How to Fix Emails Stuck in Outbox – Step by Step Outlook Solution

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Key Takeaways

• • One effective approach to resolve emails stuck in the Outbox is by removing any large attachments that may be hindering the email from sending. Large files can often exceed the sending limit, causing the email to remain unsent in the Outbox.
  • Another solution involves restarting Outlook in Safe Mode. This can help bypass issues with add-ins or configurations that might be causing problems with email sending, thus potentially freeing up the stuck email.
  • Ensuring proper Email Server Authentication settings can also rectify issues related to emails stuck in the Outbox. Incorrect authentication settings may prevent emails from being sent, so verifying these settings can lead to a successful resolution.

Common Symptoms of Stuck Emails

When an email gets stuck, the most telltale symptom is your message lurking in the Outbox with no status change. You might notice that despite multiple attempts to send, the email remains stationary. Other common signs include a lack of that ‘Sent’ confirmation, inability to delete the immobile email, or Outlook might display error messages indicating a failure to complete the send/receive cycle. Additionally, if your recipients report not receiving emails that appear to have been sent, that could also be a symptom of the issue.

Quick Solutions to Resolve Stuck Emails

Checking and Updating Email Settings

To ensure smooth email transmission, keeping your email settings up to date in Outlook is crucial. They are the roadmap that guides your emails out of the Outbox and into the intended inboxes. Start by opening the Account Settings window in Outlook – the steps may vary based on your Outlook version, but generally, it involves:

STEP 1: Clicking on the File tab.

STEP 2: Click on the Account Settings. Here, you can verify your outgoing and incoming server information, port numbers, and encryption methods.


If your password has recently changed, it’s essential to update this information in Outlook. Select your email account and click ‘Change…’ to update your password, ensuring it matches the one you use to log into your email on the web. After updating, don’t forget to click ‘Next’ and ‘Finish’ to save these new credentials.

Removing Large Attachments Before Sending

Trying to send an email with attachments that are too bulky can often lead to them being trapped in your Outbox. To avoid this, you can manage large files efficiently. Start by checking the size of the attachments before hitting send; if they’re too large, consider compressing them into a zip file to shrink the byte count. Better yet, use cloud services such as Dropbox or Google Drive, and include the link to the file in your email instead of attaching it. Not only does this bypass the size limitations, but it also leads to a more organized and professional email interaction.

If you do find an email stranded in the Outbox due to a large attachment, don’t worry. Take Outlook offline, so it stops attempting to send, then move the email to Drafts. From there, you can easily remove or replace the attachment before sending it off again.

Advanced Troubleshooting Methods

Running Outlook in Safe Mode to Identify Issues

When you’re dealing with a stubborn email that refuses to leave your Outbox, running Outlook in Safe Mode can be a game-changer. This mode allows Outlook to run without any add-ins or extensions, which can sometimes interfere with email sending. To start Outlook in Safe Mode, press the Windows key and ‘R’ at the same time, then type outlook /safe and press ‘OK.’ If your email sends successfully while in Safe Mode, you’ve found a clue that an add-in may be the culprit.

For a quick Safe Mode access, hold the ‘Ctrl’ button while double-clicking the Outlook shortcut and continue holding until you’re prompted to open in Safe Mode. Click ‘Yes,’ and you’re in. This is an excellent initial diagnostic tool to identify any obvious issues that might be affecting Outlook’s performance.

Cleaning Up Your Outlook Profile

Sometimes, the solution to freeing those stuck emails lies in decluttering your Outlook profile. Just like tidying up a messy room, cleaning up your Outlook can improve its functionality. Start this process by archiving old emails to keep your inbox size manageable. Next, review any stored email addresses that may be outdated or incorrect in your auto-complete list – this can prevent issues related to sending emails to incorrect recipients.

Additionally, cleaning your Sent Items folder can help, especially if it’s loaded with old conversations that are clogging the system. Carefully deleting what you no longer need can not only resolve issues but also speed up Outlook’s performance.

Lastly, consider creating a new profile if these attempts don’t work. A fresh start for Outlook might be just what you need to get things back on track.

Dealing with Email Server Challenges

Verifying Email Server Authentication

It’s vital to check that your email server authentication settings are correctly configured, as failing to do so can certainly lead to emails remaining trapped in your Outbox. To do this, dive into Account Settings once more.

STEP 1: Go to File > Account Settings > Manage Profiles.

STEP 2: Click on Email Accounts > Double-click on your email account.

Under the ‘Outgoing Server’ tab, ensure that ‘My outgoing server (SMTP) requires authentication’ is checked. If your email server has specific authentication requirements, like using the same settings as your incoming mail server, you need to make sure those are selected too.


Don’t forget, every email service provider has their own set of rules for server authentication, so if you’re unsure, it’s best to check with your provider for the correct settings to avoid sending issues.

