

Don't send confidential messages just before Skype crashes - Terretta
http://heartbeat.skype.com/2012/07/imchat_issue.html

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Terretta
If Skype crashes just after you send an IM, your IM may get sent to a
different user when you restart Skype.

"The Skype clients impacted include: Skype 5.9 and 5.10 for Windows, Skype 5.8
for Mac, Skype 4.0 for Linux, Skype 1.2 for Windows Phone, Skype 2.8 for
Android, Skype 4.0 for iOS."

How to know Skype is about to crash, so you don't say anything you'd rather
not misdirect, is an exercise left to the user.

