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common outlook mistakesIf you work in a typical office environment, the odds are pretty good that the mail system is an Exchange sever and that the mail client of choice is Outlook. We’ve covered Outlook here at MUO from a few angles, including Outlook Journal Track Emails, Phone Calls, And Tasks With Outlook Journal Track Emails, Phone Calls, And Tasks With Outlook Journal Since Outlook is about as common as Word and Excel on most work computers around the world, I'd like to share with you a few tips about how you can use the really cool Journal... Read More and backing up your Outlook data 5 Easy Ways To Back Up Your Microsoft Outlook Data 5 Easy Ways To Back Up Your Microsoft Outlook Data Read More . We even covered some cool VBA scripting in Outlook where you could export your tasks into an Excel spreadsheet How To Export Your Outlook Tasks To Excel With VBA How To Export Your Outlook Tasks To Excel With VBA Whether or not you are a fan of Microsoft, one good thing that can be said about MS Office products, at least, is how easy it is to integrate each of them with one another.... Read More .

In this article, I’m going to take a closer look at the Outlook client itself and a few of the common Outlook mistakes that people often fall victim to. Luckily, there are a few built in tools that you can use to try and safeguard yourself from making one of those mistakes at work that’ll take you a long time to live down.

What are some of those mistakes? How about hitting “reply all” to one of those mass emails and making a complete fool out of yourself? How about writing something quickly in the heat of passion to your boss that you completely regret the moment you click on “send“? There are so many situations that people out there that can relate to these sort of situations, and lots of people have their own email horror stories. So, it makes sense that Microsoft would embed a few important tools to help guard against those common Outlook mistakes.

The Dangers Of Email

There are three email dangers that I’m going to cover in this article – sending out that email that you regret the moment you send it, sending an email to the wrong person, and finally that old reply-all mistake that so many people are guilty of.

The Email You Regret Sending

You know what, we all have those days. You get yet another email from a boss or colleague that just rubs you the wrong way. You’ve had a bad morning, or you didn’t finish your first cup of coffee yet, and so you hit reply and just unleash all of your frustration and anger in one, horrible email.

5 minutes and several curse-words later, you finish that email and with barely a pause, you click on “Send“. Then, after sitting in smug satisfaction for about three or four seconds, it begins to dawn on you exactly what you’ve just done – and the potential consequences. You realize, with a sinking feeling your stomach, that you really shouldn’t have sent it.

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Have no fear, Outlook comes with a very cool tool just for this sort of thing – except you have to do it on your client before you make this emotional mistake, not after. I call it the “email-delay insurance”. To enable it, just click on “File”, “Info” and click on “Manage Rules & Alerts“.


Basically, what you’re going to do here is create a rule that delays all of your outgoing emails for 5 minutes. This gives you a little bit of “cool-down” insurance, so that you can prevent those mistakes from happening before they happen.

On the E-mail rules screen, click on “New Rule…

Then click on “Apply rule on messages I send“. This will apply the delay to every single email you send the moment you click on the “Send” button.

common outlook errors

On the next step in the Rules Wizard, you have the option to limit the number of outgoing messages this applies to. For example, it can be only important messages, or with certain words in the body of your message (maybe checking for certain choice curse words you like to use?)

In this example, I’m going to just apply it to all outgoing messages, so you click next, and then just click on “Yes” for the warning message.

common outlook errors

Finally, select “defer delivery by a number of minutes“, click on the “a number” link, and set the delay period to whatever amount of time you think it’ll take you to cool off and cancel the message before it actually gets sent.

common errors in outlook

On the final step, you can apply exceptions to this rule so that it won’t delay messages sent to certain people (as one example). For example, I know that I can pretty much write anything at all that I want to my buddy John, and he won’t get angry with me. We’re best buddies after all – so I’m going to make an exception for those messages with his email address in the “recipient” field.

common errors in outlook

Name your delay rule, and you’re good to go (don’t forget to turn on the rule).

common errors in outlook

Now, every time you send out an email, it’ll sit in the outbox for 5 minutes. So, if you decide after a minute or so that sending the email was actually a huge mistake, you can go into your outbox and delete the message – and avoid  a major crisis.

Verify Who Your Message is Going To

There’s a common mistake people make when quickly sending emails out to people – you’ve probably experienced it yourself. You go to send an email to a friend named, say, Ryan Dube for example. So you type in “ry” and three matching names from the Exchange server global contact list or from your personal contact list come up.

Because you’re in such a hurry, you accidentally select “Bryan Dube“, and proceed to write about your weekend escapade in Vegas. You carefully detail all of the things you did there – you know, all of the things that were supposed to stay in Vegas? You click “Send“, open your “Sent” box to make sure it went to  your buddy okay, and then it dawns on you that you sent it to the wrong person. Even worse – Bryan Dube happens to be the Company President that had sent you some mass email last week (that’s why he showed up as a drop-down contact).

