I was finally able to figure out the solution to this little problem. Seems that when I updated the firmware of the Linksys router it reset the option for MTU. It cranked the value to high and turned it off. I was able to ping my ISP and figure out the correct MTU setting, once I turned it back on and tested my Outlook on both computers everything worked fine.
Thanks to all for your suggestions, hopefully this helps someone else in the future.
For those who are unaware (like I was) of this MTU thing. You can use this FAQ from Linksys to figure the proper value setting. It applies to Linksys but should be useful for other routers.
To find the proper MTU Size, you'll have to do a special ping of the destination you're trying to go to. A destination could be another computer, or a URL.
1. Click on the Start button, then select the Run option.
2. In the "Open" field type in command (If you're using Windows 2K/NT/XP use CMD instead)
3. Once the window opens, you'll need to do a special ping. It should be formatted:
ping [-f] [-l] [MTU value] [Enter] an e... unfurl="true"]http://192.168.1.1/Filters.htm into the "Address" bar
6. You will be prompted for a User Name and Password. Leave the User Name blank and input admin as the password then click OK
7. Once you've done this you should find your self on the Filters tab. Scroll down to the bottom and look for "MTU". Enable the option and input the optimum value you got earlier. So for our example this would be 1480. After that value has been inputted click Apply then Continue and you're done.
NOTE: If you don't have a "MTU" option please goto
and select the model number of the router you have and the OS you're using. Then click on "Firmware" and follow the upgrade instructions.
