I have a scheduled task on my Windows 10 machine and some days I observed that it did not run. Once it missed the run, it would not run forever till I manually kick off the job again. On internet, I could not find the answer so after trial and error, I found that the task had a condition “Start the task only if the computer is on AC power”. It seems like when the last time the task about to run, my machine was not on AC and hence task could not start. As soon as I removed this condition, it started working. I don’t know why after one missed run, it would not run again but at least it solved my problem.