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.
- 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.
- Apple released iOS 7.0.3 on October 22nd. It did not address this problem.
- 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.
- Apple released iOS 7.1 on March 10th, 2014. It seems to resolve the problem.