Library Shuffle Won't Play Anything (Error:Could not start playback. There are no playable items.)

To clarify, suppose I have the following setup:

TV Shows > Seinfeld
TV Shows > Friends

Selecting Shuffle in TV Shows brings up the error:

Could not start playback. There are no playable items.

But selecting Shuffle in Seinfeld seems to work fine.

Thoughts?

Plex

Version 3.27.1

Player

Model: 4200X - Roku 3
Software Version: 8.0.0 = build 4143-04

PC

Operating System: Windows 10 Home 64-bit
CPU: Intel Core 2 Duo E7400 @ 2.80GHz Wolfdale 45nm Technology
RAM: 6.00GB Dual-Channel DDR2 @ 398MHz (6-6-6-18)
Motherboard: Dell Inc. 0T287N (Socket 775)
Graphics: 1024MB NVIDIA GeForce 8400GS (EVGA)
Storage: 698GB Western Digital WDC WD7501AALS-75J7B0 ATA Device (SATA)
Optical Drives: TSSTcorp DVD±RW TS-H653G ATA Device
Audio: NVIDIA High Definition Audio

Same here with JPEG or MOV files. logs enclosed.