HomeAI ToolsEmail Security
Buyer Guide 2026

Best AI Email Security Tools

We evaluated Proofpoint, Mimecast, Microsoft Defender for Office 365, Abnormal Security, Avanan/Check Point, and Cofense on AI detection accuracy, BEC protection, deployment complexity, and total cost. Six verdicts for security teams choosing their email security platform.

Platform Verdicts

Honest assessments of when each email security platform delivers value and when alternatives are worth considering.

Proofpoint Email Security

✓ Ship It

Best enterprise email security for organizations prioritizing threat intelligence depth and BEC protection — unmatched threat data from 7.5 billion messages analyzed daily

Proofpoint Email Security is the enterprise market leader in email threat protection, providing multi-layer defense against phishing, BEC (business email compromise), malware, ransomware, and impostor threats through a combination of static analysis, behavioral sandboxing (TAP — Targeted Attack Protection), URL rewriting, and ML-based impostor detection that analyzes sender behavior rather than just message content. Proofpoint's competitive advantage is threat intelligence scale: with 7.5 billion messages analyzed daily across 230,000+ enterprise customers, Proofpoint's Nexus Threat Intelligence platform trains ML models on more email threat data than any other vendor — which is why Proofpoint consistently achieves industry-leading phishing catch rates in third-party assessments. Proofpoint's AI capabilities include Nexus AI for behavioral sender analysis that detects BEC attempts by modeling normal supplier and executive communication patterns and flagging deviations; TAP sandboxing that uses ML to analyze malicious file behaviors in isolated environments; and Proofpoint Targeted Attack Protection (URL Defense) that rewrites URLs and evaluates destination pages at click-time to block newly malicious pages that were benign at delivery time.

Ship Signal

Nexus Threat Intelligence scale is unmatched — Proofpoint's position as the highest-volume email security gateway gives its ML models training data advantages that smaller vendors cannot replicate; 7.5 billion daily messages means new phishing campaigns, BEC techniques, and malware delivery patterns are identified minutes after they appear in the wild on Proofpoint-protected organizations and converted to detection signatures before they reach the next target. BEC detection accuracy is the market reference standard — Proofpoint's ML models for impersonation and BEC attempt detection (Very Attacked People targeting, supplier impostor detection, executive impersonation) consistently achieve the lowest false negative rates in Gartner and Forrester assessments; for organizations in financial services, legal, and healthcare where a single successful BEC attack can cost $1M+, Proofpoint's accuracy premium over lower-cost alternatives is straightforward to justify. People-centric security extends beyond gateway to user behavior — Proofpoint Security Awareness Training integrates with threat detection to automatically enroll users who interact with real phishing emails in targeted training, creating a feedback loop between attack data and security awareness that generic phishing simulation platforms cannot achieve because they use simulated rather than real attack data.

Skip Signal

Pricing is the market's highest for enterprise deployments — Proofpoint's pricing reflects its position as the market leader; enterprise bundles (Email Protection + TAP + Security Awareness) are priced significantly above Microsoft's bundled Defender for Office 365, which is included in Microsoft 365 E3/E5 subscriptions; organizations already paying for Microsoft 365 E5 should rigorously evaluate whether the Proofpoint incremental detection value justifies the significant additional investment. Microsoft 365 + Proofpoint integration creates connector configuration complexity — deploying Proofpoint as a gateway in front of Microsoft 365 requires MX record changes, smart host configuration, and connector management that introduces additional operational overhead compared to native Microsoft Defender for Office 365 deployment; misconfigurations in the gateway architecture can cause mail delivery issues that require Proofpoint expertise to diagnose. Security Awareness Training is a separate product with additional licensing — Proofpoint's phishing simulation and security awareness capabilities require additional licensing beyond the email security gateway; organizations that want integrated threat + training capabilities must budget for both modules.

