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I have a similar issue with one of the sites that I would like to use through OmniWeb (SP7) and cannot as well. I get the repeated certificate question over and over, but it's on the same web page. It continues until I cancel.

The site in question is a SuSE Linux Openexchange Server 4. It should also be pointed out that IE (on windows) and Safari have problems with this site too, but not in the same way that OmniWeb does. Firefox seems to be the only browser (family) that properly deals with an OpenExchange Server site over https, at least how this one is configured.