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Certificate trust issues - is there any workaround?

I'm an IT Engineer in big company and i often see annoying troubles with Wi-Fi connection and secured (SSL) SMTP in Mac OS X.

Some MacBooks works fine, some with exactly the same software version cannot trust certificates of our authorization server for wi-fi and also cannot send mail via SMTP with SSL (i think this is trust issue too).

So now i have in front of me MacBook Air with Mac Os X 10.6.8. It had worked well but now it has same issue with mail and wi-fi at same time. So i think it have one reason. It also tell me that Mail server certificate is out of date after 11 May 2011, but actually there is a new cert on server issued 12 May 2011.