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Imagine you have a shared office DNS resolver (which is pretty common). That resolver would aggregate all of the requests into one shared, cached stream. Then the question becomes "hey Apple, one person of how ever many thousand are behind me would like to know if Adobe's certificate is still valid". That's reasonably anonymized, I think.

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Then the question is, "how much do I trust my ISP/DNS provider?"

Those DNS lookups tell your ISP 1) that you use a mac and 2) that you have an application from a specific developer installed.

I think I trust my ISP less than I trust Apple, here. Am I wrong to do so?

Well, back to the state right now where your ISP can see your plaintext HTTP packets if they want to, so it wouldn't be any worse than the current situation. I guess you could get much the same effect by configuring your company Macs to point at a shared Squid server to cache the GET requests from the OCSP server, but in practice almost no one does that.

Apple says they're going to move to an HTTPS based system, so the relevant comparison is between HTTPS and DNS, not HTTP and DNS.

That only helps if you have a shared resolver.

Pretty much everyone has a shared resolver at some point. Almost no one’s running a local resolver on their laptop these days.

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