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On Sonoma I develop with gcloud and python2.7 and python3.9 from MacPorts. I always get MULTIPLE dialogue pop-ups when starting the python webserver in Terminal.app Choices are not remembered (neither block nor allow!!) I tried to solve that with socketfilterfw and codesign but it has NO effect at all. Questions like this creep around since 10 years on Stackexchange. I am searching since several hours for a solution of this problem. Is there any solution? 20 : /opt/local/Library/Frameworks/Python.framework/Versions/3.9/Resources/Python.app ( Allow incoming connections ) 21 : /opt/local/Library/Frameworks/Python.framework/Versions/2.7/Resources/Python.app ( Allow incoming connections ) sudo codesign -s - -f /opt/local/Library/Frameworks/Python.framework/Versions/3.9/Resources/Python.app