deliver a package that has a competitor's stamp. The main reason this is extremely rare is that it would allow spammers to use such a service to deliver millions of emails without being caught: the mail pretends to originate from @whatever, but is actually sent from @hotmail. How could anyone trace this?

Whose responsibility it was

So, since you seem to be wanting mostly to assign blame:

  1. Mail should have been more explicit in its error message; that's not a bug, but that's bad UX.
  2. Mail should not have let you validate the account creation upon error. That was a bug, which became critical upon the edge case that you fell in: having another account with the exact same settings, and wanting to delete one of them.
  3. The idea of duplicating the account was not a good one, but should never have had such consequences. The assumption you made was false, but there is no doubt it is entirely the software's fault if data loss occurred.

As a matter of fact, data loss would not have happened if Mail.app had used a different file hierarchy (not to say it should have, it is much better this way than with useless ID numbers; but I mean it is the implementation that was chosen that is responsible, not the mail setup). They should have seen the edge case of multiple accounts being set up and either completely forbidden multiple accounts creation or not deleted data as long as one account uses the said folder.

Next

  1. BUY AN EXTERNAL HARD DRIVE AND SET TIME MACHINE UP. We all learn about this the hard way, and it is one such occasion.
  2. Forget about hotmail. Seriously. It is a shame to use such a client. Even if you don't use its web interface, it is bad. It has terrible spam filtering, does not support IMAP (at least to my knowledge), has poor file size limits… Get an account on a serious mail provider such as Gmail or Y!mail: web interface is excellent, quotas are much higher, attachments size is twice as big, the spam filtering is great, and they support IMAP.
  3. Use IMAP. We all agree that emails are most of the time critical pieces of information, especially in a business setting. IMAP will let you synchronize state (such as read / flagged), and keep a copy of all mails on the server. This way, you will get three backups: one online, safe on your provider's server. One synchronized, on your main computer. One offline, in case of an accidental deletion, in the Time Machine backup you've set up in #1.
share|improve this answer
    
Thanks for your detailed reply. Initial thoughts: (1) of course back-ups should be made, but it's not my computer - I work with the system as it is presented to me. Of course, I should have taken a backup before fiddling - now I know! (2) My friend uses Hotmail/POP3, and I don't want to change it. (3) Good idea. Once I'd switched from domain forwarding (to Hotmail) to using the email services on the new domains, I used IMAP for this, which sit alongside the Hotmail/POP3 configuration perfectly happily. –  halfer Jan 15 '12 at 14:17
    
I disagree with your assessment about using "hotmail's SMTP servers to send a mail pretending to come from an address that is not from hotmail" - this is a common configuration that I've used many a time (though not with Hotmail). Authenticated SMTP makes it very easy to send mail with different From/Reply-To headers - if spamming occurs, the SMTP server owner will respond to abuse complaints by deactivating the SMTP credentials. –  halfer Jan 15 '12 at 14:24
    
Since this does answer my question, you get the +100... thank you again. I'll give the tick to @afragen simply because that was very useful as well, hope that's ok! –  halfer Jan 15 '12 at 14:28
    
Incidentally, I am led to believe that Apple now knows about these bug(s). Any ideas if I can track their progress? I presume they don't have a public bug tracker! –  halfer Jan 15 '12 at 15:12
    
@halfer About SMTP authentication: feel free to edit my answer to add these details, I did not think hotmail would support it, seeing they do not support IMAP. As for the tick / upvotes / bounty: do as you please ;) Upvotes are not limited and can be given to everyone; to me, the tick is important only for future users, so they know what exactly answered your question if they ever have the same problem. For Apple tracking, I don't know exactly. Radar is for devs, and I don't know if you can get updates even as one. Maybe someone else knows? :) –  MattiSG Jan 16 '12 at 8:00
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