Delayed delivery in Outlook breaks when the message is scheduled in the wrong Outlook version, held offline, or blocked by a rule or add-in. The fix depends on whether you use new Outlook, Outlook on the web, classic Outlook for Windows, or Outlook for Mac. Start with the current scheduling option for your version, then move through the Outbox, rules, add-ins, and repair steps that stop messages from leaving.
Use Schedule send in new Outlook
The most common cause is using classic Outlook's Do not deliver before steps in new Outlook, where the current feature is Schedule send.
Start a new message, add your recipients, and write the email.
Select the dropdown next to Send, choose Schedule send, pick one of the suggested times, and select Send.
For a custom time, choose Schedule send, set the date and time, and select Send.
The scheduled message stays in Drafts until Outlook sends it. Schedule send works in new Outlook for Windows, Outlook.com, and Outlook on the web, but not with IMAP or POP accounts.
Schedule it from Outlook on the web
Use this method when delayed delivery fails in the desktop app or you want to schedule from the browser. Outlook.com and Outlook on the web use the same current Schedule send flow.
Open Outlook in your browser and compose the message.
Select the dropdown next to Send, choose Schedule send, pick a default option or set a custom date and time, then select Send.
To send it early, open Drafts, open the scheduled message, select the Edit pencil icon, and choose Send Now.
Check the Mac account requirement
Outlook for Mac uses Schedule send; previous versions called it Send Later. The feature is only available in a Microsoft 365 subscription, Outlook 2019 for Mac, and Outlook 2021 for Mac, and it requires an Exchange account such as Outlook.com hosted on Microsoft 365 or Exchange 2016 CU5 and later.
It does not work with IMAP or POP accounts such as Gmail, Yahoo, or iCloud. With those account types, Outlook for Mac does not provide delayed delivery for outgoing mail.
To schedule a supported account, compose the message, add recipients, select the dropdown arrow on Send, choose Schedule send, enter the date and time, and select OK.
To cancel it, open Drafts, open the email, select Cancel Send, and confirm with Yes.
Set classic Outlook delayed delivery
Classic Outlook for Windows still uses Do not deliver before, and the setting lives in message options.
- 1.Compose the email, then select the Message Options arrow in the Tags group.
- 2.If you use the simplified ribbon, open Options and select More commands.
- 3.Under Delivery options, select Do not deliver before and choose the date and time.
- 4.Select Close, then select Send.
- 5.Keep Outlook online and connected at the scheduled time.
Keep classic Outlook online
This fixes delayed messages that sit in Outbox because classic Outlook was offline, disconnected, or closed when the scheduled time arrived.
Check the Outlook status bar for Disconnected, Working Offline, or Trying to connect.
Open Send/Receive.
Select Work Offline in the Preferences group to switch Outlook back online.
Open the delayed message again and select Send.
If the message still waits, choose Send/Receive.
When classic Outlook uses Cached Exchange Mode, leave Outlook running and connected at the scheduled time. For the most reliable scheduled send, use Do not deliver before while Outlook is running in online mode.
Remove a delay rule
Open classic Outlook and go to Rules, then Manage Rules & Alerts.
Select the Email Rules tab.
Inspect each rule description for defer delivery by # minutes.
Double-click the rule that is delaying messages.
Clear defer delivery by a number of minutes.
Classic Outlook can delay sent messages by up to 120 minutes, and Outlook for Mac does not support systematic delay rules.
If Viva Insights offers a Schedule send suggestion, turn off Outlook rules that delay messages so the suggestion can work cleanly.
Send a stuck delayed message now
A scheduled classic Outlook message can stay in Outbox until you remove its delivery restriction. Open Outbox, open the delayed message, and select the Message Options arrow in the Tags group.
In the simplified ribbon, open Options and select More commands. Under Delivery options, clear Do not deliver before, select Close, and then select Send.
If the Send button is missing or the message will not resend, close the message, reopen it from Outbox, make any needed edit, and select Send again.
If this method fails, check whether an add-in or signature is delaying Outlook send.
Disable add-ins and signature images
Use this method when Outlook pauses, hangs, or sends slowly after a signature tool or another add-in was added. In new Outlook for Windows, signature add-ins and inline signature images can delay sending: Microsoft documented signature add-ins leaving messages stuck in the Outbox because inline images load slowly, and released a fix that finished rolling out in September 2025. Update new Outlook first, then use the steps below if the delay persists, because Microsoft still lists uninstalling the signature add-ins or removing the inline signature images as the workaround.
In new Outlook or Outlook on the web, go to More apps, select Add apps, then open Manage your apps.
Find the app, select More options, and choose Remove.
In classic Outlook for Windows, open File and select Manage Add-ins.
On the web add-in page, clear the checkbox in the Turned on column for the add-in.
To test classic Outlook without add-ins first, right-click Start, choose Run, type Outlook.exe /safe, and select OK. You can also press Windows key + R, type Outlook /safe, select OK, choose your profile, and select OK.
For Outlook for Mac, open your preferred browser and go to https://aka.ms/olksideload. In Add-Ins for Outlook, review installed or admin-managed add-ins and remove the add-in causing the send delay.
Update or repair Outlook
This fixes delayed delivery problems caused by an outdated app, damaged Outlook profile, or broken Office installation.
On Windows, open Word or another Microsoft 365 app and create a new document.
Go to File, Account, Product Information, Update Options, and Update Now.
If updates are disabled, choose Enable Updates first.
On a Mac, open Word or Excel, choose Help from the menu bar, and select Check for Updates.
When Microsoft AutoUpdate opens, select Update or Update All, then restart Outlook.
To repair a classic Outlook mail profile, open Outlook and go to File, Account Settings, Account Settings, then the Email tab.
Select the account, choose Repair, follow the wizard, and restart Outlook. Repair is not available if you use Outlook 2016 to connect to an Exchange account; on that setup, update Outlook and use the Office repair steps below instead.
To repair Office on Windows 11, right-click Start, open Installed apps, select your Microsoft 365 or Office product, choose the ellipses, select Modify, then choose Online Repair and Repair.
On Windows 10, right-click Start, open Apps and Features, select Microsoft 365 or Office, choose Modify, then run Online Repair.
Online Repair appears on Click-to-Run installations, the most common type. On an MSI-based installation, the Change your installation window opens instead: select Repair, then select Continue.
On work or school devices, ask your administrator to review centrally deployed Outlook add-ins if you cannot remove the add-in yourself.
Frequently Asked Questions
Why does my delayed Outlook email stay in Drafts?
In new Outlook, Outlook.com, Outlook on the web, and Outlook for Mac, scheduled messages stay in Drafts until the scheduled delivery time. That is normal behavior.
Why does classic Outlook delayed delivery stay in the Outbox?
Classic Outlook can hold delayed messages in the local Outbox, especially with Cached Exchange Mode. Outlook needs to be running, online, and connected at the scheduled time.
Does delayed delivery work with Gmail, Yahoo, or iCloud in Outlook for Mac?
No. Outlook for Mac Schedule send is not available for IMAP or POP accounts such as Gmail, Yahoo, or iCloud.
Can Outlook delay every sent message automatically?
Classic Outlook for Windows can use a rule to defer delivery by up to 120 minutes. Microsoft states systematic delay rules are not available in Outlook for Mac.