Delay Delivery is a great option when you prepare an email in advance of when you want it sent. If you haven’t used the feature before, here are the steps.

For Outlook — Windows desktop version:

1. In the message you are composing, click the Options tab.
2. In the More Options group, click Delay Delivery.
3. Under Delivery options, check the box for Do not deliver before and select a date and time. Click Close.
4. In the message window, click Send. Now, the message remains in the Outbox folder until the delivery time you selected.

For Outlook — web version:

1. Compose your message and then select the dropdown menu next to the Send button.
2. Select Send later.
3. Select the date and time you’d like the email to be delivered (the window will suggest common times, but you can click “Custom time” to enter your own) and click Send.

A common challenge when using Delay Delivery in the desktop version is that the email will only send when the Outlook application is open. This can defeat the purpose of delaying the send if the point was to send a message while you are out of the office, for example.

This is because the desktop version of Outlook is running in Cached Exchange Mode. When you enable the Do not deliver before option, the message is stored in the local Outbox, not on the server.

However, there are two workarounds for this problem.

You can opt to use the web version of Outlook whenever you want to delay a send. Those emails will be saved to the server and send at the time you selected.

Atlernately, you can change the settings of your Windows desktop version of Outlook so that it doesn’t use the default cached mode. Here’s how: 

1. Click File in the top left of the Outlook task bar.
2. Select Account Settings in the main window.
3. In the Email tab, click Change.
4. Uncheck the box next to Use Cached Exchange Mode.
5. Click Next. When the message Account successfully updated appears, click Done.
6. Exit, and then restart Outlook.

Note: Any messages already scheduled for delayed delivery in your desktop app and stored in Outlook’s local Outbox will be lost when you make this change. Save them as drafts, first, then schedule them for delay delivery after you’ve made the change and restarted Outlook.