A customer wrote that he urgently needs support for S/MIME. As I always wanted to add support for encrypted emails it sounded like a good idea to get started with S/MIME.

As as developer I don't know everything. I mostly do databases and email. VBA I can do in my sleep as well as designing data. So S/MIME is a totally new topic for me.

To get started I Goggled a bit and found a guide by Apple. According to them using S/MIME was:

1. Get certificate.
2. Install certificate.
3. Relaunch Mail.
4. Use S/MIME.

1. Get certificate
That sounded simple. So where do get a certificate? Goggling again I found a free solution. I applied for a certificate. Got the reply mail with a large, red non-working button and a link. In there it was mentioned that I have to use Firefox. No reason given. I thought: why? Downloaded the certificate.

2. Install certificate
I double clicked the certificate and got a cryptic error message with just a number and no explanation. Back to Goggling again I found that others had the same error, too. But nobody explained what the error message meant.

I wasted so many hours because Apple wasn't able to write a decent error message.

In the evening a friend helped me out. After quite a while we found out that the certificate didn't contain a crucial piece of information: the private key. Without it the certificate is worthless. This key lands somewhere in Firefox when you download the certificate. Which I totally missed.

I now rechecked the instructions that come on the website. There is nothing at all about the certificate landing in Firefox. Remember, I'm a newbie in some things, too.

Oh, and I still get an error when importing the complete certificate into Keychain.

Sometimes I just love computers. I'm now going to create my own certificate. Thank you very much, Comodo and Apple, for giving me so much fun.