Yeah, that’s called being screwed.

Instead, make use of a little pro-tip known as Control-K right after you type the first couple of letters of your  friend’s name. This opens up the “Check Names” tool and lets you actually select the person’s name from the official contact list. 

This may feel like an extra step at first, but for those particularly sensitive messages, it’s a very important extra step. It lets you confirm and ensure that the message your writing is going to the correct person.

Let MailTips Alert You of Common Outlook Mistakes

Personally, I think MailTips is one of the greatest inventions ever built into Outlook. MailTips protects you from a long list of issues by warning you about things like whether the recipient you’re sending an email to is actually a group with a large number of recipients (which will protect you from the reply-all mistake), whether you’re sending an email to someone outside of the company, and similar informational tips.

To enable MailTips, just go into Outlook Options, select “Mail” and then scroll down until you see the “MailTips Options” button. 

You’ll see all of the things that MailTips does for you in this Options box. If you like everything you see, confirm that “Display automatically” is selected and then click on OK.

MailTips can really be a lifesaver. When critical emails roll in, you’ll get tipped that this is one you may want to respond to. It also tells you if it has come from an automated system that auto-forwarded the email to you – a nice feature for IT folks that have set up auto-forward rules from different scripts that monitor computer systems and servers.

MailTips will also advise you when you’re trying to send an email to an invalid email address, or to an address that contains a huge number of recipients. MailTips can save you from making common email mistakes in far too many ways to list here.

Just using these three important pro-tools in Outlook could save your life – or at least your pride. Enable them and use them, and save yourself the headache of making these common Outlook mistakes. It might even save your career!

Have you ever made any embarrassing email mistakes where tips like these would have saved you? Share your experiences in the comments section below!

Image Credits: Distressed Woman Via Shutterstock

  1. Russell Smith
    March 14, 2013 at 8:29 am

    There are many points discussed in this post to avoid common mistake. I would like to add an another point which is related with duplicate copies of mails items repeatedly. If you use Outlook then is you are getting duplicate copies then "Leave a copy of message on server" otherwise your mailbox will get flooded with redundant items.

    If same case happens in your case then disable this option. However you can use Outlook duplicate remover software that delete all duplicate copies. You can check demo of this duplicate remover utility from :

    Regards :

  2. Prashant Mirjankar
    March 13, 2013 at 5:53 am

    thanks for sharing these wonderful tips.... just recently started using outlook.

  3. dragonmouth
    March 8, 2013 at 5:45 pm

    I know that the title says "Outlook" but can rules be set up for other mail clients such as GMail? I'm specifically interested in the Delay Rule. From what I saw in GMail Settings, it doesn't look like a delay can be set up.

  4. GuyMcDowell
    March 7, 2013 at 1:48 pm

    I never thought of applying rules to outgoing e-mail. By making one with a list of common curse words or coarse language, perhaps you could foil someone who might get a hold of your account.

    Ctrl-K is very handy too. Every now and again, I like to delete addresses from the auto-suggest box to help minimize the mistake of sending to the wrong person.

  5. Faizaan
    March 7, 2013 at 1:43 pm

    Very Very Useful.
    Thanks a lot.

  6. cypherinfo
    March 7, 2013 at 12:05 pm

    Hello, a better and efficient way to undo an already sent e-mail message is to add (via local or web app) a functionality to delete that message. What about all of the free tools to do that? Thank you.

  7. Mohammad Wasiullah
    March 7, 2013 at 11:13 am

    Thanks very useful information

  8. Nevzat Akkaya
    March 7, 2013 at 7:30 am

    Great tips, thanks Ryan.

  9. lhamil64
    March 7, 2013 at 3:09 am

    Another annoyance I had with Outlook was that it defaulted to my Gmail account, so I kept sending email from there when I meant to send it from my school email. The solution I found for this was changing a registry value to force account selection every time you make a new email (but it still works fine for replies and forwards without prompting). Basically, just change the key:
    ForceAccountSelection from 0 to 1 for force selection.

    For Office 2013, the key is:

    I'm assuming for an older version you just need to find the key for your version.

  10. Drew Marigomen
    March 7, 2013 at 2:23 am

    Setting up rules in Outlook helps me organizing emails.

  11. Eileen Souza
    March 7, 2013 at 12:22 am

    Thank you for these great tips. While I have lots of rules for incoming mail, I never considered setting one for outgoing. Good one!

    I like the concept of MailTips. I use Outlook 2010 and MailTips is not an option for me under Mail. I do not use an Exchange server. Is this feature only available when you use Exchange?

  12. Garris Rago
    March 7, 2013 at 12:16 am

    I'm going to get outlook just for these tips. I had no idea these things were available, thanks so much for this article!

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