Can a file transfer to a USB pen drive be tracked in windows 7?
Technically, if it is the company's computer, they have the ability to track your every movement, if they want to. This doesn't mean they do, just that they could. My recommendation is to check with your manager or whoever is in charge and see if they mind you doing it. If there are no bad intentions, then they might give you permission to do it.
Using group policy, your machine can be configured to not allow USB drives or other sorts of revmovable memory devices. The use of such devices can also be tracked.
There are also many network management tools that allow the blocking and tracking of all that goes on on the office computers.
If it is against policy, there are probably allowed exceptions, and if your need is as innocent as you claim, there should not be an issue.
The thing to remember though is that these are not your computers, they belong to the company, and the company has the privilege of deciding what does and does not occur on those computers, and the operating systems of today offer your company vast and powerful tools for ensuring you do not act against policy and that if you do, they are informed of it.
UPDATE response to comment: Group policy and any good monitoring tools will report whether the LAN is connected or not. They will simply save the logs until when they can transmit them back to the administrators.
Your best option is to talk to your supervisors. Any good sysadmin will not be fooled by your methods of circumventing their protections, and even if you successfully hide what you're doing, the fact that you're hiding it will probably not remain hidden and will raise suspicions on it's own. Let your supervisor know, then when IT asks why you did what you did, your supervisor will be able to tell them it was with his permission.
A good sysadmin will find out. You should work within the structures defined by the business unless you really don't care whether or not you get fired.
I am using my own keylogger (just simple AutoIt script) which track not only the keypress, but also every change in active window title. I tried copying bunch of files, and yes, they do show up in my log. So, technically, it is very easy to track whatever you do, including using the flash drive. I know your pain, I live in Indonesia where even a 60 kBps (note the B) is a very good speed for average home user. Sometimes I deliberately come to the office at night and initiate a huge download to take away in the next morning. But, I did it because the admin allows me. Do check the policy of your office about this. If they buy an internet package with limited quota, whatever you're downloading outside your job is freeloading, which the admin probably won't like, much less your manager. However, if the video you're downloading will increase your job productivity, or better, can be shared with your coworkers to increase their productivity, I see no reason why a short chat with upper management won't give you the access
Simply put, yes.
More:
Hak5, a great tech video podcast, did a small segment once about how Windows keeps a log of all USB devices ever connected to a computer. You can watch it here: http://hak5.org/hack/usb-device-tracking
So regardless of whether your company is actively trying to track/block USB devices, which they very well might be doing, Windows takes care of the tracking all by itself. Yes, the video references Windows XP but as far as I know this also exists on Windows 7. If someone can verify that would be great!