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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0 points

Not the only use cases, but you’d need a different service if you need/want wildcard certs, certs that are manually installed and managed, or certs with a longer expiration.

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12 points

Letsencrypt issues wildcard certificates. This is however more complicated to setup.

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11 points

I’d say they’re actually easier, at least in my experience. Since wildcard certs use DNS-01 verification with an API, you don’t need to deal with exposing port 80 directly to the internet.

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1 point

Yes, it can be easier. But not every DNS provider allows API access, so you might need to change the provider.

(good luck with that in many enterprise scenarios).

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2 points

Whoa, really??? I guess I just assumed nothing changed in the last 5 years. I need to look into that.

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2 points
*

I’ve set it up fully automated with traefik and dns challenges.

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1 point
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5 points

You can get wildcard certs with LetsEncrypt (since 2018): https://community.letsencrypt.org/t/acme-v2-production-environment-wildcards/55578

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