As far as I understand the specs, the ETag, which was introduced in RFC 2616 (HTTP/1.1) is a successor (of sorts) for the Last-Modified-Header, which is proposet to give the software-architect more controll over the cache-revalidating process.
If both Cache-Validation-Headers (If-None-Match and If-Modified-Since) are present, according to RFC 2616, the client (i.e. the browser) should use the ETag when checking, if a resource has changed. According to section 14.26 of RFC 2616, the server MUST NOT respond with a 304 Not Modified, if the ETag presented in a If-None-Match-Header has changed, and the server has to ignore an additional If-Modified-Since-Header, if present. If the presented ETag matches, he MUST NOT perform the request, unless the Date in the Last-Modified-Header says so. (If the presented ETag matches, the server should respond with a 304 Not Modified in case of a GET- or HEAD-request...)
This section leaves room for some speculations:
... o.k. While I was writing this, the question was boiling down to this answer:
The (small) contradiction stated above, was made because of Weak ETags. A resource marked with a Weak ETag may have changed, although the ETag has not. So, in case of a Weak ETag it would be wrong, to answer with 304 Not Modified, when the ETag has not changed, but the date presented in the If-Modified-Since does not match, right?
The difference between a regular (strong) ETag and a weak ETag is that a matching strong ETag guarantees the file is byte-for-byte identical, whereas a matching weak ETag indicates that the content is semantically the same. So if the content of the file changes, the weak ETag should change as well.
In the scenario you present, the file on the server may be newer than the cached copy in the client -- but since the ETag matches, it is semantically equivalent to the cached copy so it would be acceptable to return a 304 response.
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