File loads into Plex but will not play

Plex Media Server Metadata & Adding Files
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Server Version#: 1.18.0.1913 (running on QNAP)
Player Version#: 4.8.4

I am loading my Hawaii Five-0 (2010) DVD set into Plex. The load works fine and the episodes are added. When I click to play some episodes, like one with the file name:

Hawaii Five-0 - s01e06 - Koʻolauloa (North Shore of Oʻahu).mkv

I just get the spinning circle and the episode never starts. Before I start searching logs, could anyone tell me if there are file name restrictions in Plex? I use Linux on a QNAP NAS.

Thanks

PS; - the same thing happens with file name Lost - s03e14 - Exposé.mkv

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I thought I would post this so that someone may find this useful in the future.

There are certain legitimate file name characters that Plex (on QNAP) will have a problem with. These characters are:

| " ʻ?
Also all the accented characters - i.e. the é in Exposé.

There may be others.

Plex will load these files, identify them and add the metadata to the database but will not play them. Plex puts up the artwork and then the orange circle spins endlessly.

For those linux users I wrote a quick script to change the file names by replacing the problem characters with underscores and print a new filename that is more Plex friendly. I don’t use Windows so please don’t ask for a version that runs on that.

#!/bin/bash
#
FULLNAME="/plex/TV Shows/Hawaii Five-0 (2010)/Season 00/Hawaii Five-0 - s00e0100 - Danny & Steve, Best Buddies + Partners || (2019)?.mkv"

PFF_DIRNAME=$(dirname "${FULLNAME}")/
PFF_BASENAME=$(basename "$FULLNAME")
PFF_FILENAME=${PFF_BASENAME//[^a-zA-Z0-9()_^&%#$@!+, \'.-]/_}


echo "     Original file name = $FULLNAME"
echo Plex friendly file name = ${PFF_DIRNAME}$PFF_FILENAME

The output from this script is:

     Original file name = /plex/TV Shows/Hawaii Five-0 (2010)/Season 00/Hawaii Five-0 - s00e0100 - Danny & Steve, Best Buddies + Partners || (2019)?.mkv
Plex friendly file name = /plex/TV Shows/Hawaii Five-0 (2010)/Season 00/Hawaii Five-0 - s00e0100 - Danny & Steve, Best Buddies + Partners __ (2019)_.mkv
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