If I generate a free SSL certificate for my website using OpenSSL, is that any more/less secure then purchasing an SSL certificate for several hundred dollars?
The difference is you will have to have everyone that uses your site put a reference to your certificate in their trusted sites area.
The certificates you buy are already installed as trusted through contracts with the browser companies.
For some reason, the last time we at "work" tried to install our own certificate, no matter what we tried, we can't get it to recognize our certificate as distributed by a company we chose to trust. So we have to answer a popup everytime we bring up webpages on this particular server.
I'm not 100% sure, though I think it wouldn't make a difference.
I'm not an SSL guru here, so be open to any other ideas and info.
If you have access to your server, setup a certificate through OpenSSL and test it with test clients. If all is well, then you will have saved some money. The worst that can happen is you just remove the certificate if it doesn't bahave how you want.
Another thing to consider is that the purchased certificates from people such as VeriSign will come with somthing like the $250,000 warranty, somthing generated for free will not be.
With branded solutions you also get a whole host of other benefits, simply having the verisign brand on your website is likely to make your consumer feel more trusting and i'm sure you'd see an increase in sales as a result.
Also other large brands have colaborated with browser developers to include things like the green address bar you'll see in IE7, again not really a big deal, but to your more niave consumers they'll come to expect this after seeing it on large commercial sites like amazon.
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