Diagnose email delivery problems

A structured investigation for mail that bounces, disappears or lands in spam — from reading headers to checking reputation.

AdvancedAbout 40 minutes9 steps

What you’ll need

  • A test message that didn’t arrive properly, or its bounce
  • A Gmail or Outlook.com account to test with
  • DNS lookup tools

Delivery problems have many possible causes. This tutorial narrows them down in order, so you fix the actual cause rather than guessing.

Steps

  1. Step 1: Classify the problem

    Pick one: the app won’t send (Can’t send email: how to fix outgoing mail), it bounces (continue), it vanishes (continue), or it arrives in spam (continue from step 3).

  2. Step 2: Read the bounce

    If there’s a bounce, find the status code and reason. 5.7.x codes usually mean authentication or policy; listed at means a blocklist; user unknown means a wrong address. Understanding email bounce messages

  3. Step 3: Send a controlled test

    Send a short plain message, no links or attachments, from the affected mailbox to your Gmail test account. Plain content rules out content filtering.

  4. Step 4: Read the authentication results

    In Gmail, Show original. Record SPF, DKIM and DMARC results. Anything other than PASS: fix it first with Set up SPF, DKIM and DMARC.

  5. Step 5: Check the headers for the sending path

    In the original message, read the Received: lines from the bottom up. The first one added by your server shows the sending IP. Confirm mail left through your Traxio server rather than another service.

  6. Step 6: Check reputation

    Look up the sending IP and your domain on a multi-blocklist checker. Note which lists, if any. Email blacklists (blocklists): how to check and what to do

  7. Step 7: Test with content

    Send your real message — with its links, images and signature — to the same test account. If the plain test lands in the inbox but the real one doesn’t, the content is the problem: links, a URL shortener, a heavy image or wording.

  8. Step 8: Check for account compromise

    Look in the mailbox’s Sent folder and your forwarders for anything you didn’t create. My email account is sending spam

  9. Step 9: Escalate with evidence

    If authentication passes, content is clean and the server IP is listed on a major blocklist, send the help desk the bounce, the headers and the list name.

Check it worked

You can state which of these is the cause — authentication, content, reputation, recipient address or account compromise — and the controlled test now reaches the inbox.

If something goes wrong

What happensWhat to do
Only Microsoft addresses affectedMicrosoft filters heavily on reputation. Keep authentication perfect and ask recipients to mark you as safe while reputation builds.
Only website forms affectedThe form sends unauthenticated or with the visitor as From. Sending email from your website reliably

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