Figured out the issue. It actually was an issue I thought I had addressed, but hadn’t fully fixed.
The issue is addressed here.
My button to end the routine was in the same place for back to back routines. I had made it so that one the second routine, the button didn’t start until .5 seconds in, but on the first routine the button was active immediately. That made it “skip” the first routine every other time because I had “clicked” the button.
I now have all buttons starting .5 seconds after the routine begins, and it appears to be working.