If we are writing a custom http client which connects with an https server. Should the custom client when deployed on machines which are behind web proxy need to send a HTTP CONNECT Request so as to establish a connection with the https site, OR

Can it just do a Direct Request (say GET) to the https site?
If the above is possible what are there any issues/concerns? For Ex: Proxy's dont allow direct SSL connection as it does not know to which external address it is connecting? Is this one of reasons.

With https inspection available with Web Proxys

Like for TMG there is HTTPS Inspection Settings. http://blog.blackfoundry.com/2011/06/02/break-open-dropbox-ssl-traffic-with-squid-proxy/ The above link says of ways to inspect https traffic. Do proxies still bar outgoing direct ssl connection?

Thanks a lot...

closed as off topic by Rory Alsop Jul 4 '12 at 17:00

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You are trying to compare apples with pears. There is a difference between an HTTP proxy and site that serves http over ssl.

The former is a server that is used as an intermediary to do requests, depending on the type it will either conceal the clients or servers identity.

The latter is a protocol that is used to serve pages over a secured connection, so no eavesdroppers can see what's being requested. The server knows the identity of the client.

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