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I check email on the same computer in the same location using Outlook or webmail (web-browser). My webmail logged and showed the current and the last login IP. If I check my email by Outlook then later by webmail, I would see the two IP addresses are different. What is the reason for that?

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How is Outlook configured to reach your Exchange server? RPC over HTTP perhaps? Do you recognized either of the IP's? Are you checking from the same computer each time? Are you (or your router) on a dynamic IP? –  Ƭᴇcʜιᴇ007 Jun 2 '12 at 20:06

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Possible reasons include

  • you are using a proxy in your browser
  • HTTP traffic is sent through a proxy somewhere else (company network?)
  • your ISP uses dynamic IP assignment and your address changed between these two attempts
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Or the org has many Exchange servers on different networks, and you address appears different because of the different routing. –  Zoredache Jun 2 '12 at 9:59

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