Suped

What causes a 501 5.5.4 Invalid domain name error when sending emails to Office 365?

10 Marketer opinions5 Expert opinions5 Technical articles4 Resources

Summary

The 501 5.5.4 Invalid domain name error encountered when sending emails to Office 365 is a multifaceted issue with potential causes ranging from simple syntax errors in the recipient's email address to complex DNS misconfigurations and server-side problems. The root causes can be categorized into issues with the recipient's email address (invalid characters, syntax errors), DNS issues (missing/misconfigured MX records, incorrect PTR records), sender reputation (blacklisted IPs, poor reputation), server configuration (outdated TLS versions, firewall interference), and potential internal Microsoft infrastructure problems. Proper validation of email addresses, DNS record verification, sender reputation management, and troubleshooting using tools like telnet are critical in resolving this error.

Key findings

  • Recipient Address Syntax: Invalid characters, incorrect formatting, spaces, or typos in the recipient's email address are common causes.
  • DNS Configuration Issues: Missing or misconfigured MX records, incorrect reverse DNS (PTR) records, and general DNS lookup failures can lead to this error.
  • Sender Reputation Problems: Blacklisted IP addresses, poor sender reputation, or being flagged by anti-phishing filters can cause rejections.
  • Server-Side Configuration: Outdated TLS versions, local firewall interference, antivirus software, and incorrect HELO/EHLO greetings on the sending server can be factors.
  • Potential Internal Microsoft Issues: Internal infrastructure problems within Microsoft's email systems, such as nameserver misconfigurations, might contribute to the error.
  • Message Size Limits: Exceeding message size or recipient limits in Microsoft Exchange Online can also trigger the error.

Key considerations

  • Validate Recipient Addresses: Implement strict validation of recipient email addresses to prevent syntax errors.
  • Verify DNS Records: Regularly check MX records, PTR records, and other DNS settings to ensure proper configuration.
  • Manage Sender Reputation: Monitor IP addresses for blacklisting and maintain a positive sender reputation.
  • Update Server Configuration: Ensure that the sending server uses a supported TLS version, is not blocked by firewalls/antivirus, and has correct HELO/EHLO settings.
  • Troubleshoot with Telnet: Use telnet to manually connect to mail servers and diagnose connection issues.
  • Consider Bounce Message Source: Investigate the origin of bounce messages to better understand the error's context.
  • Check Message Size and Limits: Ensure the message size and number of recipients comply with Microsoft Exchange Online limits.

What email marketers say
10Marketer opinions

The 501 5.5.4 Invalid domain name error when sending emails to Office 365 can stem from various issues related to recipient address syntax, DNS configuration, sender reputation, authentication, and network settings. Problems range from invalid characters in the email address and missing or misconfigured DNS records (MX, PTR) to blacklisted IP addresses and incorrect SPF/DKIM settings. Local firewalls, antivirus software, and outdated TLS versions on the sending server can also contribute to this error. Testing with telnet and checking MTU sizes are useful troubleshooting steps.

Key opinions

  • Address Syntax: Invalid characters, spaces, or typos in the recipient's email address can trigger the error.
  • DNS Issues: Missing or misconfigured MX records, improper reverse DNS (PTR) records, and DNS server unavailability are potential causes.
  • Sender Reputation: Blacklisted IP addresses or a poor sender reputation can lead to rejections by Office 365 servers.
  • Authentication: Incorrect SPF or DKIM records can cause authentication failures and result in the 501 error.
  • Network Settings: Local firewalls, antivirus software, and MTU size restrictions can interfere with SMTP connections.
  • TLS Version: Outdated TLS versions on the sending server might not be supported by Office 365.

Key considerations

  • Validate Email Addresses: Always validate email addresses for correct syntax and avoid copying/pasting errors.
  • Check DNS Records: Ensure that your domain has valid MX records and that your sending server has a proper PTR record.
  • Monitor Sender Reputation: Regularly check your IP address against blacklists and maintain a good sender reputation.
  • Configure Authentication: Implement and correctly configure SPF and DKIM records to authenticate your emails.
  • Review Network Settings: Check local firewalls, antivirus software, and MTU sizes for potential interference with SMTP connections.
  • Update TLS Version: Ensure that your sending server supports TLS 1.2 or later for secure communication.
  • Test Connectivity: Use telnet to manually test SMTP connectivity and identify the point of failure.
Marketer view

Email marketer from EmailMarketingTips Blog explains that Incorrect SPF or DKIM records can lead to receiving mail servers rejecting the email. Make sure your SPF record includes the sending server's IP address and that DKIM signatures are valid.

November 2023 - EmailMarketingTips Blog
Marketer view

Email marketer from Reddit shares that the sending server may not have a proper reverse DNS (PTR) record, or the hostname in the HELO/EHLO greeting doesn't match the IP address. Some receiving mail servers reject connections from servers without proper reverse DNS.

April 2024 - Reddit

What the experts say
5Expert opinions

The 501 5.5.4 Invalid domain name error when sending emails to Office 365 can be caused by various factors. The bounce message may not be directly from MSN but from a different part of the Hotmail/Outlook infrastructure. A domain might have DNS issues, causing rejection of emails to it. It could also be an internal Microsoft problem related to nameserver misconfiguration. In addition, incorrect syntax or invalid characters in the recipient's address, and missing or incorrect MX records are all potential causes.