AI Features:

  • Nexus AI ML behavioral analysis for BEC and impostor detection
  • TAP (Targeted Attack Protection) AI sandboxing for zero-day malware analysis
  • Click-time URL evaluation for newly malicious page detection at click
  • Very Attacked People identification and targeted protection prioritization
  • AI-powered supplier impostor detection from communication graph analysis
  • Nexus Threat Intelligence training on 7.5 billion daily messages
Best for: Large enterprises prioritizing maximum email threat detection accuracy, BEC protection, and integrated security awareness training — particularly financial services, legal, and healthcare organizations where a single BEC success is catastrophic
Pricing: Annual subscription per user. Bundle pricing for Email Protection + TAP + Security Awareness Training. Contact for enterprise pricing — typically $10–20/user/month for complete bundle.

Mimecast

✓ Ship It

Best email security for Microsoft 365 environments needing integrated continuity, archiving, and threat protection — the only platform that combines security, continuity, and compliance in a single email security stack

Mimecast is a cloud-native email security platform that uniquely integrates threat protection, email continuity (maintaining email access during Microsoft 365 outages), archiving (with legal hold and eDiscovery capabilities), and security awareness training — providing a comprehensive email management platform rather than a point threat detection product. Mimecast's competitive differentiation from Proofpoint and Microsoft Defender is its continuity and archiving capabilities: Mimecast Continuity automatically routes email delivery through Mimecast's cloud when Microsoft 365 experiences an outage, ensuring organizations maintain email access during the service disruptions that Microsoft's SLA acknowledges can occur; this is a unique capability that neither Proofpoint nor Microsoft Defender provides. Mimecast's AI capabilities include ML-based phishing detection that analyzes email content, sender behavior, and URL characteristics; impersonation protection that detects executive and domain impersonation attempts; and Mimecast's targeted threat protection that rewrites URLs and sandboxes attachments to catch zero-day malware delivery.

Ship Signal

Email continuity is a unique differentiator no other email security vendor provides — Mimecast's continuity service maintains email access through a purpose-built backup email platform when Microsoft 365 experiences outages; Microsoft's own SLA acknowledges service degradation events occur, and Mimecast's continuity service ensures organizations can continue email operations during these windows rather than experiencing complete email outage; this capability is increasingly valued by organizations that have experienced high-profile Microsoft 365 outages affecting business operations. Integrated archiving eliminates separate compliance tool investment — Mimecast's archiving with legal hold, eDiscovery search, and retention policy management is built into the same platform as threat protection, eliminating the separate archiving investment (Veeam, AvePoint, native Microsoft) that organizations without Mimecast must make; for organizations with significant eDiscovery activity or long retention requirements (7+ years), the integrated archiving value is significant. Competitive pricing for the integrated bundle — Mimecast's threat protection + continuity + archiving bundle is priced comparably to Proofpoint's threat-protection-only bundle, making the integrated value proposition straightforward; organizations paying separately for email security and email archiving consistently find Mimecast's bundle more cost-effective.

Skip Signal

BEC and impersonation detection accuracy trails Proofpoint — Mimecast's ML-based impersonation detection is capable but has historically been scored below Proofpoint's Nexus AI in third-party BEC detection assessments; organizations where BEC protection accuracy is the primary selection criterion should carefully evaluate current Mimecast BEC detection performance against Proofpoint and Abnormal Security before selecting Mimecast. Mimecast ownership transition creates uncertainty — Mimecast was acquired by Permira (private equity) in 2021; while the product has continued to develop, PE ownership sometimes leads to cost-cutting or strategic pivots that affect product investment; organizations evaluating multi-year commitments should assess Mimecast's ownership context. Continuity value requires Microsoft 365 — Mimecast's continuity feature is valuable specifically for Microsoft 365 environments; organizations not on Microsoft 365 (Google Workspace, self-hosted Exchange) lose the primary differentiating value and should evaluate Proofpoint or Abnormal instead.

