Sometimes, problems with the SSL certificate are responsible for broken emoticons on the desktop client as opposed to the web client. Native clients are very strict when validating the certificate chains.
Are you running the Server or Data Center version of Hipchat? If that is the case, please check with your system administrator whether the certificate chain for Hipchat is complete (i.e., including root and intermediate certificates).
If you're unable to make progress, please feel free to contact our support team for troubleshooting assistance.
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...able to use the clients After a bunch of testing (rooms, memberships, check for private message history, and most importantly - the custom emoticons!) nearly everything was looking as we needed, however...
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