Craig... yes, that looks like similar to what I am doing and what I described that's causing the problem.
"Always stream audio through effects..." is on. Changing the tail length setting to 10 seconds didn't do anything.
Stretching the tail of a short clip does not fix the problem. However, just to check... I set up a long clip on a 2nd track with a send to the reverb bus, so that it starts just before the 1st clip ends, then turned down the 2nd track to barely audible... and the reverb tail works for the first track... I'm guessing since audio continues to stream into the bus from the 2nd track.
However, that doesn't explain why putting a short or no decay effect before and after the reverb causes the problem in any case, and removing either of those short decay effects, the reverb tail plays fine.
I've reproduced the problem on my system using quite a few different plug-ins, including a long repeat delay... the delay also stops outputting once the input to the bus stops.
The CWB file I sent to Cakewalk that has the problem on my system, has a bus containing Channel Tools > Breverb 2 Cakewalk > Boost 11.
The bus stops output when either (1) the short audio WAV file ends on the track, or (2) on a long track... say, just after a snare hit... the bus send is automated to go to zero output... the bus output audio stops as soon as the bus send track automation goes to zero output.
Quite annoying, when you've been working on multiple projects, that are fairly busy... and you've thought for a while (weeks) things weren't sounding right... and just now realize... it's because some of the reverb/delay buses are no longer working correctly. And I really have no idea when exactly it started happening. Maybe when Aux Tracks and Patch Points were introduced? Or maybe earlier even. No idea, really.