一、原因：缺少DER entitlement

解释一下DER：DER is short fro Distinguished Encoding Rules and is a standard by which ASN.1 structures are transferred. ASN.1 is a standard by which data can be encoded and decoded no matter which platform is being used. ASN.1 in this specific case applies to data encoding

简单的说就是一种加密方式。

二、错误提示：validation failed because of missing DER entitlements

[MICodeSigningVerifier _validateSignatureAndCopyInfoForURL:withOptions:error:]: 74: Failed to verify code signature of /var/installd/Library/Caches/com.apple.mobile.installd.staging/temp.xbDKXR/extracted/Payload/*********.app : 0xe8008029 (The code signature version is no longer supported.)

三、解决办法：

3.1、看自己的macOS的系统版本：如果是macOS Big Sur or macOS Monterey，那么直接加上flag：--generate-entitlement-der 即可，

        【怎么加--generate-entitlement-der】：<1> xcode中build setting 中OTHER_CODE_SIGN_FLAGS：--generate-entitlement-der 

<2> re-sign，这个对单个APP可以

# Re-sign your app

% codesign -s "Signing Identity Name from Keychain" -f --preserve-metadata --generate-entitlement-der MyApp.app
...
MyApp.app: replacing existing signature

# Check your signature again

% codesign -dvvvvv  ActionExtensionHostSSO.app
...
Page size=4096
    -7=4ade7be00e0a7b6db853edc4843e7ece1eea646f6f13d1809f78fc50d8db461f
    -6=0000000000000000000000000000000000000000000000000000000000000000
    -5=1dfa58bd8ac3c4fb42142c1c4d28c436128b3a7460186a44526194fb690112bc
    -4=0000000000000000000000000000000000000000000000000000000000000000
    -3=ef08dbe5a7c355336e1fb571604b683ce1c54536cb59a6155a1d18387fd23f6e
    -2=5b730fa46ffd405fd88da9606d82eda9af7f460f6049047afc176163326f5a7f
...

3.2 如果macOS Mojave and Catalina以下的，在xcode下也可以编译成功，然后打包payload成ipa也可以安装。但是在archive下直接生成ipa不行，

这个必须就要升级macOS的系统了。因为这个--generate-entitlement-der新flag。

ref：

https://developer.apple.com/forums/thread/682775?page=2