It was indeed finder zipping the files incorrectly. The root directory was being added to the front of the path for each file which caused the program to not be able to find the paths correctly. I was able to solve this issue by first unzipping the file using finder. Code signing the binaries and then going back into the folder with the unzipped folder "python37" running the command cd python37 zip -r python37.zip ./* And then moving the zipped folder out of python37 and into lib. Thanks eskimo for the help, very insightful response.