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Browser Extras

ieHTTPHeaders
This is an explorer bar add-on that exposes the HTTP headers Internet Explorer is sending and receiving.
Source Tree
This explorer bar add-on lists all the external script and css files available in the source (with some exceptions). No more viewing the source, copying the location, prepending "view-source:" to it and putting all of that in the address bar to view external files.
ieDocMon
From the same guy that developed Source Tree, this explorer bar add-on lets you view partial source of nodes, watch one, some, or all events on one, some, or all nodes in the document. It will even highlight selected, visible nodes. Very useful as a debugging tool.

Email Extras

POPFile
Using Bayesian filters, POPFile has helped me practically eliminate the spam that reaches my inbox.

Utilities

AnalogX
There are a ton of really useful little programs available at this site. A couple of my favorite are the Internet Traffic Report client and Netstat Live.
SpaceMonger (v1.4.0)
There is nothing more frustrating, at least to me, than having a disk that seems to be bloated, but not having any idea where the fat is. This little program gives a highly intuitive visual look into the folder and file makeup of a selected drive.