Your mail program appears to be configured to "leave mail on server" and to be forgetting when it last connected to pick up mail.
Usually pop clients delete messages as soon as they have successfully downloaded them, but sometimes you want to leave them on the server, eg when you are away from home, using someone else's computer to check your mail. (We would reccommend you use webmail to do this BTW)
To check the settings in outlook go to Menu Tools / accounts / (chose the account ) / properties or change / More Settings / Advanced
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