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tmux control mode (often) fails to launch window when creating or attaching to a session

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Detailed steps to reproduce the problem:

  1. SSH to a raspberry pi 4 on my local network (with tmux 3.3a-3 Debian package installed).
  2. Attempt to launch tmux control mode via tmux -CC new -A -s main.

What happened:

Sometimes this works (~50% of the time) and the tmux window launches and sometimes it doesn't and I'm just stuck with the "** tmux mode started **" and Command Menu in the original SSH window but no tmux window launches (the tmux dashboard is empty and unresponsive as well). I try esc and X to detach, but the original SSH window seems borked, so I close it and start over again.

What should have happened: The tmux window launches 100% of the time on all the other remote servers that I SSH to (including servers running tmux 2.6 and 3.3).

I'm not really sure how to debug this as I've tried various config option changes and done extensive Googling, and I'm still stuck. Any help would be greatly appreciated. I have developed various superstitions about how to control the probability of it happening, but I think they're all wrong. ;)

Edited by Eric Battenberg