Easily reproducible here. Take the EN_US 1803 image (MLF_X21-79647.ISO) and create a virtual vanilla Windows from it. Select Danish for Time, Currency and Keyboard. Then Windows 10 Enterprise. And finally Denmark as region and keyboard once more. Install VMware Tools (or whatever is needed for your virtualbox). Apply all updates from Windows Update. When windows have finished updating, install tcmd-22.00.42.exe and create a shortcut for TCC on the desktop.
Open TCC enter command like "echo StringWith$Sign", execute the command and the mark, copy and paste. At the position of the dollar sign you'll get a blank, and when you execute the command, the result will be "StringWithSign" (without the blank).
HOWEVER: I have also tried to create a virtual vanilla Windows from same image but using US instead of DK for all prompts. And I have to admit that the problem does not exist on this machine. How do I convince Microsoft, that there is a locale problem in Windows 1803, but only on third party software?