A reader of this blog recently emailed me to ask:

What s/w do you recommend to keep anonymous while using Gmail, IE, Outlook, and Facebook on a laptop?

This is actually a very tricky question because the nature of all of these tools, except Internet Explorer (IE), is to be associated with a visible and discoverable account and identity in the "cloud". I will discuss IE last and separately.

Gmail ties to your gmail and other Google accounts. Outlook ties to some existing email account at some email provider. Facebook is tied to your Facebook account and is explicitly designed for making your information public.

The profound question here is, what do we even mean by being anonymous using these services? I would argue that the best one can manage is to be pseudonymous; that is to maintain a persistent and visible pseudonym / alias which, while discoverable, is not associated with your true identity.

Fortunately Gmail and Facebook are free and typically do not require any real credentials to set up an account, and many of the free email providers work similarly. Using Anonymizer Universal (AU), and a browser with no history or cache to set up the accounts would ensure they were not connected to your real identity. It is important that the accounts never be accessed in any way except through AU, or they will be forever after associated with your real IP address. Furthermore, it is critical that the browser used is never used for any activity connected to your real identity, or the cookies and other digital detritus in your browser may allow these sites (or other folks) to tie the pseudonym to your other real name accounts.

IE is in many ways the easiest because there is no underlying account, but all the same rules apply. You need to ensure that you isolate your anonymous or pseudonymous activity from your real name activity.

For all of this activity a virtual machine can be a very effective tool. For example, if you use a Mac you can use a virtual machine running Windows or Linux for all of your alias activities and use the normal operating system for your real name activities. Similar tools exist for other operating systems.