Apple mail not sending emails with attachments

Frustrating! Don't worry, I'm here to help you troubleshoot the issue. Here are some steps to help you resolve the problem of Apple Mail not sending emails with attachments:

  1. Check the attachment size: Make sure the attachment is not too large. Apple Mail has a file size limit of 20 MB per attachment. If your attachment is larger than that, try compressing it or breaking it down into smaller files.
  2. Verify the attachment type: Ensure that the attachment is a valid file type that Apple Mail supports. Common file types like PDF, DOCX, XLSX, and JPEG are usually okay. If you're trying to send a file with a different extension, try converting it to a supported format.
  3. Check the email account settings: Ensure that your email account settings are correct. Go to Mail > Preferences > Accounts, and verify that your account is set up correctly. Make sure the "Outgoing Mail Server" is set to the correct server and port.
  4. Disable any third-party plugins: Sometimes, third-party plugins can interfere with Apple Mail's functionality. Try disabling any plugins you have installed and see if the issue persists.
  5. Clear the Mail cache: Clearing the Mail cache can sometimes resolve issues with attachments. To do this, go to Mail > Preferences > General, and click "Reset" next to "Reset Mailbox Database."
  6. Check for conflicts with other apps: If you're using other apps that also handle email attachments, try closing them or disabling their email features to see if it resolves the issue.
  7. Try sending a test email: Send a test email with a small attachment to see if it goes through successfully. If it does, then the issue might be specific to the attachment you're trying to send.
  8. Check for software updates: Ensure that your Mac and Apple Mail are up to date. Sometimes, updates can resolve issues like this.
  9. Try using a different email client: If none of the above steps work, try using a different email client like Microsoft Outlook or Mozilla Thunderbird to see if the issue persists.
  10. Contact your email provider: If none of the above steps work, it's possible that the issue is on the server-side. Contact your email provider's support team to see if they're experiencing any issues with attachments.

If you've tried all of these steps and the issue still persists, feel free to provide more details about your setup and the error message you're seeing, and I'll do my best to help you troubleshoot further!