To correct my previous comment 
(https://bugs.launchpad.net/ubuntu/+source/pidgin/+bug/302314/comments/3), the 
path to place the login.live.com certificate (or any other certificate you want 
Pidgin to accept per-user) is 
~/.purple/certificates/x509/tls_peers/

Sorry for the confusion. I was thinking of /etc/ssl/certs instead. You
probably don't want to just dump certificates in there.

To emphasize, making symlinks in your home directory or dumping trusted
certificates in ~/.purple are just crude short-term workarounds to avoid
accepting untrusted certificates because of a bug. They aren't long-term
solutions.

komputes: I haven't had any issues with rsi.hotmail.com, though
according to http://developer.pidgin.im/ticket/6680 you might have
offline messages that aren't getting through. Apparently MSN uses a
different host and a different certificate for offline messages. Until
an official fix for Ubuntu is released you could perform the Firefox
workaround I suggested above for login.live.com with rsi.hotmail.com, or
you could find another way to verify the certificate (there are some
instructions on using openssl and a certificate in the Pidgin ticket; it
appears to be out of date though), or you could just accept the
certificate if you're feeling lucky (though I wouldn't recommend it).

-- 
Pidgin not using existing root TLS/SSL certificates for validation
https://bugs.launchpad.net/bugs/302314
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