E-mail certificate issue

Question

I guess I'm just a compete idiot and can't overcome simple problems, shame shame shame. However, I am trying to put a simple scenario together:

box A (Windows 7) and box B (Windows 8 inside a virtual machine). I want each of the two get e-mail certificates and be able to exchange emails securely. I registered with CACert.org and issued two certificates (sasha@host and agent@host). I was somehow able to install the first certificate into my personal storage and in result it does show in outlook and I am able to sign e-mails with that certificate and it will show under personal tabs in IE > content > certificates.

On the second box when I go to cacert.org to collect my certificate to the other email it will say it's installed but it will not show under personal tab (although I select the personal storage) but it will instead show under "other people" tab and hence outlook doesn't see it as a valid certificate for signing emails and so on.

This is driving me nuts and I can't figure how to do this. This certificates woodoo is so weird no wonder people don't use it very much.

Anyone able to help?

I guess I could be getting something totally wrong - but what?

Answer 1

I think the best thing you can do in the current situation is to install the certificate for Box B on computer A, where the key hopefully is. If so, you'll see it go into Personal certs.

Then you can export both the key and cert in a PFX file from there, make sure you include the key. Mark the key as exportable.

Once you get that, you should be able to import it into Box B. I would then do an export test on Box B and make sure you can export the cert and key from there (in case you need to rebuild B you should keep a secure copy of the key somewhere). If that works, you can delete the box B cert off box A.