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Adding more to my previous reply. The system is unable to launch the helper app after re-login on macOS 10.15 and 10.14, but this mechanism works fine on macOS 11.0.
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I’m confused by what you mean by “prod singed apps”. Both the main app and helper app are signed by 3rd Party Mac Developer Application. You tagged your post with Mac App Store, which suggestions you’re distributing that way. Yes the app is meant for Mac App Store submission and I need to qualify the login item mechanism Are you seeing this problem with the app after you install it via the App Store? No. The LoginItem mechanism is not yet available in the App Store build. This is being added now.
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Hello I am facing the same issue with one of my app. The app uses SMLoginItemSetEnabled to register a helper application. I see this behavior on 10.15.7 and 10.14.6, but not on macOS 11.0 or 11.1. On the newer OS it works fine.