This is an unordered list of tools and functionality that is handy when troubleshooting Outlook Anywhere or Outlook RPC-over-HTTPS as it was previously known.

• Wireshark
  Excellent network protocol analyzer, use it to see what Outlook and Exchange send over the wire. It is possible to configure Wireshark to decrypt an SSL stream, I will post a how-to about this soon.
• Outlook Debug Logging
  Enable from ToolsàOptionsàOtheràAdvanced Options…àEnable logging (troubleshooting)
  This will generate log files in the user’s temp folder as well as events in the Event Log.
• Outlook Connection Status/Test E-Mail AutoConfiguration…
  Access by right clicking the Outlook icon in the system tray/notification area while pressing CTRL.
  In the Connection Status window you can see server names, connection types, network interface, protocols, status and statistics. Also you can view the activity in your local mailbox. The Test E-Mail AutoConfiguration option shows you all the information delivered by the Autodiscover web service.
• Outlook RPC diag
  Start Outlook with the command line parameter /rpcdiag, eg. outlook.exe /rpcdiag. This brings up the Connection Status box.
• IIS Log files
  Usually located in your inetpub directory these files show you the requests that you web server receives, as well as the return codes the server responded with.
• Windows Event Logs
  Look here for errors from the web server or Outlook, or any other component associated with Outlook Anywhere functionality.
• Test-OutlookWebServices cmdlet
  This cmdlet runs a test on the Autodiscovery web service and outputs the results.

Morgan