How to Unsend an Email (and Avoid Email Mistakes in the First Place)

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unsend an email

You hit send on an email, and immediately wish you could take it back.

Maybe you realize too late that you emailed an important document to the wrong person, or accidentally CCd someone on a conversation that they definitely shouldn’t have been a part of. Or, maybe you took a snappy tone with a rude customer out of anger, and now you regret it.

Can you come back from an email mistake and unsend an email?

The short answer? Sometimes. The longer answer? There are several things you can do before sending an email that can lessen the likelihood of email missteps in the first place. And, yes, there are some instances when you can actually take back an email mistake.

Here’s what to do in case of email mistakes while writing an email, before you press send, and after you’ve sent an email.

While you’re writing an email

It would be better if you could simply avoid making mistakes altogether, right?

Here are two things you can do before you sit down and while you’re writing, so you don’t have to worry about unsending an email (or apologizing for it later).

Slow down and collect yourself

Before you even start writing, take a deep breath.

Even though email is somewhat impersonal, it can still bring up strong emotions. If you are responding to an irate customer, for example, you might feel your blood boiling as you type a curt response. On a similar note, if you are responding to a colleague who just can’t seem to understand what you are saying, your frustration is bound to spill over into your email response.

So, take some time to settle and compose yourself. It’s a step that sounds easy, but will help prevent common email mistakes from happening in the first place.

Consider the appropriate voice and tone

Do you have an email voice and tone guide for your business? If not, it’s definitely a good idea to create one.

If you don’t have one yet, take a second to think about the appropriate voice and tone for your business, and how that plays into this particular email response. Is your company voice friendly and a little playful, or is it buttoned up and serious? Your email, no matter the emotion you are currently feeling, should still reflect the voice and tone you’ve established for your business.

To refer back to the example of responding to an angry customer, if your business typically takes a friendly, conversational tone, a direct, angry email is going to go against your brand image, and potentially sour a relationship with a customer. 

If you don’t consider your voice and tone, you might find yourself wishing you could unsend an email because you’ve realized too late that it doesn’t “sound” like your business.

Before you hit send

So, you’ve written your email.

But, there are still several steps you should take before you hit the send button.

Re-read emails before you send them

Read your email. Now, read it again. Wait 10 minutes. Read it a third time. Read it backward. (Okay, that last one was a joke.)

Just because you’ve read an email doesn’t mean you’ve caught every mistake. It’s hard to catch our own errors because we read by intuiting meaning—and we obviously know what we mean, so mistakes go unnoticed more easily.

Beyond re-reading word by word over and over again, a good workaround is a voice to text tool; hearing your words read aloud will help you notice mistakes easier. Plus, you might pick up on something you missed by reading—like an unprofessional tone, or poor word choice.

Have someone look at your draft

Another way to catch errors you might have missed is to have someone else give your email a once-over before you send it off. Using an email tool like Outpost where you can write notes and share drafts to another member of your team can help here.  

Ask them to be as candid as possible. Having someone else read over your email can help with more than just catching errors; someone with a little more distance will likely be able to call out inappropriate voice, accidental information-sharing that should have been kept private, or other similar email mistakes.

Use a spelling and grammar tool

I’m a huge fan of Grammarly; I have the Chrome app installed in my browser, and I use the desktop version too for longer pieces of writing.

Having a tool to quickly check your spelling and grammar is a valuable failsafe. It will never substitute having a real, live person look over your email (just one editor’s opinion), but it works well in conjunction.

Take advantage of features and add-ons that will help you spot mistakes

Did you know that Gmail has a feature that will point out if you’ve forgotten to attach a document? It will automatically give you a prompt if you’ve mentioned that something is attached and you haven’t included an attachment, so keep an eye out for it.

On that note, if you are a Gmail user, there are plenty of Gmail add-ons that will help you customize your email experience and make you more productive.

After you’ve sent the email

So, you clicked send, but you know there’s a mistake in it, or maybe it was sent to the wrong email address. What should you do?

Unsend an email by enabling a tool

Sometimes, even after all the checks and precautions, you just really want to unsend an email.

The good news is that you can actually do that—in certain contexts, during a very brief window of time, directly after sending the email, and only if you already have a tool installed. (See why it’s better to avoid email errors in the first place?)

Gmail has an “undo send” feature that can be enabled by going to your settings (here’s a more in-depth description of how to find this feature). You have the option to set the cancellation period duration for 5, 10, 20, or 30 seconds. So, not a very long window—but a great option if you realize immediately that you emailed the wrong person, or forgot to include an important detail.

If you think there’s a chance that you’ll use this feature, turn it on right away—you can’t turn it on after the fact and be able to unsend an email that you’ve already sent.

Not every email provider offers this feature, however. Office 365, for example, does have a “recall” feature, but it has some huge limitations—namely, that it only works between two Office 365 or Microsoft Exchange email accounts within the same organization.

Also worth a quick mention here is the tool Digify, which allows you to unsend attachments. So, if you sent a confidential attachment to the wrong person, you can revoke access and they won’t be able to open it. If you send a lot of attachments with sensitive information and are worried about them falling into the wrong hands, it might be worth your while. However, it’s not unsending an email, so it’s not quite universally applicable.

Make the first move—quickly

So, you sent an email that you wish you could unsend, but you can’t. Maybe you didn’t have the Gmail’s undo tool enabled yet, or maybe you realized too late that you’d made a mistake.

First, take a breath. It might be embarrassing, it might be bad news, but it probably won’t be earth-shattering.

The next thing you should do is immediately reach out to whomever received the email with the mistake and own up to it.

This will look different depending on the context; an interdepartmental email that was accidentally sent to someone outside your organization will require different follow-up tactics than a customer who got the wrong information.

Whatever the situation, the takeaway here is: move fast and take responsibility.

Apologize, and see if there’s anything you can do to make it right

On that note, your follow up email should include an apology.

Again, the right type of response will vary depending on who the email went out to. If a customer got the wrong information, email them with an apology, the correct info, and maybe a special discount code if you feel it’s appropriate. If you accidentally CCd a colleague on an email that was rude, unprofessional, or accidentally shared sensitive information, you’ll have to handle the situation a little differently.

We’ve talked about how to write an email apology on the Outpost blog, and shared an email apology template, which is a good place to start. I’d recommend checking out my article on whether or not the customer is always right, too—because sometimes it can be hard to check your own emotions when dealing with an upset customer, and you might find yourself apologizing for your tone.

unsend an email

Think before you send

The takeaway here:

Frantically searching for a tech solution that will help you unsend an email is a bit beside the point.

It’s important to think through your emails, take your time, and consider how you are representing your business before you send an email, rather than trying to do damage control after the fact.

Mistakes happen. You’re bound to accidentally send an email with a typo every once in a while. But, by slowing down, taking precautionary steps before you hit send, and making sure that you don’t let an emotional response dictate your email response, you can lessen the likelihood that you’ll need to unsend an email at all.

Posted in Email

Briana Morgaine

Briana Morgaine

Briana is the content marketing specialist for Outpost and Palo Alto Software. She enjoys discussing marketing, social media, and the pros and cons of the Oxford comma. Briana is a resident of Portland, Oregon, and can be found working remotely from a variety of local coffee shops.