I finally got past the huge roadblock of Mac app signing and notarization for Nucleate after more than a month stuck on it. I bought an Apple developer account and set up the signing certificates, but it wasn’t straightforward. At first, not all files in the app could be signed, which caused repeated failures that I misread as dependency problems. Also, I ran into a weird issue where SSH remote login couldn’t access the Keychain, so the signing process never completed remotely until I fixed that. That was a subtle one.

The notarization itself took way longer than expected—over 24 hours instead of the usual 15 to 60 minutes. I’m not sure why it dragged on so long, but the good news is the app now runs on Mac without triggering Gatekeeper warnings. Next up, I need to staple the notarization ticket to the .dmg file and validate the signature before I can call it done on the Mac side.

I’m keeping the app bundled on Mac for now instead of renaming it. I’m still not sure if renaming would break anything or just make the release more complicated, so I want to avoid that uncertainty for the moment.

On the Windows side, the .exe version works but still needs signing. That process seems simpler than Mac signing, but I haven’t nailed down the exact workflow yet. I’m prepping a Windows beta release but haven’t finalized the signing steps, so that’s next on my list after wrapping up Mac notarization.

I also realized GPT gave me some incorrect advice on signing issues, which didn’t help the confusion. I’m planning to send the signed Mac app to my brother for feedback to see how it performs in the wild before moving forward.

Still have some open questions about whether renaming the Mac app will cause problems and what the best Windows signing workflow is to avoid delays. But at least the Mac signing nightmare is mostly behind me now.

Two-Line Takeaway

Key step forward

The most important forward progress step was successfully overcoming the Mac app signing and notarization process, allowing the app to run without Gatekeeper warnings.

Significant barrier or risk

The most important barrier was the complex and time-consuming Mac signing process, including issues with file signing, SSH keychain access, and unexpectedly long notarization times.

Keynotes

Decisions & Observations

• Decided to purchase an Apple developer account and set up signing certificates to resolve Mac app signing and notarization roadblocks.

Issues & Next Steps

• Needs to staple the notarization ticket to the .dmg file and validate the signature to complete the Mac release process.
• Will keep the Mac app bundled without renaming to avoid potential release complications until more is known.
• Needs to finalize the Windows .exe signing workflow before preparing the Windows beta release.
• Will send the signed Mac app to a tester for real-world feedback before proceeding further.
• Needs to resolve uncertainty about the impact of renaming the Mac app and determine the best Windows signing workflow to prevent delays.

Generated with Nucleate by Watchlight Studio — distilled from full transcription.