From what I can tell the core of this fix was to remove the need to add in the flag for --generate-entitlement-der to the Other Code Signing Flags. You mean in our case? if so... no that was not the problem. We already tried all possible solutions. The issue seems to have been fixed with the Xcode release. At least we hadn't updated or changed anything regarding our build prior to the xcode release but afterwards, it started signing properly.

The DER hash slots are not being added, even though I have done the same. I could try to update to Mac OS 11.6 and see if that fixes it but otherwise I am out of ideas. You can check out the sample project I added to the bug report and see if there's something funny going on.

FB9661051 (Watch and watch extension are not being signed with DER entitlements) Thanks in advance ;)

@sponlingam if the app is crashing upon launch then you probably still have a codesign issue. You can inspect the specific error by connecting your phone to your mac through usb, so you can see the console output from your watch via the Console.app Look for an error like this: UserInfo={SourceFileLine=646, NSLocalizedDescription=Got error 17 in install done from remote side (MI error ApplicationVerificationFailed ; Extended 0xe8008029 ; Desc Failed to verify code signature of /var/installd/Library/Caches/com.apple.mobile.installd.staging/temp.y3l1mI/extracted/Payload/Watch.app : 0xe8008029 (The code signature version is no longer supported.)), FunctionName=-[ACXServerInstallOperation receivedDictionaryOrData:]} If you get something similar, then your watch app or extension hasn't been signed properly. Make sure to sign in the order that meaton described. For you working fine? after re-sign app? Yes if I resign the app manually, then it works.