Learn about the Microsoft Office Outlook Connector

The Outlook Connector enables two-way synchronization of e-mail messages, calendar items, contacts, tasks, and notes between Outlook and Windows Live Hotmail.

Note Calendar synchronization with Outlook is a paid, subscription-only feature. When you subscribe to Windows Live Hotmail, you get to synchronize notes and tasks as well as your calendar.

If you do not have a Windows Live Hotmail account, you can either sign up for a new account or update your existing MSN Hotmail account to be a Windows Live Hotmail account.

To update from MSN Hotmail to Windows Live Hotmail, click the Join Windows Live Hotmail link when you log on to your account. All of your messages, folders, and contacts will automatically appear in your new account. Your e-mail address will not change.

Download and install the Outlook Connector

  1. Exit Outlook.
  2. Download the Microsoft Office Outlook Connector.
  3. When prompted to open or save the file, click Open.
  4. When prompted to run the software, click Run. Note You may see a security prompt, depending on which operating system or Web browser you use. If you see such a dialog box, you must click the option to continue with the installation.
  5. Follow the instructions on your screen to complete the installation.
  6. The next time you start Outlook, you are prompted to configure the Outlook Connector. Enter the following information:
    • Your e-mail address
    • Your password
    • Your name as you want it to appear in the receiver’s Inbox
  7. Click OK.Microsoft Office Outlook Connector account configurationAfter Outlook opens, your Windows Live Hotmail account appears in the Navigation Pane (Navigation Pane: The column on the left side of the Outlook window that includes panes such as Shortcuts or Mail and the shortcuts or folders within each pane. Click a folder to show the items in the folder.).New account folders appear in Navigation Pane

Learn why I must type characters from an image when sending e-mail messages

The Outlook Connector uses a Human Interaction Proof (HIP) challenge. A HIP challenge uses an image or audio file containing characters that are decipherable only by a person. This requirement confirms that a person, rather than an automated program, is trying to send an e-mail message. This helps prevents automated programs from misusing the Windows Live Hotmail service.

On occasion the HIP challenge will appear after you send an e-mail message with your Windows Live Hotmail account.

Note There might be a delay of a few seconds or longer before the HIP challenge appears. If the message you are sending is not in your Outbox but is in your Sent Items folder, then your message has been successfully sent to the Windows Live Hotmail server.

Outlook Connector HIP challenge

If the HIP challenge appears, you must type the numbers and letters you see in the picture to continue sending the mail. If you mistakenly type an incorrect character, you will be asked to type a new set of characters. Look at the numbers and letters in the picture, and then type them in the box below the picture.

If you are unable to see the image, click the audio icon Button image . The characters in the image are replaced with an audio icon.

HIP audio challenge

Click Play Audio to hear an audio recording of characters.

If you can’t read and hear one or more of the letters or numbers, click Button image to get a new set of characters.


  • The audio version might seem faint or mixed with background voices and noise. This is intentional to ensure a person, not an automated program, completes the HIP challenge.
  • The letters are not case sensitive. The capital “A” and small-case “a” are considered the same character. There are also no spaces between the numbers or letters.

(Originally on microsoft.com)