Skype is showing the wrong last messages
I use Skype for Mac (as I presume you do), and I've had to troubleshoot contact status issues. In my notes are the following comments with respect to keeping a "detailed log:"


Type in any chat line:
/setupkey *Lib/LogLevel 4
Then quit and restart Skype.
Then type in chat line:
/resynccontacts


Other commands:

/resynclivecontacts

So you probably don't need the detailed session log, but try the resync commands.

For a more advanced method, here is another procedure from my notes:


Quit Skype completely
Access https://m.hotmail.com in any browser
You should see a "403" error page
Restart Skype and verify the contacts are loading


Does that help? I'm sorry that I can't elaborate on the commands and techniques, since these were methods that I found without supporting explanation.