> Question 1: Are there any utilities that allow me to 
> monitor the outgoing traffic on my machine? Something 
> along the lines of "The machine sent X request to X 
> IP / port."  I figure I can run the program and see 
> where it is going.

Yes, there are many, many programs that can do this. If you have Windows NT
or 2000, you can install the Network Monitor program that comes with the OS.
Or, you can use one of these:

Ethereal: http://www.ethereal.com/ (free, open-source, requires the winpcap
driver)
CommView: http://www.tamos.com/products/commview/

You might just want to poke around on the winpcap site and see what's there.
The winpcap driver allows you to run lots of tools traditionally found only
on Unix, like tcpdump:
http://winpcap.polito.it/

With these sorts of programs, you'll see all activity on your network card,
and if your network card is running in promiscuous mode, you'll see all
activity on your network segment. This can be a little overwhelming. If you
just want to find out what ports are being used on your machine, you can go
to a command prompt and type "netstat -a". You can even pipe output to a
text file, and have that happen every second: "netstat -a 1 > myip.txt".
This won't actually tell you what's being sent or received, and unless
you're using XP it doesn't tell you which programs are using which ports,
but it lets you know what ports are being used, and you could then just
interrogate those ports yourself - if you're connecting to some server's
port 21, it's probably an FTP server.

> Question 2: Is there a way to automate a GUI program?  ( 
> Doesn't that defeat the purpose of a GUI program in the 
> first place? ).

This depends on the specific GUI program, generally, in that some GUI
programs may expose COM automation interfaces. Also, there's an interesting
new product out there which allows you to automate GUI programs. It's called
Digital Cortex, from Anysoft. I know some of the people over there, as they
used to work for Allaire. This may be overkill for what you want, but who
knows?
http://www.anysoft.com/products/developer/index.asp

Dave Watts, CTO, Fig Leaf Software
http://www.figleaf.com/
voice: (202) 797-5496
fax: (202) 797-5444

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