When we're using the Transfer Owners action in a list view, it's not firing triggers marked with After Update flags. I initially suspected it was because I was only running the trigger if the update was made on a specific field so I changed it to any update and it still failed to run. Right now we're having to go in and manually fire the trigger whenever we use the Transfer Owners function.
I don't think Transfer Ownership is supposed to run triggers.
If you wish to run triggers you can do so separately.
Even if my trigger is tied to who owns the record? This is something the specifically runs when ownership changes so it's important that the triggers work afterward.
Would it be possible to put an option on the transfer ownership screen to run or not run related triggers?
I'll put this in a queue as an enhancement.