Have any of you actually done this? I'm looking to see what opinions are on it. There's apparently some sort of software you install on your server and it automagically takes care of it.
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Do you mean a "Self Signed" Certificate?
I've heard good things about Let's Encrypt https://letsencrypt.org/. They have their own roots but are cross-signed by trustworthy CA's. Not all hosts support them yet though.
Lets Encrypt is pretty awesome, but I don't know that I would use it for a "production" web site yet. The scripting portion of it is pretty nice that it auto renews, but like stated above they get flagged on some browsers.
What are you using it for? Work or home?
what domain do you run and what do you do with it?