[Bug] Chisel is behaving differently if ran from cmd and powershell than git bash

I am having behavior differences in the bash I choose to run chisel.

My setup:

Client:

OS - windows 10.
SSH-agent - vscode-remote,
TCP tunnel - Chisel.

Server:

OS - Debian 10 (in a docker container)
SSh-server - dropbear
TCP tunnel - Chisel.

To summarise: vscode-remote (ssh-agent) -> chisel (client) -> chisel(server) -> ssh server

My senario:

When vscode-remote has a run time error it opens a new connection to the ssh server (chisel tunnel in this case) waits for the new connection to be opened and reroutes the session through the new connection keeping the old with the new.

I have a scenario in which I can make vscode-server throw a run time error and I can see in netstat that indeed a second connection is opened, but here our paths diverge.
If Chisel (client) is run from git bash (MINGW64) vscode-remote receives a signal from Chisel that the new connection is open but if Chisel (client) is run from PowerShell or CMD vscode-remote doesn't receive this signal and loses the connection.

In both cases, I am running a .exe binary version compatible with windows amd64.

I want to understand what can cause this strange behavior and what is the contract between the ssh-agent and chisel regarding the connection life-cycle.

No source files, tests, or entry points are named. Start by reproducing the same Windows amd64 client and tunnel through Git Bash, PowerShell, and CMD, then compare the connection lifecycle and signal behavior; done means identifying the cause and documenting the ssh-agent/Chisel contract or a narrowly scoped fix.