iOS 7 Mail App Flaw

Pulsating Attachment Problem in iOS 7 Mail App ©Apple Inc.

Pulsating Attachment Problem in iOS 7 Mail App ©Apple Inc.


 
It seems that relatively few people are aware of commonly-available standards and tools for end-to-end e-mail encryption, though more may be interested in this topic in the post-Snowden era in which we now find ourselves.  One of these standards – S/MIME – is natively supported in most e-mail clients, including Microsoft Outlook, Mozilla Thunderbird, Novell Evolution, Apple’s Mac Mail, and the iOS Mail App (in iOS 5 and later).  A small handful of colleagues, business partners and I use S/MIME signing – and encryption where applicable – in our day-to-day e-mail communications.  The fact that iOS has supported S/MIME for awhile makes it fairly seamless to use this technology, whether at our desks or on the go.  That is, until we all upgraded to iOS 7.

Having upgraded our iDevices to iOS 7 on or very shortly after the September 18th launch, we quickly noticed something strange with regard to encrypted e-mail.  We could read the body text of encrypted messages just as before.  Unlike with iOS 6, however, any attachments on these encrypted messages appeared to pulsate rapidly as seen above.  Trying to click on a pulsating attachment either results in nothing, or in the Mail app closing out abruptly.  Though the pulsing is fast enough to make it difficult to discern with the human eye, the attachment icon bearing the file type and name is sometimes interspersed with the word Downloading, the file name and a size that doesn’t seem to increment.  We’ve been unable to open any attachment exhibiting the pulsating behavior.

On Friday, we assumed that this affected all S/MIME attachments received on devices using iOS 7’s native Mail app.  I contacted Apple Support on case number 507281855, and also sent a message to a customer relations e-mail address that I’ve corresponded with in the past.  As we looked into the issue further over the weekend, it appears that e-mail messages created using Microsoft Outlook are most likely to exhibit the pulsating attachment behavior.  For instance, any test encrypted message that I’ve sent from fully-patched installations of Outlook in Office 2003 or 2010 arrive with the pulsating attachment problem on any iPhones and iPads running iOS 7.  When I created similar tests using Mozilla Thunderbird on Linux, two of three recipients received the attachment normally and were able to view it.  Further, any e-mail containing the content attached visibly in-line rather than as a file attachment seems to display fine as well.

So what do we know?  Every S/MIME encrypted message bearing a file attachment and created using Microsoft Outlook from a fully-patched installation of Office 2003 or 2010 exhibits the pulsating attachment problem when viewed on any iOS 7 device.  Encrypted messages with attachments created using Mozilla Thunderbird were readable by some – but not all – recipients using iOS 7 devices.  Encrypted messages sent using Mac Mail on Mac OS typically insert the attachments inline, where the content is viewable without issue.  Long story short, Apple’s Mail App has taken a step backward in iOS 7 where support for encrypted e-mail is concerned.  We can only hope that this is resolved in the next iOS update.

Update:

  • In the first week following this post, it was viewed 374 times from 209 cities in 32 countries.  Readers came from such roles as government (City of Los Angeles, Department of Homeland Security, NASA, and the U.S. Department of Energy), education (Bucknell University, Marquette University, Penn State, UC San Diego and University of California, Irvine) and Apple Inc. offices (Brisbane, Australia; Elk Grove, California; and Zurich).
  • A companion post over at the Apple Support Communities got 615 Views and counting.
  • Apple released iOS 7.0.2 to deal with security issues on the lock screen.  It did not address this problem.

Update 2:

  • Apple released iOS 7.0.3 on October 22nd.  It did not address this problem.

Update 3:

  • Apple released iOS 7.0.4 on November 14th, but did not fix this problem.  Following the upgrade on my iPad, I am not presented PDF attachments at all on S/MIME encrypted messages created via Outlook and sent via Exchange Server or Google-hosted IMAP accounts.  It’s as if they’re not there.  A Microsoft Word .DOC attachment still pulsates rapidly as in the original illustration.  My iPhone, however, shows both file types pulsating.

Update 4:

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Comments

  1. Thanks for the article im having a similar, but slightly different problem with receiving S/MIME attachment emails from Novell Groupwise clients. The attachment box doesnt pulsate, but when clicked it brings up the box to send to air drop or open in dropbox or some other app. Even when clicked open in other apps it still doesnt work at all. This feature worked fine in iOS6 to open MIME Attachments, but with iOS7 I can no longer read my forwarded emails from Groupwise Clients on my phone. I did find a work-around that if you forward that same email again to another email address (of your own) on your phone it will show up and work fine. Strange I know, but still frustrating none the less…

    • I am having the same problem. Were you able to find a solution? Another user with, essentially, the same setup does not have this problem.

