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I have a series of codesign commands that I would run regularly to sign my app. They always worked fine, until I recently upgraded my Mac OS to Monterey and XCode to 13.3.1. Now the same syntax just results in codesign's usage message. Here's one of the commands that fails: codesign --deep --force --verify --verbose --timestamp --options runtime --entitlements "example.entitlements" --sign "Developer ID Application: Company Name (XXXXXXXXXX)" I tried variations also, to no avail, such as this: codesign -s "Developer ID Application: Company Name (XXXXXXXXXX)" --options runtime --timestamp --force --deep --entitlements "example.entitlements" Any idea what I'm doing wrong, and why it stopped working after upgrading? Thanks.