Safely Sending files via messaging apps

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As we mentioned recently, one way to safely and securely send Office documents around is to use one of the new messaging apps that are available.

The many apps vary in features and quality.  Any of them have more and better features than standard mobile phone texting.  In fact, these apps are expected to overtake SMS messaging in the near future.

Messaging apps can send images, video, files, receive/read receipts and offer some encryption of the messages.  But not all of them have these features or have them fully implemented.

We’re not going to do yet another broad review of messaging app, there are many of those around.

As befits we’re going to focus on some of the important features for Microsoft Office users.

  • Can the app send documents? Some messaging apps can only send certain types of files like images or video.
  • Is there a desktop version available? Some only work on devices.  Office users will want to send directly from their Windows or Mac computer.
  • Proper privacy and security with ‘end to end’ encryption. This is where most messaging apps let their customers down.  Most have some form of security but there’s gap where your messages and files can be read by others.

Privacy questions have been closely checked by Electronic Frontier Foundation in their Secure Messaging Scorecard (now out of date).   For us, the key question is “Encrypted so the provider can’t read it?”.

To be truly secure, only the sender and receiver should be able to read the message or files.  That might seem like an obvious feature, but you’ll see from the EFF table that it’s the exception not the rule.

Here’s a look at some of the messaging apps according to our criteria.

Only one of the services we’ve looked at gets a perfect score on all points – Telegram in secret mode.

Encrypted so the provider can't read it?Overall Score
(out of 7)*
FaceTime (Apple only)YesYesYes5
iMessages (Apple only)YesYesYes5
Google Hangouts / ChatNoYes (browser)No2
Telegram (Secret Mode)YesYesYes7
WhatsAppNoYes (browser)No2
Yahoo MessengerYesYes (in Yahoo Mail)No1

* The EFF doesn’t give an overall score, we’ve done it to give you a quick idea of how secure and private a particular app is.  Check the EFF site for details on each app.

As you can see, Skype and Yahoo Messenger have very poor privacy and encryption.

WhatsApp is very popular but has very poor security.  A recent German report is scathing about WhatsApp encryption calling it “of little use in the real world”.  Leaving aside all the technical details, the key problem for regular users is that WhatsApp gives you no indication of what encryption (if any) is being used.

At the other end of the scale, Wickr is very secure.  Wickr is so secure that it becomes difficult to use.  Each message has a ‘self destruct’ time limit, after which the message is deleted from both the sender and receivers device.  In practice, people don’t always want that level of security.

In the middle ground is Telegram.  It’s very secure in the secret chat mode but also has a regular mode which is OK for most situations where high security isn’t necessary.  Telegram has Windows, OSX and Linux clients as well as Apple, Android and Windows mobile devices.

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