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What proportion of web requests are served from a shared network cache? Whenever network cache is brought up in relation to SSL, I always wonder. Surely it's only a few percent max?

I think the security gained from adding SSL far outweighs the efficiencies lost by losing a shared network cache.

Caching can be very useful - I've deployed proxy web caches in school situations, and it does wonders for speed when loading the same site on a lab full of computers all at once (and also preventing age-inappropriate content at school).

That's not a security sensitive situation - in cases where security is at issue, the best practice is to make secure pages as lightweight as possible so they'll transfer quickly on slow lines.

It's an issue for wireless (EDGE, 3G) and satellite networks. I think a lot of networks do some kinds of filtering and downscaling of images or videos.

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