Self-hosted runner stuck on "Waiting for a runner to pick up this job..." in multi-step jobs

Describe the bug
Using a self-hosted runner.
When a GitHub action has multiple steps the first will run successfully but then the subsequent step is stuck in queued status with a logging message "Waiting for a runner to pick up this job..."

I am able to get the stuck jobs to start by either cancelling and re-running the job via the GitHub UI or by restarting the GitHub Runner service within our EC2. In both instances the job immediately picks up and runs successfully.

To Reproduce
Steps to reproduce the behavior:

1. Use self-hosted GitHub Runner
2. Use a multi-step action
3. Initiate the action
4. Observe that the 2nd step is stuck in queued status.

Expected behavior
The runner should pick up the 2nd (and following steps)

Runner Version and Platform

v2.321.0 Windowsx64

We noticed that our machine auto-updated with this version on November 27 and then our CI runs the following week started to have this problem.

OS of the machine running the runner?
Windows

What's not working?

"Waiting for a runner to pick up this job..." for up to hours.

Job Log Output

N/A the runner does not get to job output, it is stuck in queue.

No source file or test is named. Reproduce a multi-step job on a Windows x64 self-hosted runner running v2.321.0, then compare the queued second step with the recovery seen after cancelling and rerunning the job or restarting the runner service; done means subsequent steps are picked up without manual recovery.