Sure, there is a way to achieve this.
First you have to create additional listener on new port. You can achieve with the QuickExec command "!listen", more information how to use it here
. Then you have to reroute request coming to that new port using FiddlerScript. Fill the placeholders in the following code snippet and add it to your OnBeforeRequest method. Please, keep in mind that it is written in C# but if you are using JScript.NET you should convert it manually.
) && oSession.oRequest.pipeClient.LocalPort == <httpsPort>)
Then navigating to "https://<hostname>:<httpsPort>" should show you the page from your HTTP server, but with HTTPS encryption.
As a side note I want to mention that in order this to work properly, all machines that want to access your server through HTTPS should trust Fiddler's root certificate as Certificate Authority. Otherwise the browsers will show warnings that the certificate is invalid.
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