Occasionally it is necessary to resolve problems by turning on the debug log file. You can then examine this file yourself to see if there's anything obvious going wrong.
In particular, you can search for the words "Error occurred". Sperry Software always prefaces errors with these keywords to make it easy to search for and find potential trouble spots.
To turn on the debug log file:
Go to (in Outlook) the Sperry Software tab
Click on the red/blue gear icon to pull up the Configuration window
Click on the Options button (in the lower left)
Check the box that says "Enable writing to the log file"
Take note of where the log file will be written, you will need this later (it's always named "SperrySoftwareLog.txt")
Click Ok, then Ok again to get back to the main Outlook window
Reproduce the problem
Now, go to the folder where the log was written and open it (you can use Notepad, it's just a text file)
Search for the words "Error occurred" and take action (or send it to us)
Note that if you cannot find the log file that you can always go back to the Configuration window, back to the Options button, and just to the right of the "Enable writing to the log file" checkbox is a button that says "Send to Support". This pulls up a pre-addressed email with the log file as an attachment. You can open it and examine it from there (you don't necessarily have to send it to us).