Preventative Measures for a Smoother Outlook Experience

Regularly Update Outlook and Office Apps

Keep your Outlook and the rest of your Office apps fresh and up-to-date to steer clear of various issues, including those pesky emails sticking in the Outbox. Regular updates bring not just new features but also key bug fixes and improvements that can enhance your user experience. To update, open Outlook, head to the ‘File’ tab, slide into ‘Office Account,’ and hit ‘Update Options.’ Select ‘Update Now’ and let the magic happen as the latest software developments download and install.

It’s worth waiting for this little tech-refresh – the updates could very well iron out any kinks keeping your emails captive in the Outbox. Plus, you’ll also gain from the added security patches that protect your digital correspondence from prying eyes and other threats.

Special Solutions for Persistent Problems

Creating a New Outlook Data File (.pst)

If your usual troubleshooting methods haven’t made a dent, creating a new Outlook Data File (.pst) can sometimes work wonders. This process gives you a fresh data file to work with, potentially free from corruption or other problematic snags.

To create this lifeline, head to File > Account Settings > Account Settings… > Data Files > Add… in Outlook 2010 – 365. If you’re still using Outlook 2007 or older, go to File > New > Outlook Data File… . Choose a convenient location to save the new file and name it (“Outlook_New.pst”, perhaps).

Next, make this new file your default delivery location—the emails you send will start going into this ‘new’ Outbox. If your stranded messages sail smoothly from here, it might be time to consider transferring data from the old .pst file and sticking with the new one.

Remember, though, this is like moving into a new house; it takes some setting up. But once you’re settled, the email flow should be much smoother.

Tips to Prevent Emails from Getting Stuck

Enable Send Immediately When Connected Option

To help your emails take flight as soon as you’re online, you’ll want to ensure the ‘Send immediately when connected’ option is active in Outlook. This setting is like giving emails a green light to zoom off the moment you click ‘send,’ provided you have an Internet connection.

For Outlook 2010 and later, including versions like 2016, 2019, 2021, and even 2022, do this:

STEP 1: Click on the File tab at the top, then select Options.

STEP 2: In the Outlook Options dialog box, click on Advanced.

STEP 3: Scroll down to the Send and receive section and there, make sure the ‘Send immediately when connected’ checkbox is ticked.

STEP 4: Finish up by clicking OK.

For Outlook 2007 and 2003 users:

STEP 1: Go to the Tools menu and click Options.

STEP 2: When the Options dialog box opens, click the Mail Setup tab.

STEP 3: Look for the Send/Receive section, and again, ensure the ‘Send immediately when connected’ checkbox is selected.

STEP 4: Click OK to save your settings.

Simple as that! With this setting enabled, your emails should shoot through the digital skies without stalling in the Outbox.

Set the Correct Default Account

Having multiple email accounts and not setting the correct one as the default can sometimes lead to email traffic jams in your Outbox. It’s like trying to send mail from a post office that doesn’t know your return address. To streamline the process, check which account Outlook is using by default.

Here’s how:

STEP 1: Open Account Settings in Outlook. In newer versions, it’s under the File > Info tab, while in older editions, you might find it under Tools.

STEP 2: Navigate to the Email tab and skim down to see the message “send from this account by default” next to one of your email accounts.

STEP 3: If the status quo isn’t what you’re after, simply click on the account you’d like to be the star of the show, then hit the ‘Set as Default’ button.

If you’ve recently changed your account password, don’t forget to update this in Outlook. Otherwise, you could be left wondering why those letters are just lounging in the Outbox instead of making their way to the inbox-party.

Resourceful Strategies for Last Resort

Managing Outlook Privacy Settings

In more obscure cases, tweaking Outlook’s privacy settings could be the key to unstick those stubborn outbox emails. It’s like setting up the correct boundaries in your digital space to allow for a free flow of communication. To manage these settings, take a trip to the File tab > Options > Trust Center. Here, you’ll confront a myriad of privacy options related to automatic downloads, email security, and add-ins.

Take caution while here, as an overzealous change could impact functionality. It’s a good practice to revamp one setting at a time and monitor the outcome. This way, you maintain control over your data while troubleshooting Outlook’s performance issues.

FAQs About Outlook Emails Stuck in Outbox

Why are emails not sending from my Outbox in Outlook?

Outlook emails might stay put in your Outbox instead of soaring to their designated inboxes for several reasons. It could be a case of incorrect email settings, an unreliable internet connection, or trouble with the email server. Be sure to double-check your settings, test your network strength, and verify server status to kick those emails back into the sending stream.

What could be causing attachments to prevent email delivery?

Attachments can block email delivery if they’re too large, exceed recipients’ size limits, or if they’re in a format your email server doesn’t fancy. To avoid such issues, compress your files, use a cloud-sharing service, or confirm the allowed attachment types and sizes with your email provider.

How can I prevent Outlook from working offline unintentionally?

To stop Outlook from slipping into the offline mode when you’re not expecting it, keep an eye on the status bar at the bottom of the window for any ‘Working Offline’ messages. If it happens, simply go to the Send / Receive tab and toggle the ‘Work Offline’ option to reconnect. Additionally, make sure your internet connection is stable to avoid unexpected switches to offline mode.