Why You Should Delay Emails in Outlook

This post shows how to delay emails in Outlook using Schedule Send or Delay Delivery, including how to edit, cancel, or apply a default delay to every message. It also covers safer alternatives like Undo Send/Recall and points to practical security guardrails (email protection, DLP, encryption) if you want fewer risky mistakes.

When you delay emails with schedule send or delay delivery, you save yourself quick mistakes

We’ve all been there: you hit Send and immediately spot a typo… the wrong recipient… or the attachment you meant to include. That’s exactly why so many people choose to delay emails—sometimes it’s just awkward, and other times it can become a real business risk, especially if sensitive information lands in the wrong inbox.

The good news: Outlook gives you a few different “safety nets,” depending on which version you’re using—Schedule Send, Delay Delivery, and even a short Undo Send window.

If your company runs on Microsoft 365, we can also help you lock down email beyond simple delays—using controls like email protection and data-loss prevention so mistakes don’t turn into incidents.

How to Delay Emails in Outlook: Schedule Send vs. Delay Delivery

Outlook uses two different approaches:

  • Schedule Send (Outlook on the web / New Outlook / some Mac versions): You pick a future time, and Outlook keeps the email until that time. In Outlook on the web, the message stays in your Drafts folder until it sends.

  • Delay Delivery (Classic Outlook for Windows): Outlook places the message in your Outbox and sends it later. Microsoft notes Outlook needs to be online/connected for this to work, and some account types (like POP/IMAP) don’t support it.

Option 1: Schedule Send (Outlook on the web)

This is the simplest “send later” experience for most users.

  1. Start a new message in Outlook on the web.

  2. Next to Send, select the dropdown.

  3. Choose Schedule send.

  4. Pick a default time or set a custom time.

  5. Click Send.

After you schedule it, Outlook keeps the message in Drafts until the delivery time.

Pro tip: If you want to update or cancel it, go to Drafts, open the message, adjust, and reschedule.

Option 2: Schedule Send (Outlook for Mac)

If you’re on Outlook for Mac, Microsoft provides a dedicated “Schedule send” flow.
(Availability can depend on your version and mailbox type.)

Option 3: Delay Delivery (Classic Outlook for Windows)

This is the workflow your current post is describing—and it’s still very useful, especially in managed corporate environments.

  1. Compose your email.

  2. In the message window, go to Options (or Message) and open Delay Delivery / Delivery Options (location varies slightly by build).

  3. Check Do not deliver before.

  4. Choose your delivery date/time.

  5. Click Close, then Send.

Your message will sit in Outbox until the scheduled time.

Important: Microsoft notes this feature is not available for some mailbox types (like POP/IMAP), and Outlook must be online/connected for it to work as expected.

How to send it sooner (or cancel the delay)

  1. Open Outbox.

  2. Double-click the delayed email.

  3. Go back to Delay Delivery / Delivery Options.

  4. Uncheck Do not deliver before.

  5. Send normally.

Option 4: Add a delay to every email you send (Classic Outlook for Windows)

If you want a built-in “cooling off period” for every email, you can create a rule that defers delivery by a number of minutes (commonly used for 1–10 minutes).

This is typically done in Classic Outlook for Windows using Rules & Alerts (and is often limited to 120 minutes in the rule setting UI—i.e., up to 2 hours).

Best practice: Add exceptions so urgent emails or messages to specific internal addresses don’t get delayed.

Bonus safety net: Recall and Undo Send (when delay isn’t enough)

If an email already went out, you may have two other tools—depending on your environment:

  • Message Recall: Works in specific Microsoft 365/Exchange scenarios (and isn’t guaranteed). Microsoft’s recall guidance is here.

  • Undo Send (Mac): On Outlook for Mac, you can configure a short send delay (seconds) and hit Undo right after sending.

If email mistakes create real risk, add guardrails (not just delays)

Delaying an email is a great habit. But if you’re trying to prevent data exposure, wire fraud, or business email compromise, delays alone won’t solve the bigger problem.

A few practical guardrails that help:

  • Email protection + anti-phishing controls to reduce spoofing and malicious links. (MSG approach: layered email protection + filtering.) See our overview of security services on IT Security.

  • Data Loss Prevention (DLP): Policies that detect sensitive data and prevent accidental sharing. Microsoft’s overview of Purview DLP is a strong starting point.

  • Email encryption: If you truly need to send sensitive data, encryption policies can reduce exposure. Microsoft’s encryption overview is here.

If you want help tightening this up inside Microsoft 365, our team can configure and manage it as part of a clean, secure environment: Microsoft 365 Business Solutions. 
And if you want a broader “protect the inbox” approach (filtering, email protection, DLP concepts), our stack overview is here: Cloud IT Optimization.

Need help?

If Outlook features are missing, inconsistent across devices, or your mail flow needs to be locked down (so sensitive data doesn’t leave the building by accident), we can help you get Microsoft 365 working the way you do—simple, secure, and scalable. Contact us today.