Getting iPhone mail working from outside on iOS4

This past week has been rather quiet but not in the way I'd hoped. Normally when I'm on the road as I was this week I'd get a series of photos and videos of the various things going on at home. While FaceTime is great and we had some great calls the videos and photos weren't coming.

As it turns out this isn't some issue with a lack of good intentions. In fact my wife was certain she'd sent them. Indeed there on her iPhone was an outbox full of messages to family members waiting for the last week to be sent.

It also turns out that she's far from alone in having these issues. And before Apple feels the need to post videos of other phones failing in the same way, yes there are other phones having similar problems that aren't running iOS4 or made by Apple.

At the same time my phone is having no issues sending photos and videos from the photo gallery. So I started to compare the differences between the two phones.

My phone carries this set of accounts:

  • Mobile Me (FindMyiPhone, Contacts)
  • Google apps #1 (IMAP mail)
  • Google apps #2 (IMAP mail)
  • Google apps #2 (Exchange Calendar sync)

while my wife's was similar but only had one mail account:

  • Mobile Me (FindMyiPhone, Contacts)
  • Google apps #1 (IMAP mail)
  • Google apps #1 (Exchange Calendar sync)

In both cases Google Apps #1 is the default account responsible for sending mail from outside the mail app. And in both cases mail works fine in both directions from within the mail app.

Now where things got interesting is that if I enabled mail on the Google Apps #1 Exchange account the messages in the outbox would be processed for the Google Apps #1 IMAP account right away. Now, of course, she's got duplicate inboxes and duplicate messages right and left. The next step was to try with only the Exchange account. This too failed.

So before going too much further it seemed some combination of deleting accounts and rebooting the phone was helping many of the folks on the discussion board. Indeed by deleting the two Google Apps #1 accounts on her phone and rebooting the problem has gone away.