Business leaders and IT departments often clash when Network Security gets in the way of making money. Your objective as an IT manager is to protect the company from security threats. While the business leader may see you hindering productivity, you may see the business leader as a liability to your network.
So what do you do when you find this business leader circumventing your internet proxy using a site they found through proxy.org? You have a few choices. You could have that site blocked, which will solve nothing, since they will just find another proxy site to bypass it. You could tell that person's manager. (Oh my, let's not go there...) Or, why not find out why this user needs access to this site, and determine if this site should be available everyone at your organization.
Any network engineer can lock down the network completely to protect it with the right resources. Block the network too much, and you could reduce performance of your company and effectively shoot yourself in the foot. If you determine that the user has a business need to access the site, then your firewall team will need to determine if the site presents a security risk to your network. It isn't about boundaries, it is about good customer service.
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