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Troy-this issue unexplainably fixed itself yesterday. The certificate page also has a username/pw section which can be used as a substitute for the certificate login. Since reporting the problem, I have been revisiting the page regularly over the last 3 days. Each time I visit, I've tried the certificate login to see if anything is different, but no change. OW has been quit multiple times, all cookies have been cleared, etc... I have not logged out of the computer, although it has been slept (keychain set to lock after inactivity or on sleep) and taken between multiple locations. Yesterday evening, I went to the login page and once again hit the digital certificate login link. This time, OW put up the dialogs for granting access, instead of the keychain dialog, I granted permission always, and it is now able to use the new certificate. I expect to see the error page return at some point, as there is still an issue of the state of the keychain when I hit the login page. I really want to know what's going on with this, since this exact same issue happened last year (there is another post from me on it in this forum). Safari 4 picked up the change and asked for permissions on the very first attempt.