Unsend Emails even after clicking “Send” in MS Outlook

By: Standss Contributor , Oct 31st, 2023

Have you ever sent an email and then regretted it? Or have you ever spotted a mistake in an email after sending it?

In such cases, recalling an email can be a useful feature, but it’s important to be aware of its limitations and potential downside.

There are two main ways to provide a safety net that allows recalls. You can use Outlook’s recall feature (which unfortunately does not work in most cases) or you can delay the email in your Outbox for a small time giving you a window to change your mind (for most people the need for recall usually becomes obvious almost immediately after clicking Send).

In this post, I will share the limitations of recalling an email using what is built into Outlook, and a powerful alternative which involves delaying delivery for a small time.

Download SendGuard for Outlook and Prevent yourself from sending inappropriate Emails.

How Recall works in Outlook?

Firstly, here’s a step-by-step instruction on how recall works in Outlook:

  1. Open your Sent Items folder.
  2. Double-click on the email message that you want to recall.
  3. From the message window that opens, select File > Info.
  4. Click the option to the right marked Resend or Recall, then select Recall this Message.
  5. Select Delete unread copies of this message to recall the sent message.
  6. Select Delete unread copies and replace with a new message to replace the sent message with a new message.

Why Email Recall is not reliable?

Email recall is not always effective. It depends on the recipient’s email system and settings. If the recipient has already opened and read the email, the recall will likely be ineffective.

Email recall is time sensitive. If you realize your mistake too late, the recipient may have already read the email and acted upon it. It’s more effective if you catch the error shortly after sending.

In Outlook, for recall to work you must have an Exchange account and the recipient must be in the same Exchange organization. If you are using a POP3, IMAP, or Outlook.com account, or if the recipient works for another company, you cannot use Recall.

Another factor to consider is that Recall only works if the recipient is using Outlook to read their emails. If the message is being read via Outlook on the Web (OWA) or on a smartphone or tablet, the recall will not work.

When you attempt to recall an email, it can sometimes draw more attention to the email. The recipient may receive a notification that you are trying to recall the message, which could lead to them specifically checking the content of the email.

Why Delaying Emails is more Reliable?

In such cases, delaying emails can serve as a safety net. It gives you a brief window to retract the message or make necessary corrections before it reaches the recipient’s inbox.

However, delaying emails in Microsoft Outlook is challenging and cannot be easily implemented at an organizational level.

We will show you how you can delay emails in Outlook using an addin called SendGuard for Outlook.

Use SendGuard to Delay Emails

SendGuard for Outlook is a SaaS based application that allows you to easily delay emails. You can also configure the application to delay emails sent to specific email addresses or domains.  

Once you have installed the SendGuard add-in in Microsoft Outlook you need to set-up the Delay Guard component of it to delay sending your emails.

This is a simple process and you only need to specify the number of minutes you want to delay your emails by and the email addresses/domains you want to delay them for.

For urgent emails you can bypass the delay delivery rule, by selecting the Send Now option.

You may have noticed that SendGuard has other security features apart from Delay Guard.

SendGuard is an email security add-in for Outlook that prevents accidental data disclosure by prompting users to confirm recipients and attachments in outgoing emails (see screenshot above).

This performed by the SendConfirm module of SendGuard.

If you are an existing customer who has SendGuard Standard (SendConfirm) license, you get Delay Guard at no extra cost.

To learn more about SendConfirm read this post- Prompt users when emailing external recipients in MS Outlook.

Contact Us

Email Mistakes don’t have to become security incidents. Talk to an expert on sales@standss.com to learn about implementing SendGuard.

SendGuard for Outlook


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Photo by RDNE Stock project from Pexels

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