Output stops playout from file that did run once ok

Hi together,
I’m on a huge Problem here and i have no clue how and what to do here.
Our Libretime is getting 4 Blocks of Audio (2 x 1h / 2 x 2h) via a Podcast that my external Recorder records from our main Program (FM Radio Station here).

It Plays those just fine but sometimes it plays a specific File (at least the file for that particular hour) just once ok, the second time i then run into this:

2021/10/25 06:00:00 [s4:3] Finished with "/var/tmp/airtime/pypo/cache/scheduler/2858.mp3".
2021/10/25 06:00:00 [cue_cut_7721:3] Cueing out...
2021/10/25 06:00:00 [amplify_7725:3] End of the current overriding.
2021/10/25 06:00:00 [cross_7728:3] No next track ready yet.
2021/10/25 06:00:00 [dummy(dot)3:3] Source failed (no more tracks) stopping output...
2021/10/25 06:00:00 [dummy(dot)4:3] Source failed (no more tracks) stopping output...
2021/10/25 06:00:00 [fade_in_46786:3] Warning: #get called when not #is_ready! This is normal if an operator using this source has been unused while the source has gone unavailable. If unsure about this warning, you are very welcome to report it and ask for clarifications.
2021/10/25 06:00:00 [schedule_noise_switch:3] Switch to map_metadata_7800 with forgetful transition.
2021/10/25 06:00:00 [lang:3] transition called...
2021/10/25 06:00:00 [server:3] New client: 127.0.0.1.
2021/10/25 06:00:00 [lang:3] streams.live_dj_stop
2021/10/25 06:00:00 [server:3] Client 127.0.0.1 disconnected.
2021/10/25 06:00:00 [server:3] New client: 127.0.0.1.
2021/10/25 06:00:00 [decoder:3] Method "MAD" accepted "/var/tmp/airtime/pypo/cache/scheduler/2859.mp3".
2021/10/25 06:00:00 [lang:3] vars.show_name
2021/10/25 06:00:00 [server:3] Client 127.0.0.1 disconnected.
2021/10/25 06:00:00 [decoder:2] Decoder "MAD" betrayed us on "/var/tmp/airtime/pypo/cache/scheduler/2859.mp3"!
2021/10/25 06:00:00 [s4:3] Prepared "/var/tmp/airtime/pypo/cache/scheduler/2859.mp3" (RID 0).
2021/10/25 06:00:00 [s4:3] Finished with "/var/tmp/airtime/pypo/cache/scheduler/2859.mp3".
2021/10/25 06:00:00 [cue_cut_7721:3] End of track before cue-out point.
2021/10/25 06:00:00 [amplify_7725:3] Overriding amplification: 2.020691.
2021/10/25 06:00:00 [amplify_7725:3] End of the current overriding.
2021/10/25 06:00:00 [lang:3] timeout --signal=KILL 45 pyponotify --media-id=7553 &
2021/10/25 06:00:00 [dummy(dot)3:3] Source failed (no more tracks) stopping output...

The problem file here played 6 hours ago without any problems but right at 6 in the morning it does not.

I’m confused since this happens on random days but every time at 6am just when one file ends and a new show begins.
Help is much appreciated !

EDIT:
Before i forget: Downloading the file and Re-Uploading it fixes this problem…

Greetings from Germany

What version of LibreTime are you using ? A lot of changes were introduced recently such as the new API implementation in Python and there were a fair amount of bugs related to scheduling with pypo. Some of which have been fixed. But there were also bugs that were undiagnosed in older versions too. So without knowing either the release or git commit # it’s hard to say what could be the cause of this problem.

So when running the install script i used back then is says:
LibreTime Version 2003e685b

Seems like there has been a Mayor Upgrade since then, i’m a Bit afraid of doing this since LibreTime is Air-Critical in our System.
Could i upgrade to the newest release in Github or should i go version by version ?