How do I delay delivery of emails in Outlook?

Scenario: You scheduled an email to send using the Outlook client on your work computer, but it didn't go out until you turned on your computer and signed back in. 😱

Solution: It's best to use Webmail to schedule delayed emails. 👈👈😎 (Alternatively, you can use Outlook within the Remote Desktop environment.)

How to delay or schedule sending email messages

Webmail method

1. Navigate to your organization's Remote apps page and click Webmail.
2. Compose your message. Then, instead of clicking the Send button, click the arrow to the right of the Send button. You will see a dropdown menu. Select Send later.
   
3. A new window will pop up where you can select the date and time, then click Send.
   

You'll find your scheduled email in the Drafts folder of your Webmail window. You can sign out of Webmail and your email will still send according to schedule.

Remote Desktop method

1. Navigate to your organization's Remote apps page and click Remote Desktop.
2. Open Outlook within the Remote Desktop window.
3. Compose your message. When you're done, navigate to the Options tab, then click Delay Delivery. (If you don't see the Options tab and you are replying to an email, you may need to click the Pop Out button at the top right of the reply window.)
   
4. Check the box for Do not deliver before, then set the date and time and any other desired settings. Once you're ready, click Close.
5. You should see the Delay Delivery button is selected. Now you can click the Send button to schedule your email. 
   

You'll find your scheduled message in the Outbox folder within Outlook within Remote Desktop. You can sign out of Remote Desktop and your email will still send according to schedule.

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Technical context

Outlook can run in two different modes: Online or Cached.

Cached

Cached mode is the default mode for the Outlook client on your work laptop, and it's the preferable mode for day-to-day work. What this means is that it downloads a "cache" (like a copy) of your email data and stores it locally on your computer. So even if your internet goes down, the cached data is there for you to reference, allowing you to continue working offline.

The downside of cached mode is that in order to send your scheduled email at the desired time, Outlook must be running at the time it is scheduled to be sent out.

Online

Online mode means that Outlook reads all data off of the server in real time. As your internet connectivity fluctuates, or if you click on a large attachment, Outlook may freeze or lag until the data is pulled. If your internet goes down, you may not be able to retrieve existing emails for reference. 

Online mode works best for machines that stay put on the local network right next to the Exchange server. This is one of the reasons it is used in a Remote Desktop configuration, where the Remote Desktop server sits on the same local network as the Exchange server at all times.

The plus side of online mode is that it allows you to send a message set for a future time. The message actually goes to the server, which queues it and takes care of the future delivery regardless of what your Outlook client is or isn’t doing at the time.