Persistent S/MIME problems in Mail.app

I have had consistently spotty problems using Mail.app with Thawte personal freemail certificates to encrypt and sign mail.
I've had the certificates installed for a while, but have never been able to test them, but yesterday I got an encrypted message. I was able to read it, but whe I tried to reply, I was not able to encrypt the reply. Neither the encrypt nor sign buttons appeared. I verified the case of email address in the certificates, and verified I had private keys, for everyone, but no luck.
On the advise of another forum, I removed and refetched all the certificates, but that broke it completely and now I am unable to read encrypted messages. I ended up creating a new pair of certs and importing those. Now I can send encrypted mail, but still not read the old messages encrypted with the original certs, nor can I read new messages encrypted with my new certs. This problem is driving me insane, and I can't for the life of me figure out why I can't get this to work completely.
I have an idea that this should not be nearly this hard. Perhaps there is something obvious I am missing?

Yes! Are you pondering what i am pondering?
After numerous tries last year with leopard i finally got it to work:
Safari 4.0.2
Keychain 4.0.2
Open keychain and delete the old certificate.
Open Safari and go to Thawte website, choose quick login -> personal e-mail-certificates.
request a new certificate with the standard settings (choose x.509 and Mozilla Firefox/Thunderbird, Netscape Communicator/Messenger).
Wait until the certificate is issued.
Go to view certificate status and klick on Navigator. Fetch the certificate.
Restart Mail.app, create new message.
This worked for me. The Buttons for Signing E-Mails appear now in Mail.app

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