We're always seeing customers call in developer support on problems related to their addins often being intermittently soft-disabled.
If you're running Outlook 2007, here is one way to log whats happening inside outlook to aid in your troubleshooting.
You can enable Outlook logging in Outlook 2007 by:
- Go to File… Options…
- Select Other tab
- Click Advanced Options
- Ensure “Enable logging (troubleshooting)” is ticked
- Ok out
Log files are created as .etl files and stored in %userprofile%\Local Settings\Temp. A new log file is created each time Outlook starts. The log file created may or may not help with isolating the issue with the add-in but might give you a better idea of where to look.