Key opinions

  • Bounce Origin: Bounce messages might originate from a different infrastructure than initially expected.
  • DNS Problems: Domain DNS issues can cause rejections due to inability to verify the domain.
  • Microsoft Internal Issues: Internal Microsoft infrastructure problems might affect email delivery.
  • Invalid Address Syntax: Incorrect email address syntax can result in the 'Invalid domain name' error.
  • MX Record Issues: Missing or misconfigured MX records lead to failures in email delivery.

Key considerations

  • Investigate Bounce Origin: When troubleshooting, consider the specific infrastructure generating bounce messages.
  • Check DNS Health: Verify DNS settings and ensure proper domain resolution.
  • Consider Internal Issues: Be aware of the possibility of internal problems within the email provider's infrastructure.
  • Validate Email Addresses: Always validate email addresses to ensure correct syntax.
  • Confirm MX Records: Check that the recipient domain has correctly configured MX records.
Expert view

Expert from Spam Resource suggests that invalid characters or syntax within the recipient's email address are common causes for the '501 5.5.4 Invalid domain name' error. Ensuring that the address adheres to RFC standards, with no unescaped special characters or spaces, is essential.

October 2024 - Spam Resource
Expert view

Expert from Word to the Wise explains that issues can arise from a domain lacking a valid MX record or from DNS problems that cause lookup failures. Checking DNS settings with tools like `dig` can help diagnose and fix such problems.

April 2021 - Word to the Wise

What the documentation says
5Technical articles

The 501 5.5.4 Invalid domain name error when sending emails to Office 365 is primarily caused by syntax errors in the recipient's email address, deviations from email address syntax standards, and incorrect DNS configurations for the recipient domain. Specifically, the error can arise from invalid characters, incorrect formatting, typos, or misuse of quotes in the email address. Missing or misconfigured MX records in the recipient domain's DNS settings also contribute. Furthermore, exceeding the message size or recipient limits imposed by Microsoft Exchange Online may trigger this error. Ultimately, the 501 error indicates a syntax error in the parameters or arguments sent to the SMTP server.

Key findings

  • Syntax Error: Syntax errors in the recipient's email address, such as invalid characters or incorrect formatting, are a primary cause.
  • DNS Misconfiguration: Missing or misconfigured MX records in the recipient domain's DNS settings can lead to this error.
  • SMTP Command Error: The 501 error indicates a syntax error in the parameters or arguments of the SMTP command.
  • Exchange Online Limits: Exceeding message size or recipient limits in Microsoft Exchange Online can trigger this error.
  • RFC Violations: Deviations from email address syntax standards as outlined in RFC specifications can cause a 501 error.

Key considerations

  • Validate Address Syntax: Carefully validate the syntax of the recipient's email address for errors, invalid characters, and typos.
  • Check MX Records: Verify that the recipient domain has correctly configured MX records in its DNS settings.
  • Review SMTP Commands: Ensure that SMTP commands are correctly formatted and that parameters adhere to specifications.
  • Respect Exchange Limits: Stay within the message size and recipient limits imposed by Microsoft Exchange Online.
  • Adhere to RFC Standards: Adhere to email address syntax standards defined in RFC specifications to avoid syntax errors.
  • Diagnose with MXToolbox: Use tools like MXToolbox to diagnose DNS configuration issues.
Technical article

Documentation from MXToolbox explains that the recipient domain's DNS configuration might be incorrect or incomplete. Specifically, missing or misconfigured MX records can cause this error. Use tools like MXToolbox to diagnose DNS issues.

February 2023 - MXToolbox
Technical article

Documentation from Microsoft Docs explains that a 501 5.5.4 error typically indicates a syntax error in the recipient's email address. This can be due to invalid characters, incorrect formatting, or a typo in the domain name.

April 2021 - Microsoft Docs

Related resources
4Resources

MDaemon smtp error 501: Domain must resolve - Collaboration ...
MDaemon smtp error 501: Domain must resolve - Collaboration ...

I don’t know what I did wrong or right, but right now my MDaemon is showing error 501: Domain must resolve while trying to send emails. I can receive emails normally, but can’t send them. Everything was working fine this morning, but I must’ve ticked something while reviewing the security settings. Help. Any ideas?

Spiceworks Community
SMTP ERROR 501 5.5.4 Invalid domain name 7.11 - General ...
SMTP ERROR 501 5.5.4 Invalid domain name 7.11 - General ...

After updating suitecrm version 7.11.0 I wanted to ge google calendar working. I couldn’t authenticate it because I did not have it associated with a domain name. So I used a domain name I had kicking around. I updated the config files, everything seemed to work fine. I realised today that the email functionality completely stopped working. The error I am getting is below. Is there somewhere I need to configure PHP mailer to the IP address. It appears that the inbox is syncing fine, just not th...

SuiteCRM
SMTP Email Error 501 5.5.4 - How to Resolve [SOLVED]
SMTP Email Error 501 5.5.4 - How to Resolve [SOLVED]

Discover how to solve SMTP Email Error 501 5.5.4 with our comprehensive guide. Learn about causes, detailed solutions for Gmail, Outlook, and Yahoo

Warmy Blog
Replies to Tickets no longer possible after port change from 443 to ...
Replies to Tickets no longer possible after port change from 443 to ...

Infos: Used Zammad version: 5.4.1 Used Zammad installation type: installation package Operating system: Ubuntu 18.04 LTS Browser + version: 8443 (SSL) Expected behavior: Replying to tickets should work despite port changeover Actual behavior: As soon as we change the port from 443 to 8443 and try to send a reply in a ticket, we get the following error message: Channel: Microsoft365::Account out Can’t use Channel::Driver::Smtp: #<Net::SMTPSyntaxError: 501 5.5.4 Invalid domain name [BE1P281CA...

Zammad - Community

Related questions