I imagine that the difficulty for some old sites is not the difficulties of obtaining a certificate, it's moving out of autopilot mode. Any change at all is harder than just paying your hosting company every year to keep on keeping on.
There's obviously a change here, and it might be difficult to do. One of the most important things, tho, is that once this is ecosystem-wide, TLS will become the default and every competent hosting provider will auto-upgrade these sites.
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So I hear what you're saying, but we need to understand that what we were doing before _was wrong_. It simply was.
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Fixing it requires change, in the same way that we're going to need to get fossil-fuel cars off the road to reduce carbon emissions.
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indeed - letsencrypt is easier then previous models - https://indieweb.org/HTTPS has some history. On the whole this is a good ratchet, but I understand the difficulty
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