iOS 7 has bug in handling attachments on S/MIME Encrypted Mail

Today I completed the following tests…

Preliminary Configuration

1. Wiped (Settings > General > Reset All Content and Settings) a 3rd-generation iPad that had recently been upgraded to iOS 7.0.4.
2. When the iPad came back up after the full reset, I selected English, United States, Use Cellular Connection, Enable Location Services, Set Up as New iPad, Skip This Step (Apple ID), Agree, (create a passcode), Use Siri, Don’t Send, Get Started.
3. Plugged the iPad into my Mac. iTunes launched. I Quit iTunes immediately. No apps were synced to this iPad beyond what are included with iOS.
4. Launched the iPhone Configuration Utility 3.5 for Mac. Applied a Configuration Profile containing my e-mail account settings, S/MIME security certificates, Wi-Fi settings, VPN settings and other information.
5. Unplugged iPad from Mac. Closed iPhone Configuration Utility.
6. Prior e-mail started flowing in from the accounts included in my Configuration Profile.

Test 1 - Verify Encryption

From a separate Windows computer running Microsoft Outlook 14 - part of Microsoft Office Standard 2010 - I sent an encrypted e-mail from a mailbox residing on Microsoft Exchange 2003 to the same mailbox. My iPad’s Configuration Profile includes access to the Exchange account, as well as the S/MIME certificate. I received the message on the iPad. Confirmed that the check-mark and lock icons were present, indicating that the message was both signed and encrypted. I was able to read the text content of the message just fine.

Test 2 - PDF Attachment, From and to Exchange, Sent via Outlook

From the Windows PC running Outlook, I sent an encrypted message from and two the same Exchange mailbox again, this time including body text and a PDF file attachment. On the iPad, I again noted the check-mark and lock icons at the top of the message. I could read the text in the message. But the PDF file attachment appeared for only a second before disappearing altogether. Had I not been watching it at the exact moment that I opened the message, I might assume that the message bore no attachments.

It’s important to note that iOS 7.0.4 is the first time where I’ve seen the attachment icon disappear on encrypted messages. So far I’ve only observed this on PDF files, and only on the iPad, not iPhone. An iPhone 4 running the same configuration profile will show the PDF attachment pulsating.

Test 3 - PDF Attachment, From and to Google-hosted IMAP, Sent via Outlook

From the Windows PC running Outlook, I also have access to a Google Apps account configured to use IMAP. Sent an encrypted message bearing a PDF attachment from one Google-hosted IMAP account to another. Received message on iPad. Confirmed check-mark and lock icons at top of message. I was able to read the message text. The attachment icon pulsated a couple of times and disappeared. Again, this disappearing seems to be a new twist in iOS 7.0.4 on iPad only.

Test 4 - Word .DOC Attachment, From any to Exchange, Sent via Outlook

Repeated test 2, this time with a Word .DOC file attached. Received message on the iPad. Confirmed that it’s signed (check-mark) and encrypted (lock). I’m able to read the text of the message. An icon for the Word doc is visible and pulsating rapidly, exhibiting the same symptoms as the original problem. After leaving it sit and pulsate for around 30 seconds, the Mail app closed on it’s own. Re-launched Mail, and opened the message. It continued pulsating. Attempted to open the attachment, and received no response.

Test 5 - Word .DOC Attachment, From and to Google-hosted IMAP, Sent via Outlook

Sent using Outlook 14 an encrypted message from one Google-hosted IMAP account to another bearing a Word .DOC file attachment. (Had to interrupt the test at this point, as the 3rd-gen iPad became unresponsive to the home and power button input. Resolved by holding both buttons for fifteen seconds to force a reboot.) Opened the latest test message, confirmed encryption, and was able to read the text in the body of the message. The .DOC attachment is pulsating rapidly and will not open.

Test 6 - PDF and DOC Attachments, From and to Google-hosted IMAP, Sent via Apple’s Mac Mail 7

Using the same PDF and DOC files as earlier, I created an encrypted message on my Mac using Mail 7.0, sent from and to separate Google-hosted accounts via IMAP. While adding the attachments, I used the option to Send Windows-Friendly Attachments. Received the message on the iPad. Confirmed that it was encrypted. The PDF file is displayed inline, as if it was part of the message body. The icon for the DOC file is visible, and not pulsating. I can open it.

Now I could could go on creating a number of additional tests, and may consider doing so for anyone with an apple.com e-mail address, or the address of an organization who is also trying to overcome this bug that Apple introduced in iOS 7. I can be reached at the only e-mail address displayed in the moving GIF of my original blog post.

Thanks.

While iOS 7.1 resolved the pulsating attachment issue on S/MIME encrypted messages, I've seen a curious issue since upgrading. On at least three encrypted messages bearing attachments, the filename shown was that of an attachment previously received on an earlier message. At Apple's request, I wiped an iPhone 5s running iOS 7.1 and set it up as if it were a new device. I haven't been able to reproduce the issue since.

Obligitory long-winded blog post here.