Introducting my own working theory here, ignore if you wish.

I'd think that the *first* thing that would have to happen is that the page
and the images it contains would have to be delivered in one stream.  There
are both HTML5 (resource bundling) and protocol (SPDY) mechanisms for doing
this.  Some URL rearrangement to consolidate hosts might be required as
well. But in the interest of being forward-looking I'd suggest taking some
implementation of resource bundling as a given.  Similarly, I wouldn't
waste time profiling both compressed and uncompressed data; assume the
bundle is compressed.

That leaves a simpler question: if the contents of a page (including
images) are delivered as a compressed bundle over a single host connection,
how easy is it to tell the what page I'm looking at from the size of the
response?  How much padding would need to be added to bundles to foil the
analysis?

Some extensions:
1) Assume that it's not just a single page at a time, but a sequence of N
linked pages.  How does the required padding depend on N?
2) Can correlations be made? For example, once I've visited page A which
contained image X, visiting page B which also has image X will not require
X to be re-downloaded.  So can I distinguish certain pairs of "long
request/short request"?
3) What if the attacker is not interested in specific pages, but instead in
enumerating users looking at a *specific* page (or set of pages).  That is,
instead of looking at averages across all pages, look at the "unusual"
outliers.
4) Active targetted attack: assume that the attacker can modify pages or
images referenced by pages.  This makes it easier to tell when specific
pages are accessed.   How can this be prevented/discouraged?
5) As you mentioned, disclosing user identity from read-only traffic
patterns is also a concern.

I'm afraid the answers will be that traffic analysis is still very easy.
 But it still be useful to know *how* easy.
 --scott
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