      • Robert Parks Robert Parks says:

        Dan,

        If you were directing your question to David and it pertains to GroupWise, I can’t answer that. However, if this is a question on the topic of attachments within S/MIME encrypted messages in general, I’ll mention that I’ve yet to see any solution that works when receiving messages originally created using Outlook. This post has had 1,322 pageviews at the time of this writing, so there are a fair number of us in the same boat.

        Robert

  2. I noticed another strange behavior in iOS 7. It seems that Apple is somehow syncing decrypted messages across devices. Example: I have two idevices – one with installed s/mime certificate and one without. When I receive an encrypted mail (it’s definitely encrypted, tested on Gmail web interface), it gets decrypted I guess on the device with the certificate and somehow synced in decrypted form to the device without certificate because I can read the message there in plain text. Did anyone else spot this behavior? I think that’s really a big security issue!

    Raphael

    • Robert Parks Robert Parks says:

      Raphael,

      That’s not been my experience. For instance, a colleague just replaced his iPhone, but not his iPad, both of which are running iOS 7. We had to reload his certificates on his new iPhone before he could resume reading encrypted e-mail.

      Having said that, your experience warrants further investigation. If there’s any scenario at all where iOS is syncing decrypted message content or the keys themselves with iCloud and your other devices, that would obviously defeat the whole point of end-to-end e-mail encryption. I’d always been concerned about this to the extent that I disabled iCloud backup on my own iOS devices in the same configuration profile that I use to install my certificates. I hope to set up some test scenarios soon to look into your issue further.

      Robert

  3. Omar F. Rodriguez Morales says:

    I made a java backend that runs on AIX and sends encrypted/signed emails with S/MIME with 4 different PDF files, but the ipad and the iphone show all the attached files all alike, the user sees the first pdf file and then when he tries to see the others, the info of the first one is displayed in the second and the third one and so on, on the macbook pro, android, blackberry, windows clients show the attachments properly

  4. Steve Rinsler says:

    Thanks for the effort.
    My problem is appointments sent from Outlook 2010. The first one after resetting the iPhone worked and populated Calendar, no subsequent ones have worked.

    The file names are all mime-attachment.ics, I thought previously they had different names??

  5. CanadaDave says:

    I have found a simple work around. Not sure why it works but it does for me. If I forward that email to myself.(same email account). I am then able to open the attachement(s).

  6. I have a work around based on the fact that MacMail places the images inline. I place a signature or type my sig after the image. So “message-image-sig” This places the image inline so to speak and it views and can be acted upon in Mail. Hopefully this works for others. Sad workaround, but still a First World Problem.

    • Robert Parks Robert Parks says:

      I know you only facetiously suggested that this is a “First World Problem,” but for the record, this blog post has been read by people in the following 79 countries…

      Andorra • Angola • Argentina • Australia • Austria • Belarus • Belgium • Bolivia • Bosnia and Herzegovina • Brazil • Bulgaria • Canada • Chile • China • Colombia • Costa Rica • Croatia • Cyprus • Czech Republic • Denmark • Dominican Republic • Ecuador • Egypt • El Salvador • Estonia • Finland • France • Germany • Greece • Guatemala • Guernsey • Hong Kong • Hungary • Iceland • India • Indonesia • Ireland • Israel • Italy • Japan • Kenya • Kuwait • Latvia • Lithuania • Luxembourg • Malaysia • Malta • Mexico • Morocco • Netherlands • New Zealand • Norway • Pakistan • Paraguay • Peru • Philippines • Poland • Portugal • Puerto Rico • Qatar • Romania • Russia • Saudi Arabia • Singapore • Slovakia • Slovenia • South Africa • South Korea • Spain • Sweden • Switzerland • Taiwan • Thailand • Turkey • Ukraine • United Arab Emirates • United Kingdom • United States • Vietnam

  7. Francisco H. / Mexico says:

    I have the same issue addressed by so many. I own a new Mini iPad Retina, iMac and a MacBook Air but I still have (and happy as ever with it) a Black Berry cell phone. I’ve tried with success an adviced that I found it in this Forum, just re send the email received to your self and bingo! The attachement will be open flawless. But still remains the big question, why this company that Steve Jobs did a great job in achive a friendly face to the Apple universe is doing nothing in such a sensitive problem?

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