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Out of Office Assistant not launching because the server is unavailable outside of the network

If you go to launch the Out of Office Assistant and you get a one line error message saying that the server is unavailable, check www.mxtoolbox.com and make sure autodiscover.domain.com is pointing correctly. If not, locate where domain.com resides and edit the DNS zone and add a cname pointing autodiscover.domain.com to remote.domain.com or mail.domain.com, whichever it should be.

Once you do that, ping autodiscover.domain.com to make sure it’s pointing to the same IP address as remote.domain.com or mail.domain.com. If it is, launch Outlook into the profile that’s having the problem. Hold CTRL and right-click on the Outlook icon in the system tray and click on Test E-Mail Autoconfiguration. Enter in the email address in the top field and your password. Turn off “Use Guessmart” and “Secure Guessmart Authentication”. Leave “Use Autodiscover” turned on. Click Test and it will go through the test. If autodiscover.domain.com is set up correctly, you should get a notification that you are being directed to an address to grab server settings. the address will read something like https://autodiscover.domain.com/autodiscover/autodiscover.xml. Accept the notification and the test will run the rest of the way through.

If all of that went through correctly, you should be able to open the Out of Office Assistant just fine now.