Suped

Why is Microsoft Defender blocking emails on CTA clicks even if domains are not on DNS blacklists?

Summary

Microsoft Defender for Office 365 frequently blocks emails upon CTA clicks not due to traditional DNS blacklists, but because of its advanced, multi-layered threat protection. The core mechanism, Safe Links, conducts real-time URL scans when a user clicks, dynamically assessing the link's reputation and content. This dynamic analysis allows Defender to identify evolving threats like phishing, compromised legitimate sites, or suspicious behavioral patterns that static blacklists might miss. Additional protective measures include sophisticated anti-phishing policies, granular URL reputation scoring, and the ability to retroactively block links if their destination becomes malicious after initial email delivery.

Key findings

  • Real-Time Click Protection: Defender's Safe Links feature dynamically scans URLs at the moment of click, assessing their safety in real-time, independent of static DNS blacklists.
  • Behavioral and Heuristic Analysis: It employs advanced behavioral analysis and heuristic scanning to detect suspicious characteristics, such as unusual redirects, dynamic content, or attempts to download malicious files.
  • Anti-Phishing and Impersonation Defense: Policies are in place to detect and block links associated with phishing, brand impersonation, or user impersonation, even if the domain is otherwise valid.
  • Sophisticated Reputation Scoring: Defender uses a granular URL reputation system that factors in domain age, IP history, and content, providing a more nuanced assessment than simple blacklisting.
  • Dynamic Threat Identification: New or evolving threats, including zero-day attacks and compromised legitimate domains, are identified through dynamic analysis and sandboxing, bypassing traditional blacklist limitations.
  • Post-Delivery Remediation: Features like Zero-hour Auto Purge (ZAP) enable Defender to retroactively block access to URLs if their content or threat intelligence status changes after the email has been delivered.

Key considerations

  • Impact of Shared Tracking Domains: The use of shared click tracking domains can lead to blocks if other users of that domain engage in malicious activities, as the reputation is collectively assessed.
  • Potential for Over-Blocking: Defender's proactive and highly sensitive analysis may sometimes block legitimate URLs that exhibit characteristics similar to those used in phishing or malware campaigns.
  • Complex Redirects: Emails utilizing double redirects or multiple layered tracking systems may trigger Defender's blocking mechanisms due to their inherent suspicious nature.
  • Vendor Collaboration: When faced with persistent blocking issues related to click tracking, consulting the email service provider's support team is often necessary to investigate and resolve shared reputation concerns.
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What email marketers say

9 marketer opinions

Microsoft Defender for Office 365 (MDO) often blocks email links at the point of a call to action click, even when the associated domains are not present on traditional DNS blacklists. This robust protection goes far beyond static lists, leveraging real-time, dynamic analysis through features like Safe Links. MDO continuously evaluates the destination URL for sophisticated threats, including phishing attempts, malware distribution, and compromised legitimate websites that might not yet be widely known as malicious. Its advanced algorithms analyze URL behavior, content characteristics, and potential impersonation attempts, leading to proactive blocking based on evolving threat patterns and even post-delivery changes to link content. While effective against complex threats, this highly sensitive approach can sometimes result in the blocking of legitimate URLs that exhibit characteristics similar to those of malicious content.

Key opinions

  • Real-time Content & Behavior Scan: Microsoft Defender scrutinizes the live content and interactive behavior of linked pages at the moment of click, identifying threats like phishing pages, malware downloads, or unusual redirects regardless of the domain's blacklist status.
  • Granular URL Reputation: Beyond simple blacklists, Defender assesses a URL's reputation based on factors such as domain age, hosting IP history, and associated email campaign patterns.
  • Proactive Heuristic Blocking: Links can be blocked due to 'suspicious' characteristics on the landing page, like dynamic content or elements commonly associated with phishing, even if the content is benign, due to Defender's cautious algorithms.
  • Post-Delivery Threat Remediation: Features like Zero-hour Auto Purge (ZAP) allow Defender to retroactively block access to links if the content or threat intelligence changes to malicious after the email has been delivered.
  • Impersonation and Brand Spoofing Defense: Defender actively blocks links associated with attempts to impersonate trusted users, companies, or brands, preventing credential theft and brand abuse.

Key considerations

  • Minimizing Complex Tracking: To reduce block risks, email marketers should streamline tracking systems, avoiding excessive or double redirects that can appear suspicious to Defender's algorithms.
  • Addressing False Positives: Marketers may encounter situations where legitimate URLs are blocked; understanding Defender's heuristic analysis helps in troubleshooting these instances, as blocks can occur due to characteristics resembling threats rather than explicit malicious intent.
  • Maintaining URL and Domain Health: A proactive approach to URL reputation is vital, involving not just blacklist checks but also monitoring domain age, IP history, and avoiding content or associated campaigns that could degrade a link's overall standing.

Marketer view

Email marketer from Email Geeks shares that Microsoft Defender often blocks emails that use double redirects or have multiple tracking systems layered on top of each other.

4 Feb 2022 - Email Geeks

Marketer view

Marketer from Mimecast Blog explains that Microsoft Defender for Office 365 employs multiple layers of security beyond simple DNS blacklisting. When a user clicks a CTA, Defender's Safe Links feature performs a real-time reputation check and content analysis of the destination URL. This means a link can be blocked if the content behind it is deemed malicious, even if the domain is not explicitly blacklisted, because Defender is looking for more sophisticated threats like phishing pages, malware downloads, or compromised legitimate sites that haven't yet made it onto traditional blacklists.

