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How can I improve email deliverability with Microsoft and avoid spam filters?

Summary

Improving email deliverability to Microsoft domains like Outlook and Hotmail often presents unique challenges for senders. These challenges range from initial warmup difficulties to persistent filtering into the spam folder, even for legitimate mail. Microsoft's filtering systems are known for their complexity and, at times, their lack of transparent feedback, leading to frustration among email marketers and deliverability professionals. Effectively navigating these systems requires a combination of strong technical setup, consistent sender practices, and persistent engagement with Microsoft's support channels when issues arise. Understanding why your emails face deliverability issues with Microsoft is the first step towards resolving them.

What email marketers say

Email marketers frequently express frustration over Microsoft's unpredictable and often challenging email filtering. Many report experiencing anxiety and stress due to emails being sent to the spam or junk folder, even when following standard best practices like slow warmups. There's a shared sentiment that Microsoft operates somewhat independently from the broader email community, making direct communication and issue resolution difficult. Despite these challenges, marketers emphasize the importance of persistence and a strong technical foundation to gradually improve inbox placement.

Marketer view

Marketer from Email Geeks observes that despite their confidence and experience in email deliverability, Microsoft has become almost impossible to deal with lately, causing significant anxiety and stress, especially concerning warmups.

20 Jul 2022 - Email Geeks

Marketer view

Marketer from Email Geeks suggests that if you are confident your client is a good sender, just keep replying to tickets and filing new ones when they stop responding, as this seems to be the only eventual route to success, noting it can be nearly impossible in shared IP spaces.

20 Jul 2022 - Email Geeks

What the experts say

Experts in email deliverability acknowledge the unique complexities of sending to Microsoft domains. They recognize that Microsoft's filtering can be less transparent and less responsive to senders compared to other major Mailbox Providers (MBPs). While some perceive Microsoft as a challenge designed to hone a deliverability professional's skills, there's a general consensus that rigorous adherence to technical standards and persistent communication, even if difficult, is necessary. The emphasis is often on ensuring fundamental email authentication protocols are flawlessly implemented, as these form the bedrock of trust with Microsoft's systems.

Expert view

Expert from Email Geeks suggests that Mailbox Providers (MBPs) face many challenges, subtly hinting that Microsoft's specific difficulties are part of a broader landscape but perhaps handled differently by Microsoft.

20 Jul 2022 - Email Geeks

Expert view

Expert from Email Geeks notes that while Mailbox Providers face challenges, some actively participate in the community of nations and are more willing to communicate directly with senders, implying Microsoft is an outlier.

20 Jul 2022 - Email Geeks

What the documentation says

Official documentation and technical guides from Microsoft and other authoritative sources provide critical insights into how Microsoft's email filtering systems operate. They emphasize the importance of adhering to industry standards for email authentication (SPF, DKIM, DMARC), maintaining sender reputation, and understanding specific guidelines related to content and sending practices. While the documentation may not always address every nuanced deliverability issue, it forms the foundational knowledge necessary to optimize email programs for Microsoft domains and avoid common pitfalls that lead to emails being blocklisted or sent to the junk folder.

Technical article

Microsoft documentation highlights that Microsoft 365 email spam filtering works by comparing incoming mail against IP blocklists of known spam sources and by using proprietary machine learning models to identify and block malicious or unwanted emails.

15 Dec 2023 - SpamTitan Email Security

Technical article

Official guidelines emphasize that senders should avoid using shortened or broken URLs within their email content, and too many Call-to-Action (CTA) buttons, as these can negatively impact Microsoft's content associated scores.

20 Feb 2024 - Blueshift

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