Q: How can I prevent valid email messages from going to Outlook's Junk E-mail folder?

A: Microsoft Outlook has a good built-in junk mail filter, and it's made more effective with some user input, so Outlook does a solid job of maintaining an Inbox free of time-wasting spam messages. But sometimes valid messages make it through to the Junk E-mail folder. This problem can happen after Microsoft releases an update to its junk mail filter that includes some subtle change.

I had this problem happen to me recently. I subscribe to an excellent, fairly busy Active Directory email list (activedir.org). Outlook started moving some of the messages from this list to my Junk E-mail folder. The recipient address, in the To field when I receive messages from the list, is always [email protected]. The sender address, in the From field, can be any of the many users subscribed to the list.

This problem is really simple to fix, of course. In Outlook 2010, I can navigate to the Junk E-mail folder, right click the message I'm interested in recovering, and select Junk from the context menu. As Figure 1 shows, I can tell Outlook to Never Block this Group or Mailing List.

Figure 1: Context menu options for junk mail control on a message

The resulting Add to Safe Lists dialog box, which Figure 2 shows, lets me tell Outlook to always trust messages for this mailing list.

Figure 2: Adding an email address to a safe list in Microsoft Outlook

When I select this option, Outlook returns this message to the Inbox. In this example, because the sender could be any one of thousands of list subscribers, it would be tedious to use the Never Block Sender option for each one (adding them to the Safe Senders List).

Now here's the annoying part about safelisting: When you tell Outlook that a message in the Junk E-mail folder isn't really spam, thus moving it back to the Inbox, there's no mechanism to automatically apply that preference to all other similar messages in the folder. When you create a new Outlook rule that affects inbound messages, there's a great option to apply that rule to messages already received, but there's no corresponding functionality for safelisting.

In my example, I had dozens of messages for the Active Directory list that had gone to my Junk E-mail folder. I safelisted the recipient address, but I still had to filter the folder for these messages and move them manually back to the Inbox. When you tell Outlook that a message isn't junk, your choice applies to future messages with the same property. All other similar messages in the Junk E-mail folder have to be manually screened and moved if desired.

See also, "The Implications of Outlook 2013 Changing OST Cache Behavior" and "Outlook 2010: Move MailItems After Sending."