ostu - troubleshooting vpn with wireshark (by tony fortunato)

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© 2008 www.thetechfirm.com Wireshark QuickStart Tony Fortunato, Sr Network Specialist The Technology Firm Troubleshooting With A VPN Client

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Tony Fortunato is a Senior Network Specialist with experience in design, implementation, and troubleshooting of LAN/WAN/Wireless networks, desktops and servers since 1989. His background in financial networks includes design and implementation of trading floor networks. Tony has taught at local high schools, Colleges/Universities, Networld/Interop and many onsite private classroom settings to thousands of analysts.

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Page 1: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

Wireshark QuickStart

Tony Fortunato, Sr Network SpecialistThe Technology Firm

Troubleshooting With A VPN Client

Page 2: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

What are you talking about?

In some cases you need to troubleshoot through a VPN connection Some analyzers just show you encrypted ‘mumbo jumbo’ (yes it’s a real word,

look it up) You need to see the real data being transferred To complicate things, you may need to do this using a wireless connection,

which some commercial analyzers don’t natively support And of course some VPN vendors create ‘virtual adapters’ to confuse you further

In this example, I’ll use Cisco’s VPN and Microsoft’s client, since I run into them often

Page 3: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

What People Typically Do

The logical approach would be to capture packets from your network interface. Unfortunately many VPN clients use their own interface In the screenshot below, I pinged the default gateway with the Cisco VPN client

connected, but don’t see any evidence of it

Page 4: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

TIP: Launch Wireshark Quickly and Easily

The easiest way to determine which adapter to use is to select Capture->Interfaces after you VPN in and continuously ping something

Page 5: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

Results

Now when you capture from the correct interface you can see all you data in clear text (if the application is in clear text)

In this example my pings are clearly visible

Page 6: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

Microsoft interface

For the Microsoft client, I used the same methodology to determine the correct interface.

Page 7: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

Microsoft Client Bonus

If you select the Microsoft Client and connect, you can analyze the login process.

Page 8: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

Wrong Microsoft Login Credentials

Page 9: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

Wireshark Training - QuickStart

Tony Fortunato, Sr Network SpecialistThe Technology Firm

Thank you

Page 10: OSTU - Troubleshooting VPN with Wireshark (by Tony Fortunato)

© 2008 www.thetechfirm.com

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