26 Mar 2024 - Mimecast Blog

What the experts say

3 expert opinions

Microsoft Defender's email blocking on call-to-action clicks, even for domains not on traditional DNS blacklists, is primarily driven by its advanced Safe Links feature. This technology performs real-time URL scanning directly at the point of click, conducting dynamic reputation analysis to assess for threats. This goes beyond static list checks, offering an immediate defense against evolving malicious content. A common, often overlooked reason for legitimate links being blocked involves shared click tracking domains; if a domain used by multiple senders for link tracking is leveraged by others for scam or malicious activities, its overall reputation can decline, leading to blocks for all users, regardless of individual sender intent.

Key opinions

  • Real-time Click-Time Scans: Microsoft Defender's Safe Links feature inspects URLs precisely when a user clicks, bypassing static, pre-delivery assessments and traditional DNS blacklists.
  • Dynamic URL Reputation: Link blocking is based on an immediate, dynamic analysis of the URL's current reputation and content at the moment of click, rather than its presence on static blacklists.
  • Shared Domain Risk: A significant cause of legitimate blocks is the use of shared click tracking domains that have been leveraged by others for malicious or scamming purposes, tarnishing the collective domain reputation.
  • Independent of DNSBLs: The blocking mechanism operates independently of standard DNS blacklists, offering an additional, active layer of protection against evolving threats.

Key considerations

  • Vendor Communication for Tracking Domains: If shared click tracking domains are involved, direct consultation with the email service provider or vendor is advised to resolve reputation issues caused by other users' malicious activity.
  • Beyond Static Blacklists: Recognize that Microsoft Defender's blocking mechanism goes beyond static DNS blacklists, making real-time URL analysis a primary factor in deliverability.
  • Dynamic Reputation Impact: Understand that the reputation of your links, especially those using shared tracking domains, is subject to dynamic, continuous assessment by Microsoft Defender, independent of initial domain blacklisting.

Expert view

Expert from Email Geeks explains that the MS Defender blocks occurring upon clicking CTAs are likely due to a shared click tracking domain being used by others, possibly for scam websites, resulting in a legitimate block. She clarifies that this is not a DNSBL issue and advises contacting the vendor.

25 Nov 2021 - Email Geeks

Expert view

Expert from Spam Resource explains that Microsoft Defender's Safe Links feature actively scans URLs in emails at the time a user clicks them. Even if a domain is not on a DNS blacklist, the link can be blocked if it's determined to be malicious at the click-time, based on dynamic reputation analysis. This real-time scanning provides an additional layer of protection beyond traditional static blacklists.

4 Jul 2022 - Spam Resource

What the documentation says

4 technical articles

Microsoft Defender for Office 365 blocks emails at the point of a call-to-action click, even when domains are not on DNS blacklists, by employing a sophisticated, multi-faceted threat detection system. Its Safe Links feature performs real-time URL scanning when a user clicks, dynamically assessing the link's safety. This goes beyond static blacklist checks to identify emerging threats like new phishing sites or compromised legitimate domains. Furthermore, Defender uses principles from Safe Attachments, such as sandboxing and behavioral monitoring, to detonate URLs in virtual environments, detecting zero-day and cloaked threats. Comprehensive Anti-Phishing policies also analyze overall email context, sender reputation, and URL characteristics to block links associated with impersonation or phishing schemes, prioritizing user safety over traditional domain reputation.

Key findings

  • Click-Time Real-time Scanning: Safe Links conducts dynamic URL inspections at the moment of a user's click, providing immediate protection independent of static DNS blacklists.
  • Advanced Behavioral Analysis: Utilizing techniques similar to Safe Attachments, Defender detonates URLs in virtual environments to detect unknown malware, zero-day exploits, and suspicious behavioral patterns.
  • Contextual Phishing Detection: Anti-Phishing policies analyze various email indicators, including sender and content, to block links associated with brand or user impersonation, even if the linked domain appears legitimate.
  • Evolving Threat Combat: Defender continuously adapts its capabilities to combat sophisticated phishing attacks, including those employing domain or display name spoofing and look-alike domains with otherwise 'clean' URLs.

Key considerations

  • Beyond Static Blacklists: Marketers should understand that Defender's blocking decisions are based on dynamic, real-time threat analysis and comprehensive contextual evaluation, not solely on traditional DNS blacklists.
  • Proactive Blocking of Subtle Threats: The system's ability to detect suspicious behavior, impersonation attempts, and cloaked threats means legitimate URLs can be blocked if they exhibit characteristics that align with sophisticated attack vectors.
  • Multi-Layered Protection: Deliverability efforts must account for Defender's combined use of Safe Links, Safe Attachments principles, and Anti-Phishing policies, which collectively assess URLs for a wide range of threats.

Technical article

Documentation from Microsoft Learn explains that Microsoft Defender for Office 365's Safe Links feature provides URL protection at the time of click. Instead of relying solely on DNS blacklists, Safe Links rewrites URLs in incoming emails and scans them in real-time when a user clicks. If a rewritten URL is determined to be malicious or suspicious during this click-time scan, the user is blocked from accessing the site, regardless of the domain's presence on a static DNS blacklist. This dynamic analysis identifies threats that traditional blacklists might miss, such as newly created phishing sites or legitimate domains compromised to host malicious content.

7 Dec 2021 - Microsoft Learn

Technical article

Documentation from Microsoft Learn explains that beyond Safe Links, Microsoft Defender for Office 365 utilizes Safe Attachments, which applies sandboxing technology to detect unknown malware and viruses. While primarily for attachments, the underlying dynamic analysis and behavioral monitoring principles extend to URL evaluations. This means that even if a domain isn't blacklisted, Defender's advanced threat protection can identify and block links that lead to content exhibiting suspicious behavior, even if the threat is zero-day or cloaked, by detonating the URL in a virtual environment.

31 Mar 2023 - Microsoft Learn

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