Thank you. I see, so I was using the wrong type of certificate and that's why notarization was failing. Thank you for your help so far. With the correct cert, I have hit another blocker: I sent off the certificate signing request and downloaded the correct certificate and imported it into keychain access. It has the name: "Developer ID Application: COMPANY REDACTED (REDACTED ID)" Green check mark: "This certificate is valid". I see other information like the issuer: "Developer ID Certification Authority" "Apple Certification Authority" This matches what you mentioned above. Just making sure. And, I have removed the old certificate from keychain access and disk so it won't interfere. I mention this because of the below blocker. To my knowledge, this does not look like a self signed cert. Which... would be weird as I downloaded it from the certificate signing request. When I go to code sign now: codesign -s "REDACTED ID SAME AS DEVELOPER ID APPLICATION CERT" -f --timestamp -o runtime -i "com.redacted.hello_world" ./test_program.exe I get the cryptic error: Warning: unable to build chain to self-signed root for signer "Developer ID Application: REDACTED NAME (REDACTED ID)" ./test_program.exe: errSecInternalComponent Additionally, should I continue on this thread or create a new post. Thanks