AI Features:

  • ML-based phishing detection analyzing content, sender behavior, and URL patterns
  • AI impersonation protection for executive and domain spoofing detection
  • Targeted Threat Protection URL rewriting and sandbox analysis
  • Behavioral AI for internal email anomaly detection
  • AI-powered archiving categorization and eDiscovery relevance scoring
  • Security awareness training ML personalization based on individual user risk profiles
Best for: Microsoft 365 organizations needing integrated threat protection + email continuity + archiving in a single platform — most valuable for organizations that require email availability guarantees during Microsoft 365 outages and have compliance archiving requirements
Pricing: Annual subscription per user. Pricing varies by bundle (Threat Protection, Continuity, Archiving, Security Awareness). Contact for enterprise quote — typically $8–15/user/month for full bundle.

Microsoft Defender for Office 365

✓ Ship It

Best value email security for Microsoft 365 E3/E5 customers — native integration eliminates gateway complexity, and Plan 2 AI capabilities have improved dramatically to approach Proofpoint-level detection

Microsoft Defender for Office 365 (formerly Advanced Threat Protection / ATP) is Microsoft's native email security platform for Microsoft 365 environments, providing anti-phishing, Safe Links (URL rewriting and click-time evaluation), Safe Attachments (sandboxing for malicious files), anti-BEC (user impersonation and domain spoofing protection), and Defender XDR integration that correlates email threats with endpoint, identity, and cloud security signals in a unified security operations console. Microsoft Defender for Office 365 Plan 2 (included in Microsoft 365 E5 or available as an add-on to E3) extends Plan 1 capabilities with Attack Simulator, Threat Explorer for threat hunting, Priority Account Protection (enhanced protections for executives and high-value targets), and full Defender XDR integration. Microsoft's AI capabilities in email security have improved significantly: Microsoft's security research team has applied large language model capabilities to phishing detection (analyzing email writing style and context), and Defender's integration with Microsoft's global threat intelligence (trillions of signals daily across Azure, Microsoft 365, and Windows endpoint telemetry) provides threat detection breadth that specialized email security vendors cannot match through email-only intelligence.

Ship Signal

Zero incremental cost for Microsoft 365 E5 customers — Microsoft Defender for Office 365 Plan 1 is included in Microsoft 365 Business Premium, E3, and higher; Plan 2 is included in E5; organizations already paying for Microsoft 365 E5 receive enterprise-grade email security at no additional cost, which completely changes the ROI calculation compared to running a separate Proofpoint or Mimecast deployment that costs $10–20/user/month on top of Microsoft 365 licensing. Native integration with Defender XDR creates unified threat investigation — when a phishing email is detected in Defender for Office 365, the same Defender XDR console shows whether the malicious link was clicked, whether the endpoint clicked on a managed device, whether credentials were compromised, and what post-compromise activity occurred; this cross-domain correlation is impossible with gateway-based email security products that cannot see endpoint behavior. Priority Account Protection is uniquely tailored to high-value targets — Microsoft's Priority Account feature provides enhanced email scrutiny, dedicated attack monitoring, and SOC alert prioritization for executives and high-value accounts (CFOs, board members, legal team) that are specifically targeted by BEC campaigns; the prioritization is applied automatically based on the account designation without requiring separate policy configuration.

Skip Signal

Detection accuracy still trails Proofpoint and Abnormal for sophisticated BEC attacks — despite significant AI investment, independent assessments continue to show Microsoft Defender for Office 365 with lower catch rates for sophisticated BEC and social engineering attacks compared to Proofpoint and Abnormal Security; organizations in industries with high BEC risk (financial services, legal, M&A advisors) may find the incremental detection from adding Proofpoint or Abnormal Security on top of Defender justified even accounting for the additional cost. Configuration complexity in Microsoft 365 admin center — Defender for Office 365 policy configuration is distributed across the Microsoft 365 Defender portal, Exchange admin center, and Microsoft Entra ID; organizations transitioning from third-party email security gateways report the distributed policy management creates confusion and misconfiguration risk. Plan 1 vs. Plan 2 capability gap — Microsoft 365 E3 includes only Plan 1 (Safe Links, Safe Attachments, anti-phishing) without the advanced capabilities (Attack Simulator, Threat Explorer, Priority Account Protection, full XDR integration) available in Plan 2 (E5); organizations on E3 receive meaningful but not complete Defender for Office 365 capability.

