There may be something wrong with assigning events to timers, but that can't
explain why the second timer didn't record anything.
Are there no log entries regarding the second timer?
My wife programmed two recordings on "Das Erste" about 'Die Französische
Revolution'. At least the second one (I didn't yet dig for the older
logs) appeared at every restart with the entry "timer x set to ..." but
when the time to record came, nothing happened. VPS was switched off.
The log contained only the "timer x set to" and the "channel 1 .....
status 4" message, when the xmission started. There where no other
recordings running at that time.