This is because currently, the refresh.py Python script re-synchronizes ALL TeamTrack (Business Mashups) items with ALL Perforce Changelists since the inception of the integration. If this integration has been in place, it may be trying to syncrhonize hundreds of thousands of records.
Workarounds: Refrain from using the "Log On as Another User" when testing long redo messages Shorten the Shell.RedoMessage in the script or test with fewer unfilled required fields
After upgrading to 66109, this script will no longer let the user pass on the second run, unless the check box is on the screen and not read only. Once the field is shown during that transition, and not read only, it will work as expected.