Obstacles (and Potential Embarrassments) to Avoid When Cleaning Out Old E-mails


Q: I ran into a very embarrassing situation. I need your advice so I won’t face this problem again, and maybe it’ll be helpful to your readers, too. Here’s what happened: When I read your June 2009 column item “It’s Not Enough to Just Delete Old Messages in Outlook, You’ve Got to Compact” (page 88), I felt so guilty that I started to clean out the thousand or so old e-mails from my Outlook Deleted Items folder. I quickly learned that when I tried to erase too many in one fell swoop, my computer got very edgy and locked up. When I kept the group deletes down to a hundred at a time, deletions went smoothly, until I hit the send the receipt hurdle. It turns out my Deleted Items box had loads of messages in which the senders had asked for a receipt to show they were received and read. Well, I never read, let alone opened, many of those messages, but when I went to erase them, each one asked if I wanted to send a receipt. That caused repeated delays in my e-mail cleanup project. But since I figured the messages were being deleted, I took the easy path and OK’d the receipt. I learned later that loads of people received receipts months and years after they sent the original e-mails, and some even said I had not read their message. Ouch!


A: I get the picture, and I’m sorry you had to learn the hard way. Be aware that use of Read receipt or Delivery receipt is often iffy, to say the least. First of all, some network administrators quietly disable that service to lessen the load on the network, and if the original sender’s address changes, your undelivered receipt may hang about your system forever. Worse: Just because you get a Read receipt, that does not mean the message has been read—only that it’s been opened. Also requests for Delivery receipts are often spam, and the receipt is used to confirm that your mail account is still active.


But let’s return to the point of your concern. To avoid that problem in the future, you have two options: Either set your Outlook default to automatically send Delivery and Read receipts (which I don’t recommend) or set it to never send a response (which is what I do). To set the defaults, click on Tools, Options, E-mail Options, Tracking Options and click or unclick on the appropriate boxes (see screenshot below).



Now let’s return to your other concern. The best way to remove many old messages is to start from a certain date backward in time: Order the folder with newer messages at the top, select the message you want to start at, hold down the Shift key, then press End. This will select from the selected message to the bottom of the list. Then press the Delete key. The operation will take a minute or two. When you’re done, perform a Compact Now, which is described in the June column item.



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