Gregory's Server#Smithereen update: the media cache now works for photos inside posts too. And, most important part of it, it now also deletes old files when the configured cache size is exceeded. Unlike some other implementations that store terabytes of cat pictures indefinitely 😏
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Images are only downloaded when they're first accessed and there's a cache miss. This works through a special endpoint I have that downloads the original image, generates a bunch of sizes and then redirects to the appropriate one. Any following page loads have direct links to local copies instead of that endpoint.