When llvm-rc loads an external file, it looks for it relative to a number of include directories and the current working directory. If the path is considered absolute, llvm-rc tries to open the filename as such, and doesn't try to open it relative to other paths.
On Windows, a path name like "\dir\file" isn't considered absolute as it lacks the drive name, but by appending it on top of the search dirs, it's not found.
LLVM's sys::path::append just appends such a path (same with a properly absolute posix path) after the paths it's supposed to be relative to.
This fix doesn't handle the case if the resource script and the external file are on a different drive than the current working directory; to fix that, we'd have to make LLVM's sys::path::append handle appending fully absolute and partially absolute paths (ones lacking a drive prefix but containing a root directory), or switch to C++17's std::filesystem.
There's an existing testcase for fully absolute paths, using lit's %t to expand to an absolute path. Making a testcase for this would probably require a bit more scripting in the test file, to strip out the drive name prefix from the absolute path, and embed that into a resource script.