*curses at SWD at a frequency that somehow fails to transmit over a wire longer than 3cm*

Does anyone have any hints on how to extend SWD? Maybe Dsub just fails or wire shielding is a must?
I have not jet looked at it with a scope (too tired), but that will be the first thing to try tomorrow.
I tried a lot already and the board is still alive, this is just the last photo while trying to get any signal ^^

Found a much "better" solution, just extend the USB connection! It works surprisingly well. I'm almost tempted to install a USB hub and USB uart as well or even a Raspberry Pi Zero. But the current plan still allows using the uart or gpios for other things.
@TilCreator My respect you are doing all this.

@TilCreator 3m already sounds like quite a distance.

Maybe try shielding. Maybe even twisted pairs?

@NafiTheBear I already tried shielding without success and twisted pair should only help for signals made for twisted pair (like Ethernet)