Migrating Garbled iPhone Sent Items

We recently performed an Exchange migration for an Australian customer on Exchange 2003 and whose users occasionally rely on iPhones to send business emails. After the migration completed, they asked us why some emails sent using iPhones appeared garbled when accessed using Exchange 2010. Here is what we discovered and how we updated our service to automatically repair corrupt iPhone messages.

Normally, sent email messages are stored as MIME content which may look as follow:

  • Received: from 10.130.110.41 by e-srv.bar.edu with Exchange Server HTTP-DAV;
  • Mon, 1 Jan 2010 16:50:10 +0000
  • Message-ID: <35CEL53F-1AB3-2484-9885-5ACB73FA6D75@bar.edu>
  • From: “John Doe” <jodoe@bar.edu>
  • To: “Jane Doe” <jadoe@bar.deu>
  • Content-Type: text/plain;charset=”us-ascii”
  • Content-Transfer-Encoding: 7bit
  • thread-topic: IPhone Test
  • Subject: IPhone Test
  • MIME-Version: 1.0 (iPhone Mail)
  • Date: Mon, 1 Jan 2010 16:50:10 +0000
  • <message content>

However we found that messages sent using iPhones had the following prefix lines, which are invalid:

  • MAIL FROM: <jodoe@bar.edu>
  • RCPT TO: <jadoe@bar.com>
  • Received: from 10.130.110.41 by e-srv.bar.edu with Exchange Server HTTP-DAV;
  • Mon, 1 Jan 2010 16:50:10 +0000
  • Message-ID: <35CEL53F-1AB3-2484-9885-5ACB73FA6D75@bar.edu>
  • etc.

Indeed, the first two lines are SMTP envelope instructions which should NOT be stored with the message’s MIME content. Because of these invalid lines, some email clients will assume that the encoding is plain text when it is binary. As a result, depending on the selected encoding, some messages will render binary content as text and so appear garbled.

This is not the first time we’ve modified our service to repair corrupt or invalid MIME content. For example, we know that some Exchange messages have a missing TNEF-correlator header field which we already automatically repair. However, this new situation demonstrates the agility we get from running a cloud-based migration service. Moving forward, all our customers will benefit from our automatically repairing corrupt iPhone MIME.

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Posted in Features & Services, Mailbox, Microsoft, Tips & Advice
One comment on “Migrating Garbled iPhone Sent Items
  1. [...] detailed error reporting, MigrationWiz uses advanced strategies such automatically repairing corrupt MIME content, handling dropped connections, or dealing with misconfigured [...]

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