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On Yosemite, that Workgroup Manager app doesn't work, neither did modifying the plist. This worked for me, in a terminal: defaults write com.google.Chrome AutoSelectCertificateForUrls -array defaults write com.google.Chrome AutoSelectCertificateForUrls -array-add -string '{"pattern":"https://[*.]my.domain:8090","filter":{"ISSUER":{"CN":"example.com"}}}'



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