HTTPS Connections Timeout with Decryption Enabled
Updated on Nov 6, 2025
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
- Click Rules > Customize Rules.
- Add this code to the OnBeforeRequest method (where "HTTPSsite.com" is the hostname of the destination server):
c#
if (oSession.HTTPMethodIs("CONNECT") && oSession.HostnameIs("HTTPSSite.com"))
{
oSession["x-OverrideSslProtocols"] = "ssl3";
FiddlerApplication.Log.LogString("Legacy compat applied for inbound request to HTTPSSite.com");
}Solution 2: Modify .NET application to force SSLv3 handshake
Use this code in your .NET application:
c#
ServicePointManager.SecurityProtocol = SecurityProtocolType.Ssl3;See Also
"How do you get a System.Web.HttpWebRequest object to use SSL 2.0?" at stackoverflow.com