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How can I monitor an EXE file when it is running to see what URL it is connecting to? I assume there must be free software out there that can do this fairly easily?

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Any firewall that monitors outgoing traffic should tell you. Set the firewall running, then start the program. It's request should be logged and then you can find the URL. – ChrisF Jan 26 '10 at 20:06
up vote 10 down vote accepted

For in depth analysis, Wireshark is your best bet as Phoshi has already mentioned. For a quick look at the URL, you can use netstat from the command line, or TCPView.

alt text

C:\Documents and Settings\Administrator>netstat -b

Active Connections

  Proto  Local Address          Foreign Address        State           PID
  TCP    john:1969    

  TCP    john:1604      ESTABLISHED  2904

  TCP    john:1716              79-114-229-43:60126  ESTABLISHED        732
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+1 didn't know about console netstat – whitequark Jan 26 '10 at 19:30

Try Wireshark - it's just about the best out there.

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+1 for Wireshark as well :) – Glen Y. Jan 26 '10 at 19:47

If you want just the "URL" part, SmartSniff is one of the easiest tools. It can be used as a generic packet sniffer too.

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Out of the box I believe you can also find this out with netstat command. But I don't know for sure anymore because I am not running windows(only when really necessary) anymore.

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Try Fiddler. It's a proxy for doze, which registers itself as the system proxy. If your application uses the system proxy (it might bypass it) then its requests will be intercepted by Fiddler when it's running.

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