Undo Send: Use cases from experts

Despite all the instant messaging apps on the market, email is the go-to tool for formal communication.

It’s through email that we apply for jobs, send sales pitches, negotiate and close deals, collaborate with colleagues and business partners remotely, and even reach out to elected officials.

It goes without saying that this type of communication calls for professional language, a defined structure, and clarity - even the smallest of mistakes can be costly.

That’s precisely why you should always proofread your emails before you hit the “send” button.

But what if you see you’ve misspelled your recipient’s name or attached the wrong file after you send the message?

Well, the only thing that can save you the embarrassment of sending a second email apologizing and explaining what happened is an “undo send” feature.

If your free email provider doesn’t offer such an option, you can install a third-party “unsend email” tool.

Since Gmail, Apple Mail, and Outlook are the three most popular email clients at the moment, this blog post will focus on them and explain how their users can recall email messages when needed.

How to unsend an email in Gmail

You can recall an email in Gmail using the native “Undo Send” feature. You can cancel a Gmail message shortly after you send it by selecting the “Undo” option that will appear in the bottom left corner of your computer screen.

If you use your smartphone to send emails, you can retract a message by tapping “Undo” right after you send it.

Gmail allows its users to choose one of four predetermined send cancellation periods: 5, 10, 20, or 30 seconds. Here’s how:

• Step 1: Go to Gmail on your computer (you can’t make this change on a mobile device).
• Step 2: In the top right corner, click on the Settings button (the little cog icon) and select “See all settings.”
• Step 3: Find the “Undo Send” row (right below “Maximum page size”) and pick one of the four send cancellation period options.
• Step 4: Finally, go to the bottom of the page and click on “Save Changes.”

How to unsend an email in Apple Mail

Apple Mail users can recall messages with the native “Undo Send” functionality.

If you want to pull back a sent email in the Apple Mail app on your iPhone or iPad, you need to follow these three simple steps:

• Step 1: Tap the “Undo Send” option at the bottom of your inbox right after you hit the “send” button. Keep in mind that you only have 10 seconds to change your mind and retract the message.
• Step 2: Once you’re taken back to the email compose window, review and edit the original email. Here, you don’t have to hurry as the message is already unsent.
• Step 3: When you’re done correcting mistakes, tap the blue arrow at the top of your screen to send the message.

Mac users can unsend incomplete, incorrect, or otherwise problematic email messages starting with the “Undo Send” feature. It, too, is available for 10 seconds after sending. Here’s how to use it:

• Step 1: Make sure the Apple Mail sidebar is showing. If the sidebar (the left column that displays all of your mailboxes) isn’t showing, click on “View” and then select “Show Sidebar” to make it appear.
• Step 2: Once you send an email, look for the “Undo Send” option at the bottom of the sidebar and click on it before the 10-second time window elapses.
• Step 3: Review and edit the message before you send it again or simply delete it.

Undo Send makes the whole email unsending process extremely easy.

Whenever you send an email, a small box containing the key details of the message and a 10-second timer pops up.

If you notice you’ve attached the wrong document or misspelled a word in the subject line, you can hit “Undo Send” and pull back the email right away.

Once you do, you’ll be able to make the necessary improvements and resend the message, thus avoiding leaving a bad impression.

How to unsend an email in Outlook

To recall an email in Outlook.com, you first need to turn on the “Undo Send” option. Here’s how:

• Step 1: Click on the Settings icon at the top of the page and select “View all Outlook settings.”
• Step 2: Click on “Mail” and then select “Compose and reply.”
• Step 3: In the “Undo Send” section, choose how long you want Outlook.com to wait to send your emails. You can delay sending your messages for 5 or 10 seconds.
• Step 4: Save your choice.

Once you set this up, you’ll be able to cancel messages before they reach your recipients’ inboxes by clicking on the “Undo” prompt at the bottom of your message list.

This option will be available to you for 5 or 10 seconds, depending on the choice you made when you activated the “Undo Send” feature.

Now let's hear some use cases and funny stories from professionals worldwide.

Sending the wrong email 

While I would like to be able to say that I never make mistakes and send emails to the wrong people without realizing it, that would be a lie.

Everyone makes mistakes, but luckily, we now get the option to fix those mistakes before the wrong recipient receives an email meant for someone else.

