We use a source control provider (Perforce) that makes files that are not checked out read-only. I checkin the .vgdbsettings files into source control, so normally they are read-only until I check them out.
I noticed that if I forget to checkout a .vgdbsettings file and try and use the GUI to make a change, press OK will close the dialog and silently ignore the changes that were made. It seems like it should either produce a warning that the file couldn’t be updated or use Visual Studio’s API to try and checkout the file.
I manually update my makefiles now, but before when I had VisualGDB update them for me, it seemed to have the same problem if the Makefile was read-only.