I've been working with the Transparent Proxy portion of the Network Extensions / System Extensions in Catalina. When I try to proxy port 80, and go to a http site, Safari gives me an error "The operation could not be completed. Operation not permitted (NSPOSIXErrorDomain:1)". Other browsers (Firefox, Brave) seem to work fine. Data flows to and from both browsers and I see the metadata about those connections. Safari on the other hand, stops the communications altogether. When I turn the Proxy off, Safari works as usual. As you might imagine, https works fine, but I am not running a transparent proxy for port 443, just 80.
Thanks
Chris Parker