How to Fix Emails That Won't Send

Difficulty: Easy

Time needed: 5-10 minutes

What you'll need: Access to your email account

Step 1: Check your internet connection

Open a web browser and try loading any website. If it doesn't load, fix your internet connection first — emails can't send without internet.

Step 2: Check the attachment size

Most email providers have limits on attachment sizes:

Gmail: 25 MB
Outlook: 20 MB
Yahoo: 25 MB

If your attachments are too large, use Google Drive, OneDrive, or Dropbox to share files via a link instead.

Step 3: Try sending from webmail

If you use an email app (Outlook, Apple Mail, Thunderbird), try sending from the web version of your email (gmail.com, outlook.com). If it works from the web, the problem is with your email app, not your account.

Step 4: Check your outbox

Outlook: Go to your Outbox folder. Open the stuck email, check for errors (wrong recipient, huge attachment), fix the issue, and try sending again
Apple Mail: Click the Outbox in the sidebar. Right-click stuck emails and try sending again
Gmail: Check the Drafts folder — failed sends sometimes end up there

Step 5: Verify your email settings

SMTP server: Make sure your outgoing mail server (SMTP) settings are correct. For Gmail: smtp.gmail.com, port 587, TLS enabled
Password: If you recently changed your email password, update it in your email app
Two-factor authentication: If enabled, you may need an App Password instead of your regular password for third-party email apps

Step 6: Check if your account is blocked

Some providers temporarily block sending if they detect unusual activity. Log into your email via a web browser and check for security alerts or verification prompts.

If that didn't work

Your email provider might be experiencing an outage. Check downdetector.com for your email service status. If it's a widespread issue, you'll just need to wait.

Pro tip

If you regularly send large files, set up a cloud storage account (Google Drive, Dropbox) and share links instead of attachments. It's faster, doesn't clog anyone's inbox, and avoids size limit issues entirely.