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E-mail that goes to my outlook.com e-mail address drastically changes the ads I see all across the web. However, if I access the site via a privacy window that destroys all cookies, my advertising isn't immediately targeted exactly at me.

I do not get the same from gmail or yahoo, only from Outlook, and literally, it is instantaneous in how ads convert.

By the by, I use outlook.com for any ‘public’ e-mail signups - store rewards, picture e-mails from promotional events, etc. So if I access outlook.com with a browser, then visit anywhere else on the web, I suddenly switch over to ads for competing stores, Disney vacations, etc. Clear the cookies, and the ads go away until the next time I forget and access Outlook.com on an open browser window.

Your mileage may vary, but having had the same yahoo e-mail address for 11+ years and the same gmail address since the beta, I've never experienced such a dramatic shift in ads until I used outlook.