4.4.7
SMTPWARNINGNotableNetwork and RoutingHIGH confidence

Delivery time expired — message queued too long without delivery

Production Risk

High — a 4.4.7 indicates a serious delivery failure; the message was never received by the intended recipient.

What this means

The message has been in the sending MTA's queue for longer than the configured maximum queue lifetime without being successfully delivered. The sending MTA is giving up and generating a bounce notification.

Why it happens
  1. 1The destination server has been unreachable for an extended period.
  2. 2All delivery attempts over the queue lifetime have failed with transient errors.
  3. 3DNS resolution for the destination domain failed persistently.
How to reproduce

Sent message that could not be delivered; MTA queue lifetime (typically 4-5 days) has been exceeded.

trigger — this will error
trigger — this will error
# DSN bounce message to sender:
Subject: Delivery Status Notification (Failure)

Your message to user@example.com could not be delivered.
Final-Recipient: rfc822; user@example.com
Status: 4.4.7
Diagnostic-Code: smtp; 450 4.4.7 Message expired after X delivery attempts

expected output

DSN with status 4.4.7

Fix

Investigate why the destination was unreachable

WHEN After receiving a 4.4.7 bounce

Investigate why the destination was unreachable
# Check if destination MX is currently reachable:
dig MX example.com
telnet $(dig MX example.com +short | sort -n | head -1 | awk '{print $2}') 25
# Review MTA logs for all retry attempts:
grep 'example.com' /var/log/mail.log | grep -E '(connect|timeout|refused)'

Why this works

Understanding why delivery failed repeatedly helps determine whether to resend or treat as a permanent failure.

What not to do

Immediately resend the message after a 4.4.7 without investigating

If the destination was unreachable for days, the underlying issue may still persist. Investigate before resending.

Sources
Official documentation ↗

RFC 3463 — Enhanced Mail System Status Codes

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