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We have an old application that worked for years, and recently a provider who supplies data for this application changed something on there end. Needless to say they say they say its not a problem on there end. Unfortunately we dont have the compiled code any more for this application. What I was wondering is, is it possible with IIS to monitor the outgoing SSL traffic. I dont have the private key, so I cant use wireshark because all I will see is the encrypted data. I need to know what URL is being requested so I can show the company that our program is still hitting this URL and that they need to turn that URL back on. I also thought about fiddler but we run IIS as a network service.

Any ideas on how I can get IIS 6 on a Windows 2003 server to record the outbound traffic URLs.

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what is the key length? – Hex Oct 26 '12 at 18:54
The length is 256. – josephs8 Oct 26 '12 at 19:12
Have you considered setting up a MITM SSL proxy? It should be pretty easy to hack something together pretty quickly with stunnel, if the client/server doesn't doesn't do very good checking. – Zoredache Oct 26 '12 at 19:54

Check out Fiddler. Plently of details on their site how this works:
It creates is own cert and adds it to the local machines trusted roots to do a MITM like Zoredache mentions. Here you can see that while I browsed "" the URL redirection was made to /us/index.htm and then /us/welcome.c

enter image description here

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oops... missed where you mentioned Fiddler in your post. Export Fiddler cert to a file. To modify Network Service certificate store: Launch MMC, Add Certificates, Select Service Account, Select Local Computer, Select World Wide Web publishing service. Add the Fiddler cert to trusted roots here. – Craig620 Oct 29 '12 at 20:52

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