Does homekit have a cooldown for contact sensor automations?

I've been attempting to troubleshoot (with little success) why my automations for door contact sensors will work once, but not a second time (until some unknown amount of time passes).

I've done a good bit of troubleshooting to rule out obvious things like wifi/network connectivity and issues with the sensor itself. I can verify in homekit that even though the contact sensor is changing its status (proving homekit knows the status changed and in fact should be triggering the automation) however the automation just does not trigger. Its quite confounding.

I also cannot find any mention of a contact sensor cooldown, although this is the only thing that makes sense, beyond a bug with homekit itself (which i cannot rule out).