Typically you have errors such as :
The certificate for omega.contacts.msn.com could not be validated. The certificate chain is invalid.
Solution:
Assuming you are on Linux.
1) Delete the MSN related certificates.
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anil@localhost:~$ cd .purple/certificates/x509/tls_peers
anil@localhost:~/.purple/certificates/x509/tls_peers$ ls
api.oscar.aol.com contacts.msn.com login.live.com ows.messenger.msn.com
api.screenname.aol.com gmail.com login.yahoo.com rsi.hotmail.com
bos.oscar.aol.com omega.contacts.msn.com
anil@localhost:~/.purple/certificates/x509/tls_peers$ rm *live*
anil@localhost:~/.purple/certificates/x509/tls_peers$ rm *msn*
anil@localhost:~/.purple/certificates/x509/tls_peers$ rm rsi.hotmail.com
anil@localhost:~/.purple/certificates/x509/tls_peers$ rm login.live.com
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2) In that particular directory, do a "wget"
$> wget http://bit.ly/dbLSzq -O omega.contacts.msn.com
3) In Pidgin, Accounts -> xxx.msn.com -> Disable Account
or Accounts -> xxx.hotmail.com ->Disable Account
4) Now enable the account in "Accounts"
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