I've been working for a number of days to resolve a problem that appears to be a sharepoint/outlook bug and I'm writing this to confirm my findings against your experiences/knowledge.
I've an approval workflow with "Reassignment" checked off. When the workflow fires off, it emails the assignee a task. Assignee opens the message and clicks on "Open this task...".
Reassignments don't work quite right.
If you want to reassign a task from an outlook mail message, you click the "reassign task" button and you are presented with a form asking you to specify the reassignee via a people picker. This people picker simply doesn't work (putting usernames
in and pressing enter does no validation and actually creates a new line in the people picker). The icons to the right of the people picker do nothing.
If you provide user data, sometimes the reassignment gets sent, sometimes it simply completes the workflow as rejected.
Again, this only happens handing approval reassignments from outlook. If you navigate to the actual task in sharepoint, everything works as expected.