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I can’t arbitrate here, but can add my anecdote to bolster what the person above is saying: I regularly remember clicking next on webrings and eventually getting a 404 with no way to progress. This was fairly regular to the extent that I sometimes just avoided clicking the webring modal.

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Yeah, I remember it both ways. Sometimes you'd click on a link at the bottom of one page to hit a dead end, but you could also go to the homepage of the webring itself and you could navigate through the sites in an iframe where you'd still run into a bunch of 404s, but you'd at least still have a "next" button in a separate frame so you could roll the dice again.

Webrings require maintenance to be useful and worth using, just like search engines do. The better maintained and curated they are, the more useful they will be.

> just like search engines do

Given how easy it is to run PostgreSQL and full text search these days, I think boutique search engines for small communities makes more sense than a webring.

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