My apologies for getting back to this bug after a long time. Here is
what I've to share that I had come across some months back but could not
find enough time to report it here (glad I'm doing it now). Though I
have reported it on ubuntuforums.

Here it is:

If I start the skype with super user privileges, it works perfectly.
Strangely enough the application interface also gets a bit changed. More
sharp and sleazy. Moreover, the file sending also gets underway smoothly
no matter how big the size. But again if I run skype without "su" the
"file send crash problem" arises.

I've also tried to do some work on file like for wireshark to capture
and display packets we have to

sudo chgrp XXXXX /usr/bin/dumpcap  
sudo chmod 754 /usr/bin/dumpcap
sudo setcap 'CAP_NET_RAW+eip CAP_NET_ADMIN+eip' /usr/bin/dumpcap

Don't know what to do in case of Skype

Hope this might be helpful towards diagnosis of the problem.

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https://bugs.launchpad.net/bugs/1069618

Title:
  Skype App crashes when sending files

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