I've read several guides/stackoverflows but not found a similar situation/solution.
I have my remote ssh working (can browse files).
I don't get why I need a local Windows application (although I have a compiled .exe it's not the version I want to debug which is only on the Linux server).
When I try and launch a remote debug session it immediately fails with
Exception occurred during launch
Reason:
Error during file upload.
and below in the details
Could not write file: <my windows exe path>
Permission denied
...
The aforementioned file is writable and in any event I also started eclipse as administrator just in case.
In any event the .exe is irrelevant. I just want to debug code remotely.
(I know all about gdbserver...happy to manually kick that off if need be....don't think I'm there yet though)
Below is the options page I'm presented with:

Had the same experience on TI Code Composer Studio Version: 9.3.0.00012.
This seems to happen while uploading the cross compiled binary from host to target. If you set the check box "Skip download to target path" the error should disappear. I propose to workaround the upload.
python.exe -m http.server --directory \source\hello\Debug\would be sufficient