Hi Nate! It sounds as if you may have inadvertently blocked that particular user's address. Assuming you're using 2010 Outlook and also assuming the email is in your delete folder, right-click on the email and select "Junk" and then "Junk E-mail Options." Choose the Blocked Senders tab, find the email address you want to allow, and then select remove. You can also right-click on the email and select "Junk" - "Never block sender." Hope this works for you.