<p>Realistically - </p>
<p>(Many) companies can and do monitor (to some extent or fully when requested) company email - i.e. email at company.com. They also generally retain all emails, virtually forever now, in order to make sure they met any compliance directives. Of course the extent varies with the particular company.</p>
<p>Also, (many) companies direct all internet bound traffic from the company’s network through a proxy server of theirs which is sort of a central gateway to the internet. They can monitor whatever they want at this level but more typically would use it to block access to certain websites and possibly monitor the websites to make sure they’re appropriate. They also usually block incoming spam.</p>
<p>(Most) companies would not monitor email at private email locations (gmail, hotmail, etc.) even when using company PCs since it’s a much bigger deal to capture the packets and peruse those than to review what’s on the company email. Of course, they might choose to do this even though it’s a big pain. </p>
<p>I think most companies would not use a key logger since that can generate a huge amount of data to have to review and sometimes they wouldn’t want the reviewers to see the data for every employee - for example the CEO or other executive’s keystrokes. They might, however, use it if they felt there was a true need. When they use a key logger app they could see every single keystroke.</p>
<p>Generally, if one is using a company laptop at home while not connected to the company’s network via VPN the company wouldn’t see any of the internet traffic including emails to gmail, hotmail, etc. or postings to CC. However, browsers cache a certain amount of pages, pictures, etc. and keep a history of the visited sites. These can usually be deleted though through settings in the particular browser but otherwise, if the company had access to the computer they can see it.</p>
<p>Many companies have their computers configured so that the IT department has administrative rights on it when connected to the company’s domain. When configured this way, an IT person can simply log on to your computer and see anything that’s there (as long as the computer’s connected to the domain - which it wouldn’t be if used at home and not VPN’d in).</p>
<p>All of the above is ‘generally’ since there are always exceptions.</p>
<p>The best bet is to simply not do anything inappropriate with the company computer while at work with ‘inappropriate’ meaning that you wouldn’t refrain from what you’re doing if your boss was standing behind you, or any co-worker, or the CEO, or your mother, or your kid and not do anything you’d have to try to defend in any way to your management (going to inappropriate websites, spending too much time on the internet that’s non-business related ).</p>