How to Recall an Email in Outlook: A Mac Expert‘s Guide (2023)

We‘ve all been there. That sinking feeling when you realize you just sent an email you shouldn‘t have. Maybe it had a glaring typo, accidentally cc‘d the wrong person, or worse, included something that could get you fired.

If you‘re an Outlook user, you might be frantically Googling how to recall an email. While Outlook does have a recall feature, it‘s not foolproof. As a Mac software expert, I‘ll walk you through exactly how to unsend an Outlook email, the technical requirements and limitations, and what to do if a recall fails. Plus, I‘ll share some pro tips to avoid embarrassing email mistake in the first place.

The Psychology of Regrettable Emails

First off, know that you‘re not alone in regretting a sent email. A 2019 study by Klaviyo found that 58% of people have sent an email they immediately wished they could take back. The most common reasons? Clicking send too soon, anger or frustration, and drinking (yep, drunk emailing is real).

There‘s actually a psychological basis for firing off emails we later regret. When we‘re stressed, anxious, or facing a time crunch, the amygdala (the "fight or flight" part of the brain) can override the prefrontal cortex (the "think it through" part). Impulsivity takes the wheel and we hit send without considering the consequences.

While this stress response had evolutionary advantages back when we were cavemen facing literal tigers, it‘s not so helpful in the modern workplace. Hence the need for an unsend button.

How to Recall an Email in Outlook Step by Step

So you‘ve realized you sent an email you shouldn‘t have. Here‘s how to attempt to recall it in Outlook on Mac:

1. Act fast. You have the best chance of recalling an email if you do it before the recipient reads it.
2. Open the Sent Items folder.
3. Double-click the message you want to recall to fully open it.
4. In the top menu, select Message > Actions > Recall This Message.
5. Choose whether to Delete unread copies of this message or Delete unread copies and replace with a new message, then click OK.
6. If you‘re replacing the message, make your changes and hit Send.
7. Cross your fingers and wait for the outcome.

Here‘s what the recall message window looks like:

Requirements for Recalling an Outlook Email

For your unsend attempt to work, certain technical requirements must be met:

1. Both you and the recipient must have Microsoft Exchange Server accounts within the same organization. Recalls aren‘t possible with external email addresses or non-Exchange accounts.
2. You both need to be using the Outlook desktop app. Recalls don‘t work with Outlook on the web or mobile app.
3. The original message must be unread in the recipient‘s inbox. If they‘ve already opened it or moved it to another folder, the recall will fail.

It‘s also important to note that even successful recalls may still generate a notification for the recipient letting them know you unsent something (though the contents of the original email will be deleted).

What Happens if an Outlook Email Recall Fails

There are a number of reasons an unsend attempt can fail:

• The recipient opened the email before you tried to recall it
• The recipient‘s inbox has rules that moved the email out of the inbox
• The original email was touched by a third-party add-in or filtering system
• The recipient is using a non-Outlook email client or older version of Outlook

In fact, a 2017 analysis by Egress Software found that around 76% of email recall attempts are unsuccessful. Not great odds.

What‘s worse, a failed unsend can actually draw attention to your email flub by generating an odd notification for the recipient. Instead of quietly disappearing, your mistake email gets an added layer of intrigue.

Outlook Alternatives for Mac with Undo Send

If you don‘t want to rely on Outlook‘s finicky recall feature, several other email clients popular with Mac users offer more forgiving undo send options:

• Gmail: Undo send is turned on by default, with a 5 second delay to cancel a sent message. You can increase the cancellation period to 10, 20, or 30 seconds.
• Apple Mail: No native undo send feature, but you can use a plug-in like Mail Butler or Mailbutler to defer sending by up to 30 seconds.
• Spark: Allows you to undo a sent email within 5 seconds.
• Polymail: Paid email client with undo send up to 10 seconds.

Here‘s a comparison chart of undo send options across popular email clients for Mac:

Client	Undo send delay options	Enabled by default?
Gmail	5, 10, 20, 30 seconds	Yes
Apple Mail	None (requires plug-in)	No
Outlook	None	No
Spark	5 seconds	Yes
Polymail	10 seconds	Yes

Email Recall Alternatives: The Art of Damage Control

So what if your attempts to unsend an email fail or you‘re not using an email client with an undo button? Time for some professional damage control:

• Own up to the mistake. Send a follow-up email acknowledging the error. Briefly apologize and clarify if needed. A little humility can prevent hurt feelings or misunderstandings.
• Don‘t draw more attention to it. If it was a minor flub, sometimes it‘s best to just let it go rather than sending repeated recall attempts or long-winded apologies.
• Talk it out in person. If your email contained harsh words or sensitive info, an in-person conversation (or call) can go a long way in smoothing things over. Emails are easily forwarded, and you may deeply regret putting something in writing.
• Learn and move on. Beating yourself up over an email mistake won‘t unsend it. Treat it as a teachable moment and identify what you can do differently next time (like implementing the tips below).

Tips to Avoid Needing the Unsend Button

As a Mac software expert who has seen all manner of digital communication mishaps, here‘s my advice for avoiding that cringe-inducing "oh no" moment after hitting send:

1. Take a pause. Our inboxes move at a breakneck pace, but that doesn‘t mean you have to match it. If you‘re feeling heated or rushed, step away from the email for a bit. That snarky reply or over-sharing details can wait.
2. Proofread every email. Typos and tone problems are especially easy to overlook when we‘re in a hurry. Read important emails out loud or paste them into a text-to-speech reader before sending.
3. Double-check the recipient. Pay close attention to the auto-fill on email addresses and ensure you‘ve got the right person. Also watch out for accidental "reply all" clicks.
4. Configure delay send. If you‘re using Outlook, you can set up a rule to delay outgoing messages by a few minutes. This gives you a grace period to undo or edit emails before they reach the recipient.
5. Keep it professional. The work inbox isn‘t the place for emotional venting, sensitive info, or off-color jokes. Save that for Slack or Signal chats with trusted colleagues.
6. Know your company‘s email policies. Some organizations have strict rules and monitoring around email usage, and even an unsent email could be grounds for disciplinary action. When in doubt, err on the side of caution.
7. When in doubt, save it as a draft. If you‘re not sure if an email is a good idea, save it as a draft first. You can always revisit and revise later (or realize you‘re better off not sending at all).

Conclusion

Outlook‘s recall email feature can be a lifesaver when you‘ve made a cringe-inducing email faux pas. But it‘s not guaranteed, and attempting an unsend can sometimes make the situation worse.

As a Mac software expert, my advice is to prevent regrettable email scenarios from the start with mindful email habits. Pause before hitting send, proofread everything, and keep things professional. And if you do make a mistake, own up to it and focus on damage control rather than trying to erase all evidence.

At the end of the day, we‘re all human and email mistakes happen. The important thing is to learn from them, communicate with empathy, and keep pursuing inbox zero.