WMA Lossless Playback Failure - Windows Media Audio 9.2 Lossless

A large amount of my music collection is ripped from my CDs as WMA Lossless. It seems that Plexamp (or mpd) is failing on a significant number of my tracks. Note that they play through the Plex server web app.

An example file that failed through PlexAmp, but played through the Plexamp has the following metadata from the Web client:

Media Info from Windows Media Player:
wma player info:
929 Kbps
Windows Media Audio 9.2 Lossless
VBR Quality 100, 44 kHz, 2 channel 16 bit 1-pass VBR

Media Info from Plex Web App:
Files
07 Angie.wma 
Media
Duration 4:31 
Bitrate 877 kbps 
Container ASF 
Part
Duration 4:31 
File 07 Angie.wma 
Size 28.43 MB 
Container ASF 
Codec WMALOSSLESS 
Channels Stereo 
Bitrate 1152 kbps 
Album Gain -3.44 
Album Peak 336460390220045549992026835293933928448.000000 
Album Range 9.581674 
Audio Channel Layout stereo 
Gain -0.46 
Loudness -17.54 
Lra 8.21 
Peak 0.998901 
Sampling Rate 44100 Hz 
Stream Identifier 1 
Codec LRC 
Format LRC 
Timed Yes 
Codec TXT 
Format TXT 

The analyzer seems to also have problems too… sometimes able to calculate a waveform and sometime not.

Screencap of it analyzing but not playing audio… (also the analysis is a bit suspicious)

Windows 10, 10.0.16299.0

Moved to question.

Can you DM me a sample file which is exhibiting issues?