Outlook Cannot Send This Item Error [Windows 11/10]

The Outlook cannot send this item error can appear in Outlook on Windows 11 and Windows 10 for several reasons. Your message might contain a large attachment, the Outlook app might have a temporary glitch, or an add-in could be interfering with the sending process. In some cases, a damaged Outlook profile, an oversized email, or a problem with your mailbox can also cause the issue.

In this guide, you’ll learn how to fix the “Outlook cannot send this item” error step by step.

Outlook Cannot Send This Item Error [Windows 11/10]

The “Outlook cannot send this item” error means Outlook is unable to send the selected email as expected. The problem may be related to the message itself, attachments, Outlook settings, add-ins, or your email account.

To fix the error, try sending a new test email, remove or reduce large attachments, restart Outlook, disable problematic add-ins, and check your account settings. If the problem continues, you can repair Office, create a new Outlook profile, or use Outlook on the web to determine whether the issue is limited to the desktop app.

Before trying the advanced fixes, save a copy of your email content somewhere safe. If the message is important, avoid deleting it from your Drafts or Outbox folders until you’ve confirmed that you no longer need it.

1: Restart Outlook and Try Sending a New Email

Sometimes Outlook runs into a temporary problem that prevents a particular message from being sent. Restarting the app is one of the easiest ways to check whether the issue is temporary.

First, save the contents of your unsent email. Copy the message text into Notepad or another document if you don’t want to risk losing your work.

Close Outlook by clicking the X in the upper-right corner. Wait a few seconds, then open the Start menu, search for Outlook, and launch the application again.

Create a new email by selecting New Email. Enter your own email address in the recipient field, add a simple subject, and type a short test message.

Click Send and check whether the message reaches your inbox.

If the new email works, the problem may be related to the original message, its attachments, or its formatting. If the test email fails too, continue with the following steps.

2: Check Your Internet Connection and Outlook Status

Outlook needs a working connection to communicate with your email provider. If your connection is unstable or Outlook is offline, messages may remain stuck in the Outbox.

Open a web browser and visit a few websites to confirm that your internet connection is working. If pages aren’t loading, reconnect to Wi-Fi or restart your router.

Next, check Outlook’s connection status. In classic Outlook for Windows, look at the status bar near the bottom of the application. If it displays Working Offline or Disconnected, Outlook may not be connected to your mail server.

If you see Working Offline, open the Send/Receive tab and select Work Offline to turn the setting off, if that option is enabled. Wait for Outlook to reconnect.

If your account still appears disconnected, close and reopen Outlook. You can also check whether your email provider is experiencing a service interruption.

Once Outlook reconnects, open the unsent message and try sending it again.

3: Remove Large Attachments From the Email

Large attachments are a common reason an email won’t send. Your email provider may impose a message-size limit, and the actual size of an attachment can increase when it is encoded for email transmission.

Open the affected message in Drafts or the Outbox, depending on where it is stored. Review the attached files and check whether any are particularly large.

If the message contains a large video, ZIP archive, or several high-resolution images, remove one or more attachments and try sending the email again.

If you still need to share those files, upload them to a trusted cloud storage service, such as OneDrive, and include a sharing link in the email. Make sure the recipient has permission to access the files.

You can also compress suitable files into a ZIP archive, although compression won’t significantly reduce the size of every file type.

After reducing the message size, save the email and send it again. If it works, the attachment size or message contents may have caused the original problem.

4: Check the Message Formatting

Sometimes a particular email’s formatting, embedded images, or copied content can cause problems when Outlook tries to send it.

Open the affected message and copy its text into a new email. Re-enter the recipient’s address and subject, then paste the message content into the new draft.

If you’re copying formatted content from Microsoft Word, a website, or another application, try pasting it as plain text. This removes much of the original formatting that could be causing trouble.

In classic Outlook, you can change the message format using the Format Text tab. Try HTML or Plain Text, depending on the current format and your needs.

Keep the original draft until you confirm that the new message sends successfully. If the new email works, you can continue using the replacement message and recreate any necessary formatting.

If you still receive the error, move on to the next method.

5: Clear Stuck Messages From the Outbox

A message that remains stuck in the Outbox can sometimes interfere with later sending attempts.

Open Outlook and select the Outbox folder in the folder pane. If the folder isn’t visible, expand your mailbox folders.

Look for the message that failed to send. Open it and check whether Outlook displays the same error again.

If the message is still needed, save its contents and attachments before moving or deleting anything. You can then move the message to Drafts, if Outlook allows it, and create a fresh email from the saved content.

If Outlook is trying to send the same message repeatedly, switch to offline mode first in classic Outlook by selecting Send/Receive > Work Offline. Move the affected message out of the Outbox, then turn offline mode off and reconnect.

