Why is the GnuPG-sign checkbox disabled in SourceTree?

You likely aren’t pointing the GPG Program setting (found in SourceTree -> Preferences -> Advanced) at the right bin. If you’re using GPGTools on OS X, it should be /usr/local/MacGPG2/bin. To navigate to the /usr/bin directory in the Open File dialog, click shift + command + g

SourceTree setting

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