Cisco Cisco Web Security Appliance S370 사용자 가이드

Also see: 

For transparently redirected HTTPS requests, the Web Proxy must contact the destination server to 
determine the server name and therefore the URL category in which it belongs. Due to this, when the 
Web Proxy evaluates Routing Policy Group membership, it cannot yet know the URL category of an 
HTTPS request because it has not yet contacted the destination server. If the Web Proxy does not know 
the URL category, it cannot match the transparent HTTPS request to a Routing Policy that uses a URL 
category as membership criteria.

As a result, transparently redirected HTTPS transactions only match Routing Policies that do not 
define Routing Policy Group membership criteria by URL category. If all user-defined Routing Policies 
define their membership by URL category, transparent HTTPS transactions match the Default Routing 
Policy Group.

If the HTTPS request comes from a client that does not have authentication information available from 
an earlier HTTP request, AsyncOS either fails the HTTPS request or decrypts the HTTPS request in 
order to authenticate the user, depending on how you configure the HTTPS Proxy. Use the HTTPS 
Transparent Request setting on the Security Services > HTTPS Proxy page to define this behavior. Refer 
to the Enabling HTTPS Proxy section in Decryption Policies chapter.

When scanning packet captures, you may notice that the “Client Hello” handshake is sent at different 
times for custom category and default (Web) category HTTPS Decryption pass-through policies.