LetsEncrypt 

Even though it's a single point of failure the appearance of LetsEncrypt has been an important factor in the re-decentralization of the web.

I first started running gnusocial some time in 2015. I would have started earlier but I only had a single TLS certificate to be used sparingly and didn't particularly want to run it unencrypted, given firesheep and all that. Self-signed certs were also an annoyance since they tended to produce a lot of browser warnings.

The cost and complexity of obtaining CA certificates was a limiting factor before LetsEncrypt.
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LetsEncrypt 

@bob Still can be a nasty cost, though honestly there doesn't need to be. After all, what actual work are you paying for? I've always thought of it that way. It takes a few clicks at most to get a certificate, so, in all honesty, we've been screwed until they came along.

re: LetsEncrypt 

@cambridgeport90 Pre-letsencrypt getting a CA certificate could be quite costly, but even though free ones were available the procedure for obtaining and installing them was cumbersome even for someone with technical skills who knew what all the terminology meant. So there was some cost in terms of time.

re: LetsEncrypt 

@bob Definitely a very good popoint, there.

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