Using classic Outlook for Windows in business environments
Hello,
As the forum’s AI recommended, checking the sender’s non-delivery report (NDR) and SMTP delivery logs is the right starting point. However, the information provided does not yet establish where delivery is failing.
Could you confirm whether your mailboxes are hosted in Microsoft 365/Exchange Online and whether incoming mail passes through a third-party email security gateway first? Also, are the “inbound logs” you checked Exchange Online message trace results or logs from another mail server/gateway?
If you use Exchange Online, please work with your email administrator and the vendor’s mail administrator on these checks:
- Capture one fresh delivery attempt. Ask the vendor to send a new test message to an affected recipient and record the time and time zone. Their administrator should check the actual outbound sending IP, destination mail server, and SMTP response, or confirm whether the message remains queued. If there is no NDR, ask them to check the outbound delivery logs for that test.
- Trace the same message on your side. In the Exchange admin center, go to Mail flow > Message trace. Search using the recipient and the test’s time range, select the matching time zone, and include all delivery statuses. Open any matching result to inspect its events. See Microsoft’s message trace instructions. Microsoft states that messages typically take 5–10 minutes to appear in trace data. Also, connection-filter events, such as blocked IP addresses, are not traceable. Therefore, no matching trace result alone does not prove that the sender never contacted Microsoft 365. See Message trace FAQ. If you use an upstream email gateway, have its administrator check receipt and onward delivery for the same test.
- Choose the fix based on the actual error. Microsoft maintains its own sending-IP blocklist, so a clean public blocklist result does not rule out a Microsoft IP block. However, an IP block has not been confirmed in this case. If the NDR contains 550 5.7.606-649 with “banned sending IP,” the vendor should follow Microsoft’s IP delisting procedure. For 5.7.511, Microsoft instead instructs the sender to contact delist@microsoft.com with the full NDR code and sending IP. These procedures apply only when the corresponding error is present. See Microsoft’s delisting instructions.
I recommend identifying the delivery failure before making further allow-list or authentication changes.
Please confirm your mail hosting/gateway setup and share the SMTP error code and accompanying error text, if available. Remove email addresses, IP addresses, message IDs, and other identifying details before posting publicly.