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I have some problems with my manager and am in process of using a lawyer to litigate with regards to workplace harassment. The litigation is planned to be "soft" and my lawyer only plans to send the employer an email saying that he has heard cases of workplace hostility from me according to which I am seeking a constructive dismissal and claiming a reasonable severance. I am concerned that the employer might react aggressively and retaliates by looking at the logs of my computer to see if it can accuse me of theft.

I have transferred some of the files which I was working on (non are highly top secret - I am a designer) plus some personal files such a benefit claims and bank statements and pictures to Dropbox and a usb drive. I have deleted all my web browsing history. I have taken the files only to make my portfolio for future job searches, I had already discussed with my manager about how I can show case my work for future employers.

Can they track if data was uploaded to drop box? Can they detect what data? Same question for USB key, I already know they can track the USB, but can they detect what files exactly, in other words can they accuse me for taking my music files?

  • How should be know if "they" can? But yes, if prepared beforehand, every mouseclick, keystroke, screen content etc. of you can be logged. – deviantfan Nov 8 '16 at 2:27
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If you are using a computer provided by, controlled by or just even accessed by your employer (as almost everybody does at work), then the answer is yes, your employer could potentially log what you are doing.

When they have full control over your computer there is no limit to what they could log - screenshots, keystrokes, network traffic, etc, etc - and there is no reasonable way for you to find out.

However, if you are not working with something sensitive surrounded by high security, it might be unlikely that your employer has gone through the effort to log these things. What they are most likely to have is perhaps logs of your network traffic, e.g. your HTTP requests (but probably not bodys since they take a lot of space). In these filenames of files uploaded to dropbox might be found. (And yes, even if you used HTTPS your employer could get around that with an installed root certificate.)

So the answer is possibly, but you can not know for sure.

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