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www.ietf.org/rfc/rfc2616.txt

4.2 Message Headers

The order in which header fields with differing field names are received is not significant. However, it is "good practice" to send general-header fields first, followed by request-header or response-header fields, and ending with the entity-header fields.

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Yes, if you're implementing a client or server, you should not depend on the order of the headers. Completely separately, when I have a command line client for debugging, I want to see the request and response exactly as they were sent/received, respectively.

> Instances of the same path and name will overwrite each other, with the latest instance taking precedence. Instances of the same path but different names will add additional mappings.

> When sending cookies to a server, all cookies with a more specific path mapping should be sent before cookies with less specific path mappings. For example, a cookie "name1=foo" with a path mapping of "/" should be sent after a cookie "name1=foo2" with a path mapping of "/bar" if they are both to be sent.

http://curl.haxx.se/rfc/cookie_spec.html

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