We enabled the externalrecipient mailtip in our organization however it is not behaving as expected. Users only receive the "external recipient" mailtip if the domain of the recipient is explicitly listed on the remote domains tab. In other words, if we have *.xyzcorp.com listed on our remote domains, the user will receive the mailtip, however an external recipient at hotmail.com will not because we have not explictly entered *.hotmail.com . It's as if it doesn't take into consideration the Default remote domain of * as all other domains. Surely this isn't expected behavior?

Please share the article where you studied mailtips will be enable for remote domains.Best Rgds, Ashish | Unified Comunication | MCTS | MCITP | Please remember to select option "Propose As Answer" if solution work for you | My posts hold no assurances, no promises, and they measured no rights.

http://msexchangeteam.com/archive/2010/01/06/453696.aspx However, the article states that it determines if a recipient is external by means of looking at the accepted domains list in exchange. If the recipient is not listed, it is considered external. However this is not what we are experiencing, we only get the mailtip if the domain is listed on the "remote domains" tab in exchange

I assume that the issue happens on OWA as well, right? You’re right about how the recipients are determined to be external, which is based on the list of accepted domains The external recipient tip are working normally in my lab after enabled the setting and reset the IIS (Exchange 2010 RTM) Get-OrganizationConfig | Fl *Tip* MailTipsExternalRecipientsTipsEnabled : True MailTipsLargeAudienceThreshold : 25 MailTipsMailboxSourcedTipsEnabled : True MailTipsGroupMetricsEnabled : True MailTipsAllTipsEnabled : True Please check the outlook diagnostic log files which will record the MailTip requests and response How to enable diagnostic logging: Click “File” button, “Advanced”, select “Enable troubleshooting logging (requires restarting Outlook)”, restart outlook The log files location: %LocalAppData%\Local\Temp\Outlook Logging Notes: To make the log more readable, copy the log to word, and then replace all “><" with “>^p<”, which will add returns between lines Please check the settings of /EWS virtual directory on CAS server Default settings for Exchange-related virtual directories in Exchange Server 2010Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.