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 point of paid SSL at this stage in the game are the higher tiers of verification. Instead of just verifying that you own the domain, you can verify that you are who you say you are. These are called Extended Validation and Organizational Validation certificates. This has historically been desirable by businesses. It used to be that these higher tier certs would not only give you a lock icon in the address bar of a web browser, but also a little blurb confirming your organization is legit. Not sure if this is still the case though. You will see the extended validation when you check the sites certificate though for sure.

As far as encryption and security, there’s no difference. Also side note, the Comodo brand still technically exists but it was bought by Sectigo like 7 years ago.

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