Desktop Manager quits in the middle of sync

Desktop Manager just quits in the middle of a sync. I've isolated the offending application to calendar sync with MS Outlook. No warnings, no errors, Desktop Manager just stops running. I tried upgrading to the latest version of Desktop Manager 5.0.1.28, no change. I've tried deleting the Intellisync directory and the problem just reappears after recreating the sync settings.
Bold 9700
Windows XP
MS Outlook 2007

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