Older films will direct play, but wont transcode



Hello all, Im running through my plex server testing all of the old disney movies ive acquired over the years and it seems that none of the older ones will play unless I set direct play to "Force"

I dont recall this being an issue until my last plex disaster where I had to reinstall on my FreeNAS box, but I havent had any recent issues with movies lately and I add pretty regularily.

I know the version is pretty old, however I dont like fixing what isnt broken, and would like to try to get this working correctly before I just start from scratch.

Here are my logs: https://drive.google.com/open?id=1_ZL-nIf0yay0xrz1t4nQS6EkjMJFBI-a
Last movie played with errors was "Aladdin"

Plex Server streaming to a Roku 3
Pentium G3240
X10SLM+-F - Factory loaded V2 BIOS
16GB Crucial Unbuffered ECC DDR3 1600 - 1333 mode
2x WD Blue 1TB + 4x WD Red 1TB RaidZ2
Seasonic G series 360W
FreeNAS 11 Stable