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ssl onloading to more/different endpoints
I'd start with a capture on the server side to see what's going on. Assuming you're applying a server SSL profile and going to the site on its required port (443), then in the capture you should see the TCP 3-way handshake, and SSL handshake, and eventually encrypted data. Depending on the server it may require different cipher settings or an SNI (server name indication) in the handshake. If you can determine that it's failing after the TCP handshake, fire up an SSLDUMP and look inside the handshake:
ssldump -AdNn -i [external VLAN name or interface] port 443 [and any additional filters]
You'll be able to see inside the SSL handshake and when and where it's failing.
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