I have a business associate whose email begins with the same three letters as my wife's email. I have to admit to regularly sending and promptly unsending all manner of emails to him.

I once tried to send him additions to the grocery list three times before I got it right.

It got bad enough that my wife eventually created a new email account just to save me from myself

James Green, Owner, Cardboard Cutouts

The typo save 

Everyone is aware of autocorrect's annoying tendency to introduce embarrassing words into conversations.

The best and funniest have their own websites. Uncomfortable autocorrects have grown to be a constant menace as more of us write emails from mobile or tablet devices.

Additionally, hasty typing on a desktop or laptop computer might lead to full-blown humiliation.

The worst beneficiaries? Bosses and parents.

But remember - it's very uncommon for employees to face disciplinary action at work for breaking email protocol, and while a typo is usually not grounds for termination, it may still be quite embarrassing. 

Steve Pogson, Founder & E-commerce Strategy Lead, First Pier

Mistaken invoice 

I received my invoice from a friend who runs a healthcare business.  

She regularly runs blood tests and other medical tests on me, and sends an invoice at the end of the month with her fees.  

Well, her invoice came in, as usual, I glanced through it and stored it away for later. 

It was my turn to send my invoice to one of my clients, and guess what I attached?  

The invoice with details about the tests I had had run in the past month!  

I realized my mistake as I watched the "undo email" slowly countdown, and I have never moved that fast.  

I managed to unsend. I uploaded the right invoice (after double-checking twice!), and I sent a quick prayer of thanks to the developers that included the unsend email feature!  

Claire Grayson, Co-founder, Personality Max

The cat sent the email

Recently I was writing our quarterly report email that I send out to our leadership teams.

It's a fairly important email, and I tend to proofread it quite a few times before I send it out because it needs to be clear and provide the correct information. 

While I was writing it, my cat hopped up onto my keyboard and pressed a bunch of buttons-- one of which included the "send" button.

I watched my email tell me that my message was sending and had the clarity of mind to hit that "undo" button before it was sent off.

Luckily I'd caught it. Most of what was in there was gibberish from the cat!

Larry Snider, VP of Operations, Casago Vacation Rentals

Discovering the undo send option 

It's a short and quite funny story about how I discovered the undo send option.

Due to my profession, I exchange emails with collaborating managers and journalists on a daily basis. 

Usually, I have many conversations going on at once, so it's easy to confuse them.

No wonder I mixed up my contacts and sent an email to the wrong person one day. 

However, I felt highly embarrassed because it was the first email I had sent her, and my mistake ruined the first impression. 

As soon as I figured out what I had done, I sent the apologies, starting with the line - I wish my email had an undo send option. 

"Actually, you have this option," she replied politely, and she sent me an article explaining how to find this setting in my mailbox.

Surprisingly, my error began a fruitful collaboration and long-term business relationship.

I would lie if I said I never made the same mistake again, but luckily, I learned how to correct it quickly.

Leszek Dudkiewicz, Head of Marketing, Passport Photo Online

Make mistakes in URLs

As a link-builder, most of my email messages include a link and sometimes multiple links. When writing my messages, I might forget something or type very quickly and make mistakes in the URLs. This is when the Undo button comes to help. 

When I send the email and notice I wrote the URL incorrectly, the button helps me get my email back and make the changes.

For example, if it’s a link to a social media scheduling tool, I may mistakenly add a comma or other punctuation marks.

But the Undo button has saved me from a lot of unpleasant situations, and I’m sure it has saved other link-builders as well.

Ani Apitsarian, SEO Specialist, SayNine

Last second subject line change

The subject line is arguably the most important part of your email. Especially if it’s a cold email, the subject line will catch the reader's attention and be the reason they either open or ignore your email.

I’ve sent cold emails, where in the last second, I’ll realize I can come up with a more engaging subject line. In those cases, I’ll use the undo button to rethink what is the most effective subject line, and then press send.

Darshan Somashekar, Founder, Unscrambled Words

Summary

Formal email communication calls for professional language and clear formatting.

Formal emails should practically be flawless, but even the most detail-oriented person can make mistakes, especially when in a hurry. This is exactly why the “undo send” email option is a lifesaver.

Unfortunately, not all email service providers offer an “undo send” feature.

However, there are plenty of reliable third-party email apps that provide users with a robust set of features, including an unsend one.