http://www.w3.org/Provider/Style/URI.html describes that "cool" URIs don't change and don't expose details about the technology.
http://www.w3.org/TR/cooluris/ provides further details when it comes to semantic web (RDF) URLs.
The question I have is: can https URLs ever be considered cooluris in this regard?
It seems to me the best way is NOT to use https to identify things in RDF, but only http. Many servers nowadays automatically redirect http to https for publicly accessible resources (especially if you have an account at that site).
What do you think?
I don't see why you couldn't use https URIs. First of all 'S' in https means secure and not SSL. Hence it doesn't expose technological details. As long as you stick to https forever, this shouldn't make a difference
However a 303 redirect is commonplace in the Semantic Web. It may be better use http URIs as identifiers and redirect. You could even redirect to a different document based on intranet (http) or extranet (https) if that's desired and keep the id stable.
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