Be careful not to remove messages that are still needed. After Outlook reconnects, send a new test email to check whether the Outbox is working normally.

6: Start Outlook in Safe Mode and Disable Add-Ins

Outlook add-ins provide extra features, but a faulty or incompatible add-in can interfere with email operations. Starting Outlook in Safe Mode helps you determine whether an add-in is responsible.

Close Outlook completely. Press Windows + R to open the Run dialog box.

Type the following command and press Enter:

outlook.exe /safe

If Windows cannot find the command, Outlook may not be installed in a location available through the Run dialog. You can locate the Outlook application and start it with the Safe Mode option if supported.

If Outlook opens in Safe Mode, try sending a new test email.

If the email sends successfully, an add-in may be causing the problem. Close Safe Mode and reopen Outlook normally. In classic Outlook, select File > Options > Add-ins.

At the bottom of the window, find the Manage dropdown, select COM Add-ins, and click Go. Clear the checkboxes to disable the add-ins temporarily, then click OK.

Restart Outlook and test sending again. If the error disappears, enable the add-ins one at a time to identify the one causing the issue.

The menus may differ in the newer Outlook for Windows app, which doesn’t use the same COM add-in management interface.

7: Update Outlook and Repair Microsoft Office

An outdated Outlook installation or damaged Office components can cause unexpected errors. Installing available updates and repairing Office may help resolve the problem.

If you’re using classic Outlook, open the application and select File > Office Account. Under Product Information, look for Update Options and select Update Now, if available.

If you use the newer Outlook app, check for updates through the Microsoft Store or your organization’s supported update process.

If updating doesn’t help, close all Office applications. Open Settings > Apps > Installed apps in Windows 11, or Settings > Apps > Apps & features in Windows 10.

Find Microsoft 365 or your installed version of Microsoft Office. Select the three-dot menu or the application entry, then choose Modify if available.

Start with Quick Repair and follow the instructions. This process repairs common Office problems without requiring a full online download.

If the error continues, consider Online Repair. This option takes longer and may require an internet connection. Save your work and close Office apps before starting.

When the repair finishes, reopen Outlook and try sending the email again.

8: Create a New Outlook Profile

If the error continues after trying the earlier fixes, your Outlook profile may be damaged. Creating a new profile can help determine whether the issue is tied to the existing configuration.

Close Outlook. Open the Windows Control Panel and search for Mail. If you don’t see the option, change the Control Panel view to show all items.

Open the Mail Setup dialog and select Show Profiles. Click Add, enter a name for the new profile, and follow the instructions to add your email account.

After configuring the account, select the option to prompt for a profile when Outlook starts, if available. Open Outlook and choose the new profile.

Allow Outlook time to synchronize your mailbox. Then send a test email.

Before removing the old profile, make sure you can access all your important messages and data. Accounts using Exchange or IMAP typically synchronize server-stored mail, but locally stored PST files and other local-only data may require separate handling.

If the new profile works, you can continue using it and investigate transferring any local data you still need.

9: Test Outlook on the Web

Finally, use Outlook on the web to check whether the problem is limited to the desktop application.

Open your email provider’s official website in a browser and sign in to the same account. For a Microsoft 365 work or school account, use the webmail address provided by your organization. For a personal Outlook.com account, visit Outlook.com.

Create a short test email and send it to your own address.

If the message sends successfully on the web but fails in the desktop app, the issue is more likely related to the local Outlook installation, profile, or configuration.

If the message also fails on the web, check your mailbox storage, account restrictions, recipient address, and any error details provided by your email service. For work or school accounts, your administrator may need to check mail flow or sending restrictions.

This test helps you narrow down the cause instead of repeatedly changing settings that may not be responsible.

FAQs

1. Why does Outlook say “Cannot send this item”?

The error can occur because of a problematic email draft, large attachments, formatting issues, faulty add-ins, a damaged Outlook profile, or a connection problem. The exact cause depends on when the error appears.

2. Will repairing Outlook delete my emails?

A Quick Repair generally isn’t intended to delete your emails. However, it’s wise to back up important local Outlook data before making major changes, especially if you use PST files or have messages stored only on your computer.

3. Why can I receive emails but not send them?

Receiving and sending use different mail operations. You may be able to receive messages while outgoing mail is blocked by account settings, server restrictions, authentication issues, or a stuck Outbox message.

4. Does this error happen in both Windows 10 and Windows 11?

Yes. It can occur in Outlook on both operating systems. The exact menus may differ depending on whether you’re using classic Outlook or the newer Outlook for Windows app.

5. What should I do if none of these fixes work?

Test your account through Outlook on the web, note any additional error messages, and contact your email provider or IT administrator if needed. For a work account, server-side restrictions may require an administrator to resolve.