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?

Possibly linux
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Let’s Encrypt is a non profit largely started by the Electronic freedom foundation (eff) to bring https to the internet. Before it was very trivial to spy and modify web traffic but now that https is everywhere it is much harder to do if not impossible. They are also the ones who pushed for all major browsers to adopt https only. In all major browsers you should get a page warning you that a site uses http instead of https. It is a very bad idea to use http in 2024 as it allows anyone along the line to modify traffic and to see what pages you are viewing.

Terrasque
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I still use http a lot for internal stuff running in my own network. There’s no spying there… I hope … And ssl for local network only services is a total pita.

So I really hope browsers won’t adapt https only

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I do to. However, that’s the exception. I hope you aren’t running http over the public internet as that’s a massive security issue

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