In my post last week about Office 365 and proxy servers, I mentioned issues with Outlook autodiscover.  These were not exactly easy to troubleshoot, often with multiple subject matter experts looking from different angles (network, client applications, Exchange, firewalls, etc.). During the process, we used a few tools (as well as examining the traffic hitting the proxy servers) and I thought I’d highlight them here (if only for my own future reference):

• The obvious starting point is the Outlook Autodiscover tests on the Microsoft Remote Connectivity Analyzer (RCA). I was using the Office 365 version but one of the other SMEs working on the issues suggested that the Exchange version is a better test as it doesn’t have hard coded addresses in it – your mileage my vary.
• Next up are some handy tests built into Outlook: Ctrl+right click on the Outlook icon in the task bar and you’ll see various tools including Connection Status and Test Email Auto-Configuration. I’ve written about these before… although they’re worth mentioning again!
• Outlook logging is another option (although it doesn’t create the olkdisc.log file in Outlook 2013). More details are in Microsoft knowledge base article 2862843.
• Kip Ng’s standalone autodiscover test tool (autodiscovertest.exe) is very useful when you can’t get network access to the RCA. Michel de Rooij summarises it in his post and there’s more information in Kip’s post.
• Finally, EWS Editor is a useful tool for testing Exchange Web Services, including troubleshooting Autodiscover.