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5 min read

Why Emails Won't Send

Outgoing email failures usually involve server settings, authentication or size limits.

At a glance

  • →Authentication settings cause more send failures than server outages.
  • →Attachments often exceed limits after encoding.
  • →Webmail tests whether the account itself is healthy.

Sending an email is a conversation between your app and an outgoing mail server. Your app must know the correct address, the correct port, and the correct password or token. If any of those is wrong, the server refuses the message and it sits in the outbox.

Authentication is the most common modern cause. Many providers no longer accept a plain password and require an app-specific password or an OAuth sign-in. After a password change, the app often keeps trying the old one until the account is updated.

Size limits create a different symptom. Attachments that look small on your device can be much larger after encoding, and many servers reject messages above a few megabytes. The email stays in the outbox without a clear explanation.

Connection security settings also matter. Servers now expect encrypted connections on specific ports. A setting that worked years ago may be rejected today because the server no longer allows older, unencrypted methods.

Common causes

  • Wrong outgoing server address or port
  • Password or app-specific password needs updating
  • Attachment larger than the provider allows
  • Security setting mismatch with the server
  • Account temporarily blocked for suspicious activity

Troubleshooting tips

  1. 1Check the provider's current server settings and compare them with the app.
  2. 2Generate a new app-specific password if the provider requires one.
  3. 3Reduce attachment size or use a cloud link instead.
  4. 4Try sending from the provider's web interface to test the account.
  5. 5Enable the recommended encryption setting for the server.

Key takeaways

  • • Authentication settings cause more send failures than server outages.
  • • Attachments often exceed limits after encoding.
  • • Webmail tests whether the account itself is healthy.

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