Assuming that my inferences are correct:
In the good call, 0 was pressed 5 seconds into the announcement.
In the bad call, 0 was pressed (both times) after the announcement (which I believe is ~12 seconds long) ended. Of course, that shouldn’t matter but it seems that the dial plan code is either messed up or being executed wrong.
First, though your symptoms are very different, confirm that you don’t have one of the ‘bad’ Asterisk versions:
Next, see if you can replicate the problem by pressing 0 after the announcement is over.
If so, see if updating the IVR module helps. If not, adding a few seconds of silence to the end of the announcement may be a workaround, until we can find out what’s wrong.
If you still have trouble, please post a screenshot of your IVR settings, and the contents of the ivr-2 context.