Outlook 2010 includes some great, though rather less than obvious, troubleshooting capabilities. You can enable diagnostic logging from within advanced options of Outlook, and hidden within the application’s system tray icon is the option to test email auto-configuration as well as to determine what messages are displayed to the user.

Enabling this logging, and testing connections, are both great ways to diagnose connection issues and to determine whether any connection problems are on the client side, or the server side. If you’d like to learn more, please read on.

Enabling diagnostic logging cranks up the data generated by Outlook to 11, so it is not the sort of thing we want to just do and leave turned on. If you have a client with connection issues, it is the best way to generate detailed logs of what is going on between the client and the server. When this logging is enabled, Outlook will display a message in the title bar, and lots of disk activity will occur.Here’s how to proceed. One last time, remember…don’t do this just for kicks. It will generate potentially large files, and can also create a performance hit on the client. When you need to troubleshoot the client, turn it on. When you are done…turn it off! Here’s how to turn it on. And notice, this does not require any cryptic registry keys!

1. Launch Outlook 2010
2. Click File, Options.
3. Click Advanced.
4. Scroll down to Other, and check the box to enable troubleshooting logging.
5. Restart Outlook.

To turn it off, simply go back and clear the checkbox, then restart Outlook again.

With logging enabled, a pop up will appear in the system tray reminding you that Outlook logging is enabled.

Once enabled, several log files are generated. Most of them are found in c:usersusernameAppDataLocalTempOutlook Logging. Logging will include details for MAPI, SMTP, IMAP, and POP3 connections in cleartext. Logs will also be generated for all activities that involve the calendar, however these are stored in a binary format that requires MSFT support to use. If you are troubleshooting Free/Busy issues, you can find those logs in %temp%OLKAS, which are fortunately in cleartext format.

With logging enabled, you can diagnose individual connection issues, but the client also has a hidden test mechanism built in to it. You can diagnose the AutoConfiguration settings that Outlook will pick up from Exchange Web Services using the Autodiscover URL. Once logging is enabled, here is how to launch the connection testing that is built into Outlook 2010.

1. Hold down the CTRL key and right-click the Outlook icon in the system tray.
2. Click Test E-mail AutoConfiguration…

This will generate a pop up dialog box that can provide insight into connection errors, name resolution errors, certificate issues, and more.

If you are working on a larger issue that affects multiple clients, keep in mind that you can push settings out using a group policy and the Office Customization Tool. The Outlk14.adm file can be used to configure logging with a Group Policy Object that will save you from having to visit individual machines. Apply it to an Organizational Unit, and consider filtering the application of the GPO using a security group to affect just a subset of the user population. Just always keep in mind that this diagnostic logging can impact client performance, so use this with care, and remember to disable logging when you have the information you need.