Well I've had some luck with MacOSForge Smart Card Services, I installed their 10.6 version and was able to get Keychain to see my SmartCard and keys, that let me use Safari to login into certain DOD sites, but not all. A lot of the DOD sites are written specifically for IE so the websites don't always work well with Safari, even with the User Agent set to mimic IE. link to the Smart Card Services wiki: http://smartcardservices.macosforge.org/trac/wiki I also looked at CACkey as that is needed for Firefox since it doesn't use Keychain access. I ran into problems with CACkey not seeing the smartcard reader correctly. This might be due to Smart Card Services, or it might be a 10.6 issue. I will try to uninstall Smart Card Services and reload CACkey only.