Chrome AutoSelectCertificateForUrls OSX
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"}}}'