Today, Microsoft Research published an interesting add-in that works with both Outlook 2007 and Outlook 2010 to help suppress the awful mess that users can get themselves into with the ‘Reply All’ button.

As you probably know, “reply all” works by creating a reply addressed to every TO: and CC: recipient in a message header (BCC recipients are dropped). When used correctly, the reply all function is valuable in terms of making sure that everyone on a message thread receives the latest contribution to a discussion.  The problem is that people get lured into a false sense of security that reply all is the way to respond to every message. They only learn the hard lesson that reply all can tell when they dispatch a message copied to all and sundry within the company (and maybe a few external recipients) to share some of their deepest and most private thoughts, such as what they really think of the CEO.

You might say, “but the user can rescue themselves by recalling a message sent in error” and yes, although Outlook provides such a feature, modern messaging systems are so fast at delivering messages and users are so wired and connected that it’s likely that the damage is done and the offending message is read a few seconds after it is sent.

Exchange 2010 attempts to solve the problem with “MailTips”. Essentially, MailTips are pieces of advice delivered by clients to users based on to whom they address a message. The data used by MailTips is derived from system data (such as the number of recipients in a distribution group) and personal data sourced from Active Directory (such as the fact that a recipient’s mailbox has exceeded quota and isn’t accepting any more messages).  You can also create customized MailTips for mail recipients – for example, to indicate that a distribution group is moderated and messages sent to the group won’t be distributed until the message is passed by a moderator.

The Client Access Server works with clients to figure out what MailTips to display and all is well as long as you use a client that knows how to request and display MailTips. The only clients in this category are Outlook 2010 and Outlook Web App (OWA), so you’re out of luck if you run Outlook 2003 or Outlook 2007 even if you’ve invested heavily to deploy a brand-new Exchange 2010 environment.

The add-in published by Microsoft Research isn’t a perfect solution. But that’s not surprising because people have all manner of bad email habits that won’t be cured with software. The important point is that it’s a help that may be appropriate and useful in your deployment, so it’s worth having a look to see whether it makes sense for you.

– Tony