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Unable to view .ashx images

When trying to view .ashx images, we get a blank image with a red x.  Mainly on the alaska Airlines website (alaskaair.com) This is network wide (Server as well) on both wired and wireless connections. I have isolated a single pc straight into the firewall by itself and the images are displayed correctly.  Once the server is plugged back into the network the images are no longer displayed. I cant seem to locate where the issue is coming from, whether it be from a firewall policy or an IE policy.
I did not initially configure this server, so I'm not sure where to start.
I have tried with IE8-11, Firefox, Chrome, and Safari on the workstations.  They all yield the same results.

Firewall - Watchguard XTM22.
Switch - Dell PowerConnect 2824 Gigabit
Server - Dell T410
Workstations - Dell OptiPlex 7010 / Dell Latitude E5430

Running SBS 2008 sp2 with all Windows 7 Pro x64 workstations.

I have attached images that may be useful, one of how the webpage looks while the server is plugged in, another with the server off the network.

Please let me know if you need more information.
Thanks so much for your time.
C--Users-nathan-Desktop-With-Server-conn
C--Users-nathan-Desktop-Without-Server-C
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