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Why are we getting DNS resolution failures with outlook.com when sending email?

Summary

DNS resolution failures, particularly when sending emails to Outlook.com, can be a complex issue stemming from several interconnected factors. While it might initially appear to be a problem with the recipient's DNS, deeper investigation often reveals nuances in how DNS queries are handled by the sending infrastructure, especially regarding large response sizes and truncation. This situation is further complicated by inconsistencies in how some authoritative DNS servers (like Microsoft's) deliver DNS records.

What email marketers say

Email marketers and senders frequently encounter mysterious DNS resolution failures when targeting Outlook.com addresses. These issues often manifest as intermittent bounces, making them particularly challenging to diagnose. Marketers report seeing varying degrees of success and failure even within short timeframes, suggesting a transient or localized problem rather than a permanent misconfiguration.

Marketer view

Marketer from Email Geeks notes intermittent DNS failures for outlook.com, where the MX hostname resolves but the IP address does not. This leads to bounces even though the domain's MX records appear correct at first glance.

31 Jul 2023 - Email Geeks

Marketer view

Marketer from Spiceworks Community observes SPF TXT record issues with multiple DNS lookups, causing failures in Microsoft 365, indicating that SPF records exceeding lookup limits can trigger delivery problems.

10 Aug 2023 - Spiceworks Community

What the experts say

Email deliverability experts provide critical insights into the underlying technical reasons for DNS resolution failures with Outlook.com. Their analysis often focuses on the intricacies of DNS delegation, response truncation, and how various components in the mail flow (from authoritative DNS to MTAs) interact with DNS queries. These failures are often not simple misconfigurations but rather complex interactions that require detailed packet-level analysis.

Expert view

Expert from Email Geeks explains that the `+short` option hides crucial details in DNS query outputs, advising against its use for delegation diagnostics. Instead, viewing the AUTHORITY SECTION is vital for proper troubleshooting.

31 Jul 2023 - Email Geeks

Expert view

Expert from Spam Resource suggests that intermittent DNS resolution issues often indicate a problem further up the DNS chain. They highlight the need for persistent logging to capture the exact state during a failure.

15 Apr 2024 - Spam Resource

What the documentation says

Official documentation and technical guides provide foundational knowledge about DNS behavior and email authentication protocols crucial for understanding and mitigating resolution failures. They outline best practices, common pitfalls, and requirements set by major email providers like Microsoft. Adhering to these guidelines is essential for maintaining optimal email deliverability and avoiding blocklists or blocklist issues (sometimes known as blacklists).

Technical article

Documentation from Microsoft Tech Community warns that if you exceed 10 DNS lookups in your SPF record, your SPF check might fail, suggesting the use of tools to 'flatten' your record or reduce the number of includes to comply.

22 Mar 2024 - techcommunity.microsoft.com

Technical article

Documentation from DNS Made Easy stresses the importance of verifying that reverse DNS has been correctly set up for the IP address associated with your mail server to resolve email delivery issues.

22 May 2024 - dnsmadeeasy.com

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