Recordings not deleting

I have a series pass setup to only keep the latest 1 recording. A lot of the times, the old recording is deleted, but sometimes it does not delete. A sample from the log this evening is below. It should have deleted the previous episode of this series.

2018/07/21 17:59:26 [NAT] Successfully mapped port 8089 using upnp
2018/07/21 18:29:47 [DVR] Waiting 2.010572849s until next job 1532212190-1 NBC Nightly News With Lester Holt
2018/07/21 18:29:50 [DVR] Starting job 1532212190-1 NBC Nightly News With Lester Holt on ch=[36.1]
2018/07/21 18:29:50 [TNR] Opened connection to 10432322 for ch36.1
2018/07/21 18:29:50 [DVR] Recording for job 1532212190-1 from 10432322 ch36.1 into “TV/NBC Nightly News With Lester Holt/NBC Nightly News With Lester Holt 2018-07-21 2018-07-21-1829.mpg” for 30m9.992129976s
2018/07/21 18:59:26 [NAT] Successfully mapped port 8089 using upnp
2018/07/21 19:00:00 [TNR] Closed connection to 10432322 for ch36.1
2018/07/21 19:00:00 [DVR] Finished job 1532212190-1 NBC Nightly News With Lester Holt
2018/07/21 19:00:00 [DVR] Waiting 23h29m49.677333541s until next job 1532298590-1 NBC Nightly News With Lester Holt
2018/07/21 19:00:00 [DVR] Processing file-123: TV/NBC Nightly News With Lester Holt/NBC Nightly News With Lester Holt 2018-07-21 2018-07-21-1829.mpg
2018/07/21 19:00:02 [DVR] Running commercial detection on file 123 (TV/NBC Nightly News With Lester Holt/NBC Nightly News With Lester Holt 2018-07-21 2018-07-21-1829.mpg)
2018/07/21 19:06:33 [DVR] Commercial detection finished with 8 markers.