Let's Encrypt was _huge_ in making it's absurd to not have TLS and now we (I, at least) take it for granted because it's just the baseline for any website I build. Incredible, free service that helped make the web a more secure place. What a wonderful service - thank you to the entire team.

The CEO at my last company (2022) refused to use Let's Encrypt because "it looked cheap to customers". That is absurd to me because 1), it's (and was at the time) the largest certificate authority in the world, and 2) I've never seen someone care about who issued your cert on a sales call. It coming from GoDaddy is not a selling point...

So my question: has anyone actually commented to you in a negative way about using Let's Encrypt? I couldn't imagine, but curious on others' experiences.

I only hear justified praises of letsencrypt. Also thanks to the EFF and developers of certbot, which massively improved the toolchain around certificate deployment. Not the favorite activity for admins, but this made processes like certificate renewal/revokation much more convenient.

I think the portion of users that check a certificate after the browser treated it as secure is well smaller than 1%, probably well below 0.1%. And I guess these TLS connoisseurs have a positive inclination to letsencrypt as well.

To be fair, for a CEO in 2022, EV certificates had only lost their special visualizations since September/October 2019 with Chrome 77 and Firefox 70 - and with all that would happen in the following months, one could be forgiven for not adapting to new browser best practices!

https://www.troyhunt.com/extended-validation-certificates-ar...

> The CEO at my last company (2022) refused to use Let's Encrypt because "it looked cheap to customers".

Spoken like a true dinosaur. How can a certificate based on open, public and proven secure protocols be cheap?

> So my question: has anyone actually commented to you in a negative way about using Let's Encrypt?

No, but I personally judge businesses which claim to be tech savvy if they don’t have an ACME issued certificate, because to me that instantly shows I’m not dealing with someone who has kept up with technology for the last 10 years.

I once notified Porsche that one of their websites had an expired certificate, they fixed it within a couple of hours by using Let's Encrypt. It surprised me.

Let's Encrypt is to the internet what SSDs are to the PC. A level up.

I have also heard a negative about it being somehow "cheap" and we can "afford" a proper wildcard for our website from managers back in the day, like, few years ago. Never mind the hours wasted every year changing that certificate in every system out there and always forgetting a few.

Also a valid point from security people is that you leak your internal hostnames to certificate transparency lists once you get a cert for your "internal-service.example.com" and every bot in existence will know about it and try to poke it.

I solved these problems by just not working with people like that anymore and also getting a wildcard Let's Encrypt it certificate for every little service hosted - *.example.com and not thinking about something being on the list anymore.

There was a time when EV certificates were considered more trustworthy than DV certs. Browsers used to show an indication for EV certs.

Those days are long gone, and I'm not completely sure how I feel about it. I hated the EV renewal/rotation process, so definitely a win on the day-to-day scale, but I still feel like something was lost in the transition.

Modern browsers are going out of their way to hide every bit of information about the website (including even the URL) — so I don't know how these customers would actually even find out what CA issued the certificate.

In Safari, I don't even know how to find that information anymore. When I want to check expiration dates for my own sites, I start Firefox.

There are extended certificates that did matter in our sales process for some hosted solutions back about 15 years ago if I recall right… no one has ever cared since…

No! Let's encrypt is easily the best thing that's happened for a secure internet the last 10 years.

The only pain point I had using letsencrypt, and it wasn 100% not their fault, was I tried using it to generate the certificate to use with FTPS authentication with a vendor. Since LE expires every 90 days and the vendor emails you every week when you’re 2 months from expiring, that became a pain point and it wasn’t easier to just by a 1 or 2 year cert from godaddy. Thank goodness that vendor moved to sftp with key authentication so none of that is needed anymore

Many host providers (Those acquired by companies like Web.Com, allegedly) disable all ability to use outside certs since Google made encryption a requirement in Chrome Browser...

They do things like blocking containers & SSH to make installing free certs impossible.

They also have elevated the price of their own certs (that they can conveniently provide) to ridiculous prices in contrast to free certs their customers can't even use...

It would be a huge price-fixing scandal if Congress had any idea of how technology works.

I've seen people complain that Let's Encrypt is so easy that it's enabling the forced phaseout of long-lived certificates and unencrypted HTTP.

I sort of understand this, although it does feel like going "bcrypt is so easy to use it's enabling standards agencies to force me to use something newer than MD5". Like, yeah, once the secure way is sufficiently easy to use, we can then push everyone off the insecure way; that's how it's supposed to work.

I have heard, but do not aggree, that Let‘s Encrypt is risky, because phishing sites use it. It’s implied that other CAs do checks against it.

Old browsers on old hardware without its CA baked in.

Seconding the effect of Let's Encrypt on the world of TLS. I remember getting into web applications in the late 2000s and rolling my own certificates/CA and it was a huge, brittle pain. Now it's just another deployment checkbox thanks to LE.

I have worked at companies that refused to use LetsEncrypt for the same reason.

> It coming from GoDaddy is not a selling point...

I just people who use GoDaddy. They were the one company supporting SOPA when the entire rest of the internet was opposed to SOPA. It's very obvious GoDaddy is run by "business-bros" and not hackers or tech bros.

> has anyone actually commented to you in a negative way about using Let's Encrypt?

A friend of mine has had a negative experience insofar as they are working for a small company, using maybe only 15–20 certs and one day they started getting hounded by Let's Encrypt multiple times on the email address they used for ACME registration.

Let's Encrcypt were chasing donations and were promptly told where to stick it with their unsolicited communications. Let's Encrypt also did zero research about who they were targetting, i.e. trying to get a small company to shell out $50k as a "donation".

My friend was of the opinion is that if you're going to charge, then charge, but don't offer it for free and then go looking for payment via the backdoor.

In a business environment getting a donation approved is almost always an entirely different process, involving completely different people in the company, than getting a product or service purchase approved. Even more so if, like Let's Encrypt, you are turning up on the doorstep asking for $50k a pop.