Stuck in the Outbox? Here’s the Fix!

Nothing is more frustrating than hitting “Send” and watching your email sit in the Outbox forever. Whether you’re using Outlook or Gmail, email delivery issues can happen due to poor internet connection, incorrect settings, or email provider restrictions.

In this guide, we’ll cover step-by-step solutions to fix email sending issues in Outlook (Windows & Mac) and Gmail so you can get back to business.

Step 1: Check Your Internet Connection

Before troubleshooting deeper, ensure your device is connected to a stable internet network:

✅ Try opening a website in your browser.

✅ Restart your Wi-Fi router if needed.

✅ Switch from Wi-Fi to mobile data (on mobile devices) to test.

If the internet is working fine, move on to the next steps.

Fixing Email Sending Issues in Outlook

1. Check If Outlook Is Offline

Outlook might be in Offline Mode, preventing emails from sending.

✅ For Windows:

1. Open Outlook.

2. Go to the Send/Receive tab.

3. If Work Offline is highlighted, click it to disable.

✅ For Mac:

1. Open Outlook.

2. Click Outlook > Work Offline (uncheck if enabled).

2. Restart Outlook and Your Computer

Simply restarting Outlook or your PC/Mac can refresh your email settings and fix sending issues.

1. Close Outlook completely.

2. Restart your computer.

3. Reopen Outlook and try resending the email.

3. Check Email Account Settings

If Outlook isn’t configured correctly, emails won’t send.

1. Go to File > Account Settings > Account Settings.

2. Select your email account and click Change.

3. Verify:

• Incoming Mail Server & Outgoing Mail Server (SMTP) are correct

• Username & Password are entered correctly

• Require authentication for SMTP is enabled

💡 Tip: If unsure, check with your email provider for correct settings.

4. Clear the Outbox and Resend Emails

Sometimes, an email gets stuck in the Outbox, preventing other messages from sending.

1. Go to the Outbox folder.

2. Right-click the stuck email and select Delete.

3. Try sending a new email to see if the issue is resolved.

5. Increase Server Timeout Settings

If emails with large attachments aren’t sending, you may need to increase server timeout settings:

1. Go to File > Account Settings > Account Settings.

2. Select your email account and click Change > More Settings.

3. Go to the Advanced tab.

4. Increase the Server Timeout to a longer duration.

5. Click OK > Next > Finish and restart Outlook.

6. Disable Add-Ins That May Be Blocking Emails

Outlook add-ins (especially third-party security software) can interfere with email sending.

1. Open Outlook.

2. Click File > Options > Add-ins.

3. Click Go (next to “Manage COM Add-ins”).

4. Uncheck all unnecessary add-ins and click OK.

5. Restart Outlook and test sending an email.

7. Check Your Antivirus or Firewall Settings

Some antivirus programs block outgoing emails due to security restrictions.

✅ Temporarily disable your antivirus or firewall and test if Outlook sends emails.

✅ If this fixes the issue, whitelist Outlook in your antivirus settings.

8. Update or Reinstall Outlook

If all else fails, update Outlook to the latest version or reinstall it.

• Windows: Go to File > Office Account > Update Options > Update Now.

• Mac: Open App Store > Updates and install any pending Outlook updates.

Fixing Email Sending Issues in Gmail

1. Check Gmail’s Outbox (For Mobile Users)

If using the Gmail app, emails might be stuck in the Outbox due to connectivity issues.

✅ Steps to Check & Resend Emails in Outbox:

1. Open Gmail.

2. Tap the Menu (☰) > Outbox.

3. If you see unsent emails, tap on them and hit Send again.

2. Check Your Gmail Storage

Google limits email sending if your storage is full.

✅ Check Storage Usage:

1. Visit Google Storage.

2. If it’s full, delete large emails or Google Drive files.

3. Check Gmail SMTP Settings (For Third-Party Clients)

If using Gmail in Outlook, Apple Mail, or Thunderbird, verify SMTP settings:

• SMTP Server: smtp.gmail.com

• Port: 465 (SSL) or 587 (TLS)

• Requires Authentication: Yes

• Username: Your full Gmail address

• Password: Your Gmail password or App Password (if 2FA is enabled)

4. Disable Gmail Labs Features (For Web Users)

Experimental Gmail Labs features may interfere with email sending.

✅ Disable Gmail Labs Features:

1. Open Gmail in a browser.

2. Click Settings (⚙️) > See All Settings > Advanced.

3. Disable any experimental features.

4. Click Save Changes and restart Gmail.

5. Check for Google Account Security Blocks

Google may block your emails if it detects “suspicious activity.”

✅ Check for security alerts:

1. Visit Google Security.

2. Look for “Blocked Sign-in Attempt” notifications.

3. Follow the instructions to approve the login.

💡 Tip: If using a third-party email client, enable “Less Secure Apps” or generate an App Password in Google Account Settings > Security.

6. Clear Browser Cache (For Gmail Web Issues)

If Gmail isn’t sending emails in a browser, clear your cache and cookies:

✅ Chrome Users:

1. Press Ctrl + Shift + Delete.

2. Select Cached Images & Files and Cookies.

3. Click Clear Data.

4. Restart the browser and test Gmail again.

Get Back to Sending Emails!

If your emails aren’t sending, follow these quick fixes:

✔ Check internet connection

✔ Clear Outbox & resend email

✔ Update SMTP settings (Gmail users)

✔ Increase server timeouts (Outlook users)

✔ Disable antivirus/firewall if blocking emails

✔ Restart your device & email client