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What causes email delivery issues with Microsoft Outlook and are there deferrals from US/CA regions?

Summary

Email delivery to Microsoft Outlook, including Hotmail and other Microsoft domains, can be a complex challenge for senders. While sender reputation often plays a significant role in deliverability, there are instances where issues stem from internal technical difficulties within Microsoft's infrastructure. These can manifest as temporary deferrals, rather than outright rejections, and may affect specific geographic regions like the US and Canada.

What email marketers say

Email marketers often face a unique set of challenges when it comes to Microsoft Outlook deliverability. Beyond the usual concerns of sender reputation and content, they frequently encounter periods of unexplained deferrals or delays that appear to be system-wide rather than specific to their sending practices. The frustration is often compounded by difficulties in obtaining clear communication or rapid resolution from Microsoft's support channels.

Marketer view

An Email Geeks Marketer reported receiving an unprecedented message from Microsoft support, stating they were experiencing technical difficulties and engineers were working on a resolution. This was the first time they had seen such an explicit acknowledgment of internal issues from Microsoft.

19 Sep 2023 - Email Geeks

Marketer view

An Email Geeks Marketer noted that they were not alone in experiencing problems with Microsoft on a specific day, confirming a broader issue among senders rather than an isolated incident with their own mail flow.

19 Sep 2023 - Email Geeks

What the experts say

Email deliverability experts often approach Microsoft Outlook issues with a nuanced perspective, recognizing that the challenges extend beyond typical sender reputation management. They emphasize the interplay of technical infrastructure, sophisticated spam filtering algorithms, and Microsoft's dynamic policies. Understanding these deeper layers is crucial for diagnosing and mitigating delivery problems, especially when they stem from Microsoft's internal systems rather than sender misconfigurations or blocklist entries.

Expert view

A Deliverability Consultant from Word to the Wise explains that Microsoft's filters are highly dynamic and can react swiftly to anomalies in sending patterns. This often leads to unexpected deferrals or soft bounces, even for senders with generally good reputations, making consistent monitoring essential.

01 Nov 2023 - Word to the Wise

Expert view

A Spam Prevention Expert from SpamResource emphasizes the critical role of consistent email engagement metrics in maintaining a positive standing with Microsoft. They advise that strong open and click rates can help mitigate the impact of temporary system fluctuations or minor reputation dips.

10 Nov 2023 - SpamResource

What the documentation says

Official documentation from Microsoft and related security entities provides foundational guidance for email deliverability. While it doesn't typically detail real-time outage information, it outlines the best practices, technical requirements, and sender policies necessary to ensure emails reach Outlook.com inboxes. This includes adherence to authentication standards, volume management, and list hygiene, all critical factors even when technical difficulties temporarily impact delivery.

Technical article

Microsoft documentation on Delivery Status Notifications (DSN) clarifies that a 4.4.4 DSN code typically indicates a temporary routing error or an underlying network issue. This means the server was unable to route the message to the next hop for a transient reason, implying it should be retried later.

01 Oct 2023 - Microsoft Learn

Technical article

Office 365 Exchange Online documentation specifies that mail flow rules and anti-spam policies can impose throttling limits or defer messages based on various criteria. These include sender reputation, volume, and detected suspicious patterns, even for legitimate mail streams.

10 Oct 2023 - Exchange Online Documentation

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