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?

r00ty
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There’s a certbot addon which uses nginx directly to renew the certificate (so you don’t need to stop the web server to renew). If you install the addon you just use the same certbot commands but with --nginx instead and it will perform the actions without interfering with web server operation.

You just then make sure the cron job to renew also includes --nginx and you’re done.

@0x0@programming.dev
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Oh, that… I think i’m using it but it seems.to expect a response from 80 when all I have there is a redirect to 443.

I thought you meant an nginx plugin.

Shimitar
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Yes you need both 80 and 443 for certbot to work. Anyway having 80 to redirect to 443 is common and not a security risk.

r00ty
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I have auto redirect to 443. But --nginx works fine. I think it overrides stuff for whatever the specific url used is.

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