Compiling pillow for a debug build fails without -j1 because distutils parallelizes the build, but there are problems with locking the .pdb file during when compiling the C files.  An example of the error message from a cl.exe command is:

fatal error C1041: cannot open program database 'C:\src\tmp\pillow-test\Pillow-7.2.0\vc140.pdb'; if multiple CL.EXE write to the same .PDB file, please use /FS

Building works with setup.py build_ext --disable-jpeg --disable-tiff --disable-zlib --debug build -j1

My guess is the fix is not to parallelize by default in a debug build; a /FS arg to cl.exe could be used, but that doesn't seem to be recommended.

I realize this might be considered a pillow bug, but my guess is that it affects other packages as well

If you're building through setuptools, then it's a setuptools bug (they own distutils going forward). https://github.com/pypa/setuptools

If you're not, please try with setuptools in the picture. It shouldn't require any more than just importing its "setup()" function instead of distutils's.

It is a setuptools bug and I've opened a setuptools issue at https://github.com/pypa/setuptools/issues/2442

Thanks!