WP Maintenance Manager ships from a single Python codebase to both Windows and macOS. "Python is cross-platform — write once, run anywhere," the saying goes. The reality is that the distribution pipeline is completely separate per OS, each with its own pitfalls.
PyInstaller / Inno Setup / Apple Notarization / eSigner — the release cycle is a combination of OS-specific toolchains. Here's the full picture, plus what to watch out for at each step. (The choice of internal architecture, Flask + browser UI, is covered separately in why we built a desktop app on local Flask + browser UI; this post is about distributing that architecture across two operating systems.)
The per-OS pipeline at a glance
Step
Mac
