HTTPS Connections Timeout with Decryption Enabled

Problem: Client Application Cannot Reach HTTPS Site when Fiddler Classic is configured to decrypt HTTPS traffic.

This issue occurs on Windows Vista or later.

Solution 1: Customize Fiddler Classic Rules to force SSLv3 handshake

  1. Click Rules > Customize Rules.

  2. Add this code to the OnBeforeRequest method (where "" is the hostname of the destination server):

    if (oSession.HTTPMethodIs("CONNECT") && oSession.HostnameIs("")) 
      oSession["x-OverrideSslProtocols"] = "ssl3"; 
      FiddlerApplication.Log.LogString("Legacy compat applied for inbound request to"); 

Solution 2: Modify .NET application to force SSLv3 handshake

Use this code in your .NET application:

    ServicePointManager.SecurityProtocol = SecurityProtocolType.Ssl3;

See Also

"How do you get a System.Web.HttpWebRequest object to use SSL 2.0?" at

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