Hey @rubmuncher!
Given there’s at least one timer that’s working, it suggests that this is an issue caused by a human.
Note that if you have too many timers supposed to go at the same time, Nightbot will limit the amount of timers going out in order to prevent spam.
One solution could be to use staggered timers, though using the Quote API will introduce limitations, if it stops working you’ll likely have to clear your quotes list. The other solution, which I think is better because it doesn’t rely on the Quote API, is messages sent at specific stream uptimes, it requires a bit of work to adapt the code to fit your needs, but it’s doable; if you’re interested in this solution but can’t figure out how to adapt the code, let me know, I’ll work on it when I have a minute. Shifted timers might also interest you.
If none of those suggestions fit your needs, maybe what you’re looking for is the Multiple Messages API that allows you to send multiple messages in a short amount of time.
Next, a lot of people having issues with timers often haven’t read and taken the time to understand those two indications when they set up a timer, so I suggest paying attention to it: