office 365 Failed to send a test message using SMTP Service

Situation: The client has QNAP storage. They can’t send notification with this error: Failed to send a test message using SMTP Service.

Troubleshooting: 1. SMTP settings is correct and test is fine.

Device or Application settingValue
Server/smart hostsmtp.office365.com
PortPort 587 (recommended) or port 25
TLS/StartTLSEnabled
Username/email address and passwordEnter the sign in credentials of the hosted mailbox being used

2. However, test sent to Recipient failed.

3. We find Microsoft article, “How to set up a multifunction device or application to send email using Microsoft 365 or Office 365” mentioned: “Option 1 (recommended): Authenticate your device or application directly with a Microsoft 365 or Office 365 mailbox, and send mail using SMTP AUTH client submission. This option is not compatible with Microsoft Security Defaults or multi-factor authentication (MFA). If your environment uses Microsoft Security Defaults or MFA, we recommend using Option 2 or 3 below”.

$. the option 2 and option 3 are “Option 2: Send mail directly from your printer or application to Microsoft 365 or Office 365 (direct send)” and “Option 3: Configure a connector to send mail using Microsoft 365 or Office 365 SMTP relay”.

4. We use option 2 fixes the problem. Here is the settings

Device or application settingValue
Server/smart hostYour MX endpoint, for example, contoso-com.mail.protection.outlook.com
PortPort 25
TLS/StartTLSEnabled
Email addressAny email address for one of your Microsoft 365 or Office 365 accepted domains. This email address does not need to have a mailbox.

We recommend adding an SPF record to avoid having messages flagged as spam. If you are sending from a static IP address, add it to your SPF record in your domain registrar’s DNS settings as follows:

DNS entryValue
SPFv=spf1 ip4:<Static IP Address> include:spf.protection.outlook.com ~all

Please refer to this how to:

How to setup Notification on QNAP

Published by

Bob Lin

Bob Lin, Chicagotech-MVP, MCSE & CNE Data recovery, Windows OS Recovery, Networking, and Computer Troubleshooting on http://www.ChicagoTech.net How to Install and Configure Windows, VMware, Virtualization and Cisco on http://www.HowToNetworking.com

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