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IMAP, Mail and the iPhone

I finally switched to IMAP for my main Gmail account on the occasion of getting an iPhone. I was diligent and did all the ‘recommended’ extra configuration:

  • In Mail.app’s account preferences, checked: ‘Store sent messages on the server’
  • Selected the ‘Sent messages’ folder in the GMAIL folder in the Mail sidebar and via Mailbox->Use this Mailbox for->Sent

However, no email sent from my Mac or from my iPhone using the gmail account  showed up in the sent folder in gmail. Nor was any email sent from my iPhone stored anywhere. After a total of my maybe eight hours I had eventually figured it out.

The problem is Mail.app and even more so the iPhone.

The point of IMAP is to have synchronized read counts (and deleted mails, etc.) and synchronised folders in multiple locations including the server. The most import folder apart from the inbox might arguably be the Sent Messages folder.
With multiple email accounts if one has not consolidated both the receiving and sending in one (IMAP) account (or does everything locally in Mail.app) one usually wants to have control which server sends and stores the sent messages (since sending to a server which is accessed via POP won’t store the messages anywhere).
That is why in Leopard, Mail acquired the possibility to send emails from a given account only with a specified smtp server.

And that is where things break down. If Mail cannot reach the specified smtp server, it asks after a short while whether it should try a different server. I run into this issue almost daily since at work only my work smtp server is accessible and at home my work smtp server is not accessible. The problem is that Mail than sticks to that manually selected alternative server until that one fails AND there is no possibility to know which smtp server Mail is using at any given moment (apart from sending an email to oneself and examining the header). And on top, there is no simple way to reset the smtp server (my solution is to make an smtp server inaccessible and then see whether Mail fails, if yes Mail is currently using this server for this account, in case of failure I can also select an smtp server manually).

What is even worse that this alternative smtp server is now (without you knowing it) ‘synched’ to the iPhone. And if you examine the account on the iPhone, the smtp you originally selected is still listed even though the iPhone using a different one. And even if you fixed things in Mail, synching won’t fix it on the iPhone you have to reset it.

And Gmail? Well, it just got the beating because it is so darn convoluted that everybody seems to give you different directions of how to configure it. Who would have thought that the smtp listed for an email account on the iPhone is not the one actually used.