Bad_Stale timestamp on one tag but not the other in Transaction Group

I have two tags:

Both are basic memory boolean tags and in the same tag provider.
If I use the first one as a trigger in my transaction group, it triggers just fine and this expression gets the timestamp just fine and values are written to the database.

If I use the second tag as the trigger, I see the value change to true, but the timestamp on the expression item continues to say Bad_Stale:
image

I am not sure where to look for anything that would cause the second to not work. The Gateway logs do not show any errors. There is nothing in the Transaction Group Designer that is shouting at me. And I made sure to change the Execute on trigger to the tag I was testing.