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Our firewalls here at work block traffic to a number of websites, even though there is no official policy against using them (the lawyers said "block these" so we did).
Anyone found bypassing the blocks would be penalized under the "circumventing or bypassing network or software security devices, or accessing unauthorized network resources" clause in our employee AUP. Depending on what they access and how many times they do it, penalties range from terminating Internet access at their workstation to the termination of their employment.
Oh, and Hotmail is probably blocked because it's been used as a vector for a few computer worms recently. The last time I checked, Microsoft still didn't virus scan attachments worth a cr*p, and Hotmail is a great resource for getting virii into a lot of mailboxes in a short period of time. It doesn't help that, for the longest time, Hotmail had (still has?) the ability to autolaunch attachments on the client computer with a simple doubleclick. We don't block it here, but I understand that many people do.
If your GF needs Hotmail access without port 80, tell her to check and see if she has Outlook Express on her PC (most Windows boxes do). Outlook Express has the ability to retrieve email from Hotmail without using the web, which should get her around the block without technically "bypassing" the block. If her IT department is so paranoid about security I'd assume that she's already on a patching schedule and has a local AV solution, so she SHOULD be protected from worms. Still, keep in mind that she will probably be held liable if her email allows a virus onto her computer, which jumps to the network. At a minimum that could get her fired. In some states and with come companies, that could get her sued for the cleanup costs.
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