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(Remember—the originals already exist somewhere else.) If you need to save sent messages, consider how long you need to retain them, then sort the mailbox by date and use the range selection method above to easily delete messages that are no longer needed.
After attempting the solutions below, if you find you are still receiving an "Over Quota" warning, please contact the Help Desk and to increase your quota.Although most people prefer to clean up each folder individually (see the next suggestion), a more general clean up can be done by using Find items older than [xx] days or Find items larger than [xx]MB.(And after using one method, use the other.) When the list appears, review it and move critical emails to another folder before clicking Edit, Select All, then hitting the [Delete] key.(And really, how many photos of Grandpa Bill and the kids do you need?) To get rid of an attachment and its message, just delete the message.
The default column that Outlook sorts by is "Received", but you can also sort by "From", "Subject", "Size", or whether the message has an attachment that you might want to save to a local or network drive.