Hi @Tyson Chavarie,
I have the same problem with some of my flows. Every day or two, one of them is suddenly stuck in a pending state. Without any action on my side, this one and the following ones in the pool will never be executed.
The only solution I've found so far is to use automation and cancel it if it's in pending state for more than 3 minutes.
I still haven't found the root cause of this problem.
Do you have any information on this issue?