Error Messages: When they could be more helpful...

The last few weeks I've been tripped up by this odd issue with connecting calendars in SharePoint to Outlook 2007. The problem was following me from machine to machine, which made it particularly troublesome. Other people I tested with could properly connect to the calendars, so I knew it wasn't a show-stopper for our SharePoint (WSS 3.0) roll out, but I knew I'd need to get it solved at some point.

The only two symptoms I had that seemed worth any salt was the fact that the "sharepoint.pst" file wasn't being created and Outlook would throw an Informational Event in the Application log, that stated "Operation Failed" (Event 27). So which operation was failing?

Turns out we had an odd collection of things going on that contributed:

1. An Office GPO set a while back during our Office 2007 deployment defaulted newly created PST files to sub-folder in the user's home folder called "outlook" (Ex. home\outlook)
2. Several users (including myself) had an unexplained file named "outlook" (no extension) of 265MB in size in their home folders.
3. Users (like me) who didn't use PST files or had their PST files in a different location before the policy was applied.
   

The GPO policy wouldn't have been an issue, if not for the random "outlook" file that was blocking the creation of the sub-folder for the sharepoint.pst placement. (Bad default PST file creation after the software upgrade from Office 2003? Failed personal mailbox creation if the server/username couldn't be resolved for some reason?)

The Windows operating system will allow the creation of folders that match filenames as long as the file has a file type extension on it, but if the file doesn't have an extension it's not possible to create a folder of the same name. If this problem occurs in Windows Explorer, an error message will pop up.

However when Outlook 2007 was confronted with the inability to create the sub-folder, it failed in a mostly silent fashion - providing only the "operation failed" message, without any additional information that would have been valuable in the moment. A error window or line in that application log error detailing the path to where the sharepoint.pst file was supposed to go would have made the error quick and easy to resolve.