Microsoft Outlook / Hotmail / Live / MSN / Exchange Online error guide

Microsoft Outlook / Hotmail / Live / MSN / Exchange Online SMTP 550 5.4.300: Delivery Expired

Microsoft Outlook / Hotmail / Live / MSN / Exchange Online SMTP 550 5.4.300 usually means routing. Learn whether to retry, suppress the recipient, or fix sender setup.

Quick summary

Primary code
550 5.4.300
Provider coverage
Microsoft Outlook / Hotmail / Live / MSN / Exchange Online
Primary action
Do not retry unchanged

How to handle 550 5.4.300

Match the provider, SMTP stage, endpoint, and diagnostic wording first, then use the checks below to decide whether to retry, suppress the recipient, or fix sender setup.

Microsoft mail servers 550 5.4.300

Routing

Do not retry unchanged

The receiving service refused the route, connector, or relay path. The recipient may still be valid, so fix routing before making a suppression decision.

Decision

Review the full SMTP reply before retrying.

Confidence: high. Recipient validity: unknown.

Match this reply

SMTP stage
Any SMTP stage
Endpoint
Inbound MX
Message expired

Start here

  1. 1

    Check MX records, forwarding paths, and connector configuration for loops or relay denial.

  2. 2

    Retry only after the routing path has been corrected.

Confirm the cause

  1. Match provider, SMTP stage, endpoint, reply code, enhanced code, and diagnostic text.
  2. Run the sender, recipient, DNS, and content checks that match the diagnostic wording.
  3. Test with one recipient before retrying bulk traffic.

App handling

  • Route to manual review or a conservative fallback classification.
  • Do not suppress the recipient from this rule unless a later bounce gives stronger recipient evidence.
  • Limit automated retries until the provider-specific cause is understood.

Avoid

  • Do not decide from the SMTP code alone.
  • Do not suppress unless the provider-specific evidence points to an invalid recipient.
  • Do not retry high-volume traffic before you understand the diagnostic text.
Common causes
  • The provider-specific diagnostic text matches this class of failure.
  • The same SMTP code may have another meaning when the provider, stage, or endpoint differs.
  • Sender setup, recipient status, and provider policy should all be checked before taking irreversible action.
Developer details
Fields to log
raw SMTP replyremote MX or hostSMTP stagereply codeenhanced codeprovidermatched rule idrecipientsending domaindecisiontimestampsource IPconnectorTLS result
Classifier evidence
Specific cause
delivery expired
Evidence
official

Not sure this is the right match?

Paste the full SMTP reply into the lookup tool. The classifier uses provider, endpoint, SMTP stage, reply code, enhanced code, token, and diagnostic text.

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