Transition for linked task not working when second linked task exists

[Clara June Nicolay]

I am having an issue where a linked task isn't transitioning automatically in a specific situation.

I have two projects and they frequently automatically transition linked tickets (projects or for support and developers).

Situation #1: In the event that a support task creates a only developer task (dev task is 'cloned by' support task), all my transitions work properly

Situation #2: In the event that a support task creates a developer quote (dev task is 'required' to support task), then once that task transitions, the support task creates a developer task (exact same button/transition as situation #1) suddenly none of my transitions work any more.

I can provide more information if this isn't enough but that is my broad issue. I have no idea why these transitions wouldn't work as they are pretty out-of-the-box.

Thanks for any help anyone can provide!