Got it again today, on "Little Ed" again. This time with cutlass. As I was getting the heal, an assassin got my pirate - pirate woke up in jail with health ABOVE the groggy bar and the healing dialog persistent.
Was able to run through to other places, e.g. El Sudoron...
Unlike last time, this time limited the heals I could do to one. So I still have to figure out the other one (where I had as many as I wanted) with the dagger, but not going "to jail."