Helping people with computers... one answer at a time.
When sending email on a company owned computer or using a company owned network, the company can watch. They can likely read your email and much more.
If I send an email on my work computer through Hotmail, will it be picked up on the server that has been set up in the office to hold all emails sent through on our "actual office computer emails' via a paying service provider?
In other words can the email I've sent be read afterwards on the office server or at the office's service provider if it has been sent through Hotmail?
The specific answer to the specific question you're asking is: No.
But that doesn't mean your email couldn't be read by your company in other ways.
In which case the answer the question you're really asking is: yes, they might be able to read the mail you sent.
When you send email using Hotmail, either through Hotmail's web interface, or when supported, through a mail program like Outlook or Outlook Express, the mail is not sent using your company's mail servers. It's sent directly to the Hotmail mail servers, and from there it moves on to its final destination.
So your company's mail servers are never involved.
But while that might give you some level of comfort, you shouldn't read too much into it. Your company could still be reading your email.
Before I throw out the possibilities, though, I want to make something clear: I'm not saying that your company is reading your email. In fact, it's more likely that they are not. But they could, both legally and technologically. And that's something you should be aware of.
When you use a computer at your work place, that computer belongs to your company. They can do whatever they will with it. And that includes, for example, installing spyware as either software or hardware to monitor your activities. That spyware could easily be logging every website you visit, every mouse movement you make and every keystroke you type. Put that all together, and they could absolutely track what you were typing as you composed a new email when you visited Hotmail - or any email provider for that matter.
This includes the email you typed up but never sent.
What if you're using your own computer? You have a little more security, in that you can (and should) take absolute care to ensure that your machine is protected, firewalled and spyware and virus free. But that may still not be enough. For example it's quite possible that monitoring software can get installed as part of your corporate network login.
Even if your computer is clean, you're still using your company's network, and your network traffic can be monitored. Unless you're using a secure connection via HTTPS or a secure email protocol, it's trivial for your company to record all data sent to and from your computer, including any email you send.
If you use a secure connection you've made it a lot harder (though actually not impossible in a corporate environment) to monitor your traffic.
If you're truly concerned that you might be spied on, assume the worst and take the appropriate steps to protect yourself.
If you want to send something that you don't want your company to see, you simply shouldn't be doing it from their network or on their equipment. Wait 'till you get home or are somewhere else using equipment that your company has no control over.
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