I’m curious what the benefits are of paying for SSL certificates vs using a free provider such as letsencrypt.

What exactly are you trusting a cert provider with and what are the security implications? What attack vectors do you open yourself up to when trusting a certificate authority with your websites’ certificates?

In what way could it benefit security and/or privacy to utilize a paid service?

And finally, which paid SSL providers are considered trustworthy?

I know Digicert is a big player, but their prices are insane. Comodo seems like a good affordable option, but is it a trustworthy company?

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The person isn’t talking about automating being difficult for a hosted website. They’re talking about a third party system that doesn’t give you an easy way to automate, just a web gui for uploading a cert. For example, our WAP interface or our on-premise ERP don’t offer a way to automate. Sure, we could probably create code to automate it and run the risk it breaks after a vendor update. It’s easier to pay for a 12 month cert and do it manually.

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