I regularly send emails to multiple recipients with Windows Live Mail and it’s tiresome to have to manually select their email addresses from the contacts database each time. Is there any way I can add their details to a group, which can be used to contact them each time?

This can be easily done in Windows Live Mail, although the software calls groups ‘categories’. Click on Contacts in the bottom left of the main Live Mail window to bring up the Windows Live Contacts. It can also download your contacts list from Windows Live Messenger or Hotmail.

Click the arrow next to New, then from the dropdown menu, click Category. In the window that appears, give the category a name and choose which people in your contacts list you would like to add to it. People can belong to more than one category. Their names will appear at the bottom. Click on Save when you’re happy with the selection.
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Now close the contacts list and return to the main Windows Live Mail screen. Click New to begin writing a new email. Either type the category name in the box labelled ‘To:’ or click the ‘To:’ icon and select the category from your contacts list.

Email addresses can be added and removed from the category as needed. Open the contacts list in the same way as before, right-click on the category and click edit category.

Be careful though, as any changes you make in Live Mail will be carried over into Messenger and Hotmail, including deleting a contact and creating a group. If you create a group in Windows Live Mail, it will also appear in Messenger. You probably won’t be able to get an insurance quote to protect you from that sort of thing 😉