New Outlook for Mac Emails Stuck in Outbox – Troubleshooting Guide

Outlook is a reliable way for computer users to send and receive emails. However, many users are currently experiencing the issue of new Outlook for Mac emails stuck in Outbox when trying to send messages. If you’re facing the same problem, there’s no need to worry, this blog post will help you understand and fix it.
There can be several reasons why Outlook for Mac emails get stuck in the Outbox. In this article, we’ll explore the possible causes along with effective solutions to resolve the issue quickly. Let’s get started.
Section 1. Key Reasons Behind New Outlook for Mac Emails Stuck in Outbox
“Email stuck in Outbox” on Mac is a common issue that can happen for multiple reasons. If you’re dealing with new Outlook for Mac emails stuck in Outbox, understanding the root cause is the first step toward fixing it. Below are the most common reasons along with simple explanations and fixes.
Reason 1. Large Attachment Files
One major cause of this issue is sending emails with large attachments that exceed the mail server’s allowed size limit. When this happens, the email may fail to send and remain stuck in the Outbox.
Solution: Try removing the attachment or moving the email to the Drafts folder. You can then compress, resize, or delete the file before sending it again.
Reason 2. Opening the Email Before It Sends
If you open an email while it’s still in the Outbox, Outlook may mark it as “read” and interrupt the sending process. A common sign of this is that the email subject is no longer in bold.
Additionally, certain Outlook add-ins like BCM or Social Connector can interfere with the sending process.
Solution: Avoid opening emails before they are sent. Also, consider disabling or uninstalling unnecessary add-ins.
Reason 3. Incorrect or Updated Password
Using an incorrect or recently changed password can prevent Outlook from sending emails, causing them to remain in the Outbox.
Solution: Double-check your email account password. If you’ve recently changed it, make sure the updated password is entered correctly in Outlook.
Reason 4. Improper Account Authentication Settings
Incorrect account or server settings can also lead to emails getting stuck in the Outbox.
Solution (Steps to Verify Settings):
- Open Outlook and go to the File tab, then select Account Settings.
- Navigate to the Tools menu, click Account Settings, and choose your email account.
- Double-click your account and go to the Outgoing Server tab. Ensure all details match those provided by your email service provider.
Note: Avoid selecting “regular secure password authentication.”
- Go to the Advanced tab and verify the outgoing server (SMTP) port number.
Note: Port 25 is commonly used for SMTP accounts.
Reason 5. Default Account Not Set Properly
Another possible cause behind Outlook for Mac email stuck in Outbox is when no default email account is selected. This often happens when the account is set up using a pre-configured script by an administrator.
Solution (Steps to Set Default Account):
- Open Account Settings to check your configured accounts.
- Click on File and select Account Settings.
If no account is marked as default, select your preferred account and set it as the default one.
Section 2. Effective Tips to Fix New Outlook for Mac Emails Stuck in Outbox
If the above reasons apply to your situation, try the following solutions to resolve the issue.
Solution 1. Change DNS Settings on Mac
Sometimes, network-related issues can prevent emails from sending, causing them to remain in the Outbox. Updating DNS settings can help improve connectivity.
- Go to the Apple menu, open System Preferences, and select Network.
- Choose your active network connection and click on Advanced.
- Navigate to the DNS tab and click the (+) icon to add a new DNS server.
Once you update the DNS settings, your network performance may improve, and the Outlook Outbox issue should be resolved.
Solution 2. Ensure Outlook is Connected to the Internet
A poor or disconnected internet connection can prevent Outlook from sending emails. When Outlook is offline, you may see statuses like Disconnected or Trying to connect.
Fix: Check your internet connection and make sure Outlook is online. Once the connection is stable, your emails should send without any issues.
Solution 3. Force Quit and Restart Outlook
Restarting Outlook can help fix temporary glitches causing emails to remain in the Outbox.
- Press Option + Command + Esc keys together.
- Select Outlook (or Mail) from the list and click Force Quit.
- Reopen Outlook and check if the issue is resolved.
Solution 4. Check the Attachment File Size
Even with a stable internet connection, large attachments can block emails from being sent.
Fix: Review the file size of attachments. If the file is too large, reduce its size, compress it, or remove it before sending the email again.
Solution 5. Use the Correct Password
If you’ve recently changed your email password, Outlook may still be using the old one, causing sending failures.
- Go to File and click Account Settings.
- Select Account Settings again.
- Choose your email account and click Change.
- Enter the updated password under Login Information.
- Restart Outlook and verify if the issue is fixed.
Solution 6. Check Outgoing Server (SMTP) Settings
Incorrect SMTP settings can also lead to emails getting stuck in the Outbox.
- Open Mail and go to Preferences, then click Accounts.
- Select your email account.
- Go to Server Settings, click the outgoing account menu, and select Edit SMTP Server List.
Make sure all the server details match those provided by your email service provider.
Section 3. What If None of the Solutions Work?
If none of the above methods help resolve the issue of Outlook for Mac email stuck in Outbox, it is recommended to secure your data by creating a complete backup of your Outlook account and migrating it to another platform.
This can be efficiently done using the CubexSoft Mac OLM Converter tool. This software allows you to back up Mac Outlook data files into multiple formats such as HTML, PST, PDF, EML, DOC, MBOX, ICS, CSV, MHT, XPS, etc. Additionally, it supports direct migration to email services like Gmail, Yahoo, Office 365, IMAP, Thunderbird, Zimbra, Hosted Exchange Server, and so on.
The tool comes with a simple and user-friendly interface, making it suitable for both technical and non-technical users. It also offers advanced features that help complete the conversion process quickly and accurately. A free demo version is available, allowing users to convert a limited number of files before purchasing.
Final Words
In this article, we have explained the causes and solutions for the Microsoft Outlook for Mac emails stuck in Outbox issue. You can try the basic as well as advanced methods to fix the problem.
If the issue still doesn’t get resolved, it is better to back up your Mac Outlook data and move it to a safe location or another email server. For this, you can use the OLM Converter for Mac.
Also, keeping a regular backup is important to avoid data loss and ensure your email work runs smoothly in the future.
