Twitter follower Jason Verly is interested in learning my technique for auto-filtering email. When I mentioned that doing this requires Outlook he didn’t shy away.
The two key components are Outlook and Stairways Software’s $36 Keyboard Maestro. The latter is an outstanding macro program that I use to fire off a series of Outlook commands.
I use this technique to handle the scads of PR releases I receive each day. In general terms, it allows me to add a sender to Outlook’s contacts and then assign a specific category to that contact. When future messages from that sender arrive, they are moved to a specific folder via a rule I’ve created within Outlook.
The Category feature is key here, and explains why I stick with Outlook though I’m not otherwise thrilled with it. Mail doesn’t offer categories (nor do any Mail add-ons I’m aware of) and therefore makes this kind of workflow impossible. Now, to the specific steps.
Launch Outlook and from the Message menu choose Categorize > Add New. In the sheet that appears enter a distinctive name for your category. In my case I call it Marketing. Now in Outlook’s list of email accounts Control-click (right-click) on the account that receives this email (mine would be Macworld) and choose New Folder. Give that folder a distinctive name—I call mine PR Releases. If you now select Messages > Move you should see that folder’s name in the submenu.
Launch System Preferences > Keyboard and click on App Shortcuts. Click the plus (+) button at the bottom of the shortcuts pane and in the sheet that appears click on the Application pop-up menu and navigate to Microsoft Outlook (choose Other and then navigate to it if it doesn’t appear among the menu’s choices).

Assign keyboard shortcuts to Outlook in the Keyboard system preference.
In the Menu Title field enter Add to Contacts
. In the Keyboard Shortcut field, enter a shortcut of your choosing—Command-Option-A, for example. Click the plus button again and, with Microsoft Outlook showing in the Applications menu, enter Marketing
in the Menu Title field and then enter a keyboard shortcut—Command-Option-M, for instance. Finally, create one more Outlook shortcut. The command field will contain the name of the folder you created and its account—in this instance it would be PR Releases (Macworld). Assign a keyboard shortcut—I use Command-Option-right arrow.
Now return to Outlook and choose Tools > Rules and select the account that receives the messages you want to filter—I’d choose my Macworld account, but you may want to select a Google or iCloud account, for example. Click the plus button to create and configure a new rule. Mine looks like this:

A rule like this takes care of any future messages from categorized contacts.
Many of the pieces are in place. I’ve created a specific category for the messages I want to filter, assigned keyboard shortcuts to the commands I need, and designed a rule that will move any future messages from these senders to a particular folder. Now it’s just a matter of configuring the macro. It looks like this:

Finally, Keyboard Maestro fires off the series of shortcuts necessary to deal with the selected message.
The gist is that I create the macro, assign a keyboard shortcut to it, and then lay out this series of actions, which trigger keyboard shortcuts within Outlook that do my bidding. Specifically the actions do this:
- Make Outlook active.
- Add the selected message’s sender to Outlook’s contacts.
- Assign the Marketing category to that contact.
- Close the contact window.
- Save the contact.
- Move the selected message to the PR Releases folder.
Phew. Done. Now when I receive a PR pitch from a new contact I simply invoke the macro with a single shortcut. In seconds they’re properly categorized and their message is moved to my PR folder. And if a message arrives from a sender who’s already been categorized, their message automatically moves to the PR folder thanks to the rule I’ve created. While the initial setup can be a little taxing, the reward in not having to manually move messages and assign categories is well worth the trouble.