Make Email Less Dangerous

It is too easy to do and it happens all the time, most recently in a headline-making gaffe from Uber. You realize, too late, that you sent an email to the wrong recipient. In your personal life, this can be embarrassing. In a law firm it can result in inadvertent disclosure that no disclaimer can protect from, especially if the unintended recipient is not a lawyer. Law firms have made headlines for accidentally leaking client secrets to the Wall Street Journal, and for using “reply all” to a distribution list that included reporters.  It can get worse, like in CRIT Corp/Peoplelink vs. Barns & Thornburg et al and Terraphase Engineering, Inc. v Arcadis, U.S., Inc, where errant emails were the cause of malpractice claims, counterclaims, and breach of fiduciary duty. Fortunately, there are quite a few ways to reduce these risks!

Turn off Autocomplete in Microsoft Outlook and Gmail

The auto-complete list is a feature which displays suggestions for names and email addresses as you begin to type them. These suggestions are possible matches from a list of names and email addresses from the email messages you have sent/received, not just those in your address book. By default, this feature is turned on in Outlook.

To turn off Auto-Complete List name suggestions in MS Outlook:

  1. Click the FILE tab.
  2. Click OPTIONS.
  3. Click MAIL.
  5. For extra security, you can also click the button “Empty the Auto-Complete List”.

Remove a name from MS Outlook Auto-CorrectIf you don’t want to turn off Auto-Complete at the least when you are typing someone’s name and see an old email address crop up along with a new one, or you only see the old one, click the “X” to the far right of their name/email address to remove just that email address from the auto-complete list.

In Gmail, there is no equivalent way to turn auto-complete off, but you can edit a contact’s information, essentially editing autocomplete function for that user:

  1. Log into your Gmail account
  2. Click the 3×3 grid in the upper right corner, and select CONTACTS (you might have to scroll or hit MORE first).
  3. Click the contact you want to edit and select the pencil to the right of the name.
  4. Click on the contact’s email address field. Once you click in the text box, an X icon shows to the right. You can either edit the address and click SAVE NOW or click the X icon to delete.
  5. If you no longer want the contact record, you can click the three vertical dots to the right of the pencil icon and select DELETE.
  6. Sign out of Gmail and log back in.

Delay Send or Undo Send

You can also buy some time for when you realize you may have hit “Send” in Outlook without carefully scrutinizing the recipients or you can “Undo Send” in Gmail. There are some options for your smartphones as well.

To Delay Send in MS Outlook:

  1. Click FILE.
  3. Click NEW RULE.
  5. Select conditions if you want to apply any. If you want it to apply to all messages you send, do not select any conditions. Hit NEXT. If you did not apply any conditions, hit YES when asked if you want it to apply to every message you send.
  6. Check the box next to DEFER DELIVERY BY A NUMBER OF MINUTES. Click on the underlined section of text when that command appears in the box below, and specify how many minutes you want it to be held before sending. Hit OK, and hit NEXT.
  7. Select any exceptions you want to apply. Hit NEXT.
  8. Name the rule, and select any rule options you want to apply. The TURN ON THIS RULE box should be checked, if nothing else.
  9. Hit FINISH.

Set Up Undo Send in Gmail:

  1. Click the gear icon towards the upper right corner of your screen and select SETTINGS.
  2. Select GENERAL (you’re probably automatically there).
  3. Scroll until you see “Undo Send: Send cancellation period…” Use the drop-down box to set it to 30 seconds, the maximum amount of time.

To USE undo send in Gmail:

  1. Send an email.
  2. A window appears in the bottom left corner of your screen. It says “Message has been sent,” and gives two options – UNDO and VIEW MESSAGE. To undo the send, hit UNDO.

It is also very easy to inadvertently email the wrong person from your smartphone email app. The options are less robust but there are some ways to reduce the risk.

Add a Delay to Outgoing Email in Android Email App:

  1. Open Email app
  2. Click on the vertical ellipsis
  3. Choose “settings”
  4. Click “Delay Email Sending”
  5. Check the box to delay email sending
  6. Click Set Length of Delay
  7. Choose between 3 and 30 seconds
  8. Close

Now when you click to send an email a countdown timer will appear over the email. You can click cancel if you realize you are sending an email you didn’t check carefully.

Add a Delay to Outgoing Email in iPhone Gmail App

  1. Once undo send is activated, it pops up on your mobile device in a similar fashion. Once you hit SEND, a black bar appears along the bottom of your screen. Just tap “UNDO” to recall the message. This option will be available for however long you select, up to 30 seconds.

Microsoft Outlook Add-ins

There are a number of third party tools for Microsoft Outlook that can help avoid sending an email to the wrong recipient.


From the website: “ReplyToSome is designed to prevent mistakes and absent-minded slips through three sets of features. The first is a user interface that displays email addresses in easy-to-read rows and allows users to quickly understand the “state of play” with respect to a given email. The second is a set of tools designed to help users automatically identify omitted or unintentionally added email addresses. These include our “Intruder Alert” tool which highlights any “outsider” address in what is supposed to be an internal message and our “Blackline” tool which allows users to compare the list of addresses in an email with previously used lists or distribution groups. The third set of features allows users to more easily create, modify, and use distribution lists, which can help simplify the process of gather addresses for multi-party communication.” The cost is $50 for the add-on is a one-time fee for a single user. Over 10 licenses can be negotiated.

Payne Group Outlook Send Assistant

From the website: “Outlook Send Assistant provides the extra layer of security needed before the send or reply all button is clicked and confidential or embarrassing information is released. It handles distribution lists, blind carbon copy notification handling, internal and external mail handling, and more. It is your “second chance” layer of defense against accidental disclosure. The administrator module called feature manager is available for enterprise clients that maintain annual maintenance. This tool allows you to configure many additional options to deploy to your organization.” The cost is $45 (once) per license. Over 20 licenses call for the enterprise version.

SendAware by TechHit

The Pro version prompts to confirm all recipients before you hit send. It also cautions you when there are multiple domains being responded to (internal and external), when there are new recipients in a message thread, and it can prompt you to encrypt messages based on certain criteria. It is completely configurable. The cost is $60 a year, and there is an enterprise version.

Keep Internal Communications Internal

Some of the more egregious missent emails are meant for internal recipients but sent externally instead. One way to reduce this factor is to consider using an alternative internal communication method, whether Slack, Microsoft Teams or a chat tool built into your practice management application like Rocket Matter’s Communicator. These tools will let you converse with your team but reduce the opportunity to inadvertently respond to an email where a client is cc’ed, or send an email to an outside party that was meant for an internal recipient. Plus, your inbox will be cleaner and it will be easier to manage client emails!


Inadvertently sending an email to the wrong person can be embarrassing or much worse. There is no magic solution to keep you from ever making another email mistake. Your best bet is to train yourself to pause, check the recipients, check for correct reply levels before hitting “send.” Consider not adding your recipient’s email address until AFTER you’ve done all this. It reduces the likelihood of you forgetting to run through the self-check, or of accidentally pressing send before you’re ready. Want to see some of these tools and techniques demonstrated? Watch the video “How To Prevent the “Whoops” Moment When Sending Email”.