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I seem to have found a bug in the SMTP implementation on the iPhone’s Mail.app. When the iPhone sends an email the recipient will actually see two distinct senders, one sender is “Appleseed” and the other is “John” . Both sending addresses will be wrong and un-reply-able. Somehow, during the SMTP conversation, the iPhone is mishandling the from address if the display name contains a comma.

At work we have a naming convention for email addresses as:

"Last, First" <last_first@Domain.EDU>

For example, assume your email account is set up like this:

Name: Appleseed, John

Address: Appleseed_John@Domain.EDU

When the iPhone sends email the recipient will actually see two distinct senders, one sender is "Appleseed" and the other is "John" <appleseed_john@Domain.EDU>

The sending account should of course be: "Appleseed, John" <appleseed_john@Domain.EDU>

I’ve tested this out sending email from the iPhone through various email servers and I’m fairly certain the bug is on the iPhone, as it happens no matter which SMTP server I use. If the email account has a comma in the display name the message will have a corrupt “From:” address, and the recipient will be unable to reply (since the address gets munged in transport).

I’ve also tested this out with other email clients, and they all properly send email from accounts with “Appleseed, John” as the display name.

(posted on the apple forums here)

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worst. night. ever. I was helping a friend of mine change his Apple OS X Mail.app account settings to use his new mail host last night, and in doing so accidentally deleted all of his mail. Here’s what happened:

I added a new account to mail.app to check emai, and deleted his old account (since he couldn’t check that account anymore). Upon deleting the old account all of his messages instantly dissapeared… NO WARNING AT ALL. As soon as I hit the minus button I could see all the email in the background being quickly deleted. Not deleted to the trashcan or deleted items… but just instantly deleted. I had to try a undelete program to recover some of the messages off the hard drive.

1) There was no warning or “are you sure” type message. Every message that the account had ever received or sent was simply gone.

2) Why not send them to the trashcan or deleted email folder? Nice thinking apple.

3) Sure, there might be a technical reason behind this, but in my opinion it’s silly to bind email messages to email accounts. Deleting an account should have nothing to do with deleting email messages. Messages should not be tied to mail accounts, or at least make that marriage more visible and give the option on deleting an account with messages that would move messages to a global inbox.
I posted the problem on the official apple discussion forums:

apple forums, apple forums

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