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Outlook Lists: Unexpected Behavior Problem

We ran into a problem recently in Outlook which has given me a new "pattern" I want to think about more. Here is the basic problem.
  1. Outlook stores the addresses from email messsages one "bucket" which it uses to autofill the TO field in new messages.
  2. There is a different "bucket" which contains all of your contacts.
  3. It makes sense that these "buckets" are seperate since you send and receive emails to and from more people than are in your contact list and it's nice to have those autofill when you are corresponding.Its like having a public area for the masses and then a subset of those emails which is private and includes friends, family and associates.
  4. There are ways of moving information from the autofill bucket to the contact bucket by right clicking on the address in the TO field and choosing ADD TO CONTACTS. This moves from public to private.
  5. It's also makes sense that your contact list should show up in the autofill. If contacts is a subset of everyone and everyone is in the autofill then contacts should show up in the autofill.
What about deleting? This where we ran into our problems.

One of our staff created two distribution lists in her contacts. They had similar names (which might not be the best practice but that isn't germane to our discussion). After a while, one was no longer needed and she deleted it. To follow the same mental framework from above, she deleted it in the "private" area. This however, left it untouched in the "public" area.

The next day, unbeknownst to her, she sent out a 300 person email to the wrong distribution list. This was because the "wrong" one, the one she deleted, still came up in the autofill area. However, since it didn't appear in her contact area, she didn't even know she needed to be on the lookout for such a problem. She (naturally) assumed it was gone. In fact, the only way we determind what had happened was after an hour of sleuth work was to start to type in the autofill and could the number of options which appeared and compare it to the number of options in her contacts. When there was an extra one in the autofill, we figured out what had happened. As you might guess, that was not our first action.

I like the two bucket approach but perhaps there needs to be tighter integration.

Possible Patterns to make this more user friendly
  1. When something is deleted in contacts it is deleted in the autofill (but not necessaruly vice versa)
  2. When deleting, present an option to delete in autofill as well.
  3. Have a more visible way of editing your autofill list. Currently, I don't believe there is any way to view the list of emails in the autofill, let alone edit it. I don't mind this being hidden and the autofill happen "by magic" by in situations like this it might be better to demystify it.
Random thoughts from a tech incident.
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