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I have been having a lot of issues for the last two weeks trying to sign and distribute a 3rd party MacOS app. I am unable to sign an app with Xcode properly because Xcode is saying that I do not have the Network Extension entitlement when I have it enabled both in Xcode and in the Apple Developer portal.

I am not a paid Apple Developer, but I am part of a team and I have the correct keys from the creator of the team (who is a paid developer). I am able to sign other apps and distribute them using the codesign tool but as soon as I try to sign the app with entitlements I run into issues.

Sending the app to other people results in it exiting with a Killed 9 or a SIGTERM which I assume is indicating that there is something going wrong in the signing.

This is the error I am getting when selecting the provisioning profile that I created in the developer portal

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In Xcode I have it enabled though

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And it is also enabled in the developer portal

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Even with that I am getting this issue when attempting to sign it with that provisioning profile

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So I am very confused. I am using the correct bundle ID, I have set everything up correctly as far as I can tell and I am still unable to sign and distribute this application. I am sure that there is something simple that I am missing here but I have no idea what that might be.

  • If the paid developer, the "team agent", (I'll assume that it is an "individual" developer account), builds the app, does it work? – benc Dec 2 '18 at 3:28
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The first thing I would do is check to confirm that you're using all the correct certificates. In particular, do the certificates at your end (within Xcode) match what's at Apple's end?

You can start by:

  1. Launching Keychain Access (by default it's in /Applications/Utilities)

  2. At the top of the left pane, select the login option under the Keychains heading

  3. At the bottom of the left pane, select the My Certificates option under the Category section

  4. Now check all the certificates to ensure they each have a disclosure triangle (it appears before the certificate name)

  5. Verify that all of the certificates are valid (i.e. when you click on the certificate name, you'll see a description at top of the window and it should have a green circle with a tick in it and a message stating “This certificate is valid.”

  6. Now also verify that the certificate(s) pertaining to the app in question matches up with the certificate at Apple's end.

Let me know how you go.

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Well, I never found out the issue, but I suspect it has to do with some improper error messages and poor documentation.

I didn't need NetworkExtension to begin with, but I thought it was required to use the Personal VPN extension. By disabling Network Extension and clicking "Fix Issue" under the Personal VPN extension I was able to export the app and get everything to work as intended.

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For anyone wanting to use Network Extensions in their macOS app:

Developer ID provisioning profiles actually don't support the Network Extensions entitlement. Development and App Store provisioning profiles on the other hand do support it. It's not well described in Xcode or the developer site (which show it as enabled). It's not until attempting to distribute an archive with the Developer ID provisioning profile that you will see that it is not included, or by running security cms -D -I Developer_ID.provisionprofile.

See question #8 in this Apple developer forums post: https://forums.developer.apple.com/thread/67613

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