We extensively use File / Directory Transfer and the files and Directories are different for the different calls.

1) The "Process" is overcomplicated, NOT intuitive, NOT user-friendly and NOT productive.
It is a life-important feature.
Somehow, in "GoToResolve" it changed from "inconvenient" to a "DISASTER".
- It is a productivity "Show Stopper".

2) The GoToResolve Directory Transfer "Process" is overcomplicated, NOT user-friendly and NOT productive.
To send a Directory you have to leave the remote Support Session enter password send a Directory(s) and then re-enter password to return to the Support Session plus waiting to continue session or extra clicks to bypass waiting.
- A clear productivity "Show Stopper";

3) Unfortunately the last used directories from the previous session with the Customer are not remembered.

Drilling down each time to the required location from "My Documents" both on the Customer and agent side takes lots of time. - COUNTERPRODUCTIVE!

4) Have you resolved an issue with the "Destination not writable" - when the file transfer will crash in the middle of transferring a few dozens of files?

5) For the inspiration could you kindly look at the Norton Commander, Volkov Commander, PC Anywhere, AnyDesk UI's...

It is a known issue since the GoToAssist times.

Asked the same question 5+ years ago on the GoToAssist Community.
The answer was that it is "not a priority".

Hope that the USABILITY and PRODUCTIVITY are now a PRIORITY.

P.S.
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Had to copy everything to notepad and then back into the form, "Preview", "Post" .

Poor file/directory transfer capability and UI even compared to GoToAssist