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I got to say you're spot on. Keeping things working is no challenge looks at his commodores . Keeping them relevant is more of a challenge, this is one reason I hate to see people forcing redirects to HTTPS, it's just great and dandy that modern browsers suggest this to users (as long as they don't force), but for vast vast amounts of information, in the free world, you shouldn't force people into always-encrypted. T…
There is one reason I can think of for encrypting websites, it tells you the information is coming from where you expect and not an interloper. I agree its worth thinking about about serviceability and longevity but I can't help feeling like it would be like worrying about keeping a PDP 11 running for fifty years.
Just think about all that unauthenticated information in libraries. Anyone can replace pages in the books. Books can be substituted with completely fake copies. No one bothers to do this for the same reasons no one bothers to MITM connections to plain text web sites.