Two different servers, same agents, different results

I have two Plex Servers. A private, local network only server and a slightly more public one for family. The content is identical in that the file store for server two is a direct copy, updated everynight, of server one. Same folder structure, same content, same filenames everything. Server Two exists mostly for me to play with as its only using a backup datastore

Server One is Windows Server 1.14.0.1340-0acc754c
Server Two is a FreeNAS Jail so BSD 1.20.3.3483

I have been through the agent settings and they seem identical.

I have a bunch of TV Series.I also have a few movies - but all these are correct

On Server One the posters are all correct for each series
On Server Two most are correct, but not all.
I have removed the series, done the dance and put them back - no effect
I even removed all the series and then did the dance and put them all back. The same set of series fail to get posters, whilst the rest do get posters. Running a match produces a correct match but updating the metadata still doesn’t produce a poster.

I am confused. I could manually add the posters but that kinda defeats the object and would be far too simple a solution.

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