AI Features:

  • LLM-based phishing detection analyzing email writing style and contextual anomalies
  • Safe Links click-time URL evaluation against Microsoft's global threat intelligence
  • Safe Attachments AI sandboxing using detonation and behavioral analysis
  • Anti-BEC ML impersonation detection for executive and domain spoofing
  • Priority Account Protection enhanced AI scrutiny for high-value targets
  • Attack Simulator AI-generated phishing simulations for security awareness training
Best for: Microsoft 365 E3/E5 customers where Defender for Office 365 is included in existing licensing — Plan 2 (E5) provides enterprise-grade capabilities; organizations with high BEC risk should evaluate adding Abnormal Security on top of Defender for incremental detection
Pricing: Included in Microsoft 365 Business Premium, E3 (Plan 1), and E5 (Plan 2). Add-on available for E1/E3. Microsoft 365 E5 from $57/user/month includes full Defender for Office 365 Plan 2.

Abnormal Security

✓ Ship It

Best AI-native email security for BEC and supply chain compromise detection — behavioral AI baseline catches attacks that signature-based and rule-based tools systematically miss

Abnormal Security is an API-based email security platform that uses behavioral AI to detect BEC, phishing, malware, and supply chain compromise attacks by building behavioral baselines for every user and vendor in the Microsoft 365 or Google Workspace environment — then detecting deviations from normal communication patterns that indicate compromised accounts, impersonation attempts, or social engineering attacks that traditional signature-based email security tools cannot catch because they have no malicious signature to match against. Abnormal's architecture is a fundamental departure from traditional email security: rather than acting as an MX-record-based gateway that intercepts and scans email before delivery (Proofpoint, Mimecast), Abnormal connects via native Microsoft 365 or Google Workspace API and analyzes email after delivery, providing a complementary detection layer that catches the attacks that gateway-based tools miss without adding latency to email delivery. Abnormal's AI model processes signals including sender identity patterns, communication frequency, language style analysis, attachment behavior, link patterns, and financial instruction context to detect the subtle behavioral anomalies that characterize sophisticated BEC, VEC (vendor email compromise), and credential phishing attacks.

Ship Signal

Behavioral baseline detects zero-signature BEC attacks that all other tools miss — Abnormal's model for detecting BEC does not require known-bad signatures, URL blocklists, or attachment reputation scores; it detects that a message claiming to be from the CFO asking the finance team to wire $450,000 deviates from the CFO's normal communication patterns (wrong device, unusual time, different vocabulary), which catches BEC attacks that have bypassed all conventional email security controls because they contain no detectable malicious content. API-based deployment augments existing email security without gateway changes — Abnormal deploys as an API integration with Microsoft 365 or Google Workspace rather than requiring MX record changes or mail flow architecture changes; organizations can add Abnormal to existing Proofpoint or Microsoft Defender deployments without disrupting email delivery configuration, which dramatically reduces deployment risk and allows security teams to measure Abnormal's incremental catch rate against existing tools. VEC (vendor email compromise) detection is unique in the market — Abnormal models communication patterns for the organization's entire vendor ecosystem (1,000+ suppliers for a typical enterprise) and detects compromised vendor accounts or impersonation attempts that exploit existing vendor relationships; VEC attacks that use legitimate-looking email addresses from actual vendor domains are the attack type most likely to succeed against gateway-based detection and most effectively caught by Abnormal's behavioral approach.

Skip Signal

API-based architecture means email is delivered before remediation — unlike gateway-based security that blocks email before delivery, Abnormal detects and remediates threats after they land in inboxes; while Abnormal achieves automatic remediation within seconds of detection, there is a brief window between delivery and remediation during which a user could interact with a malicious email; for organizations where any inbox delivery of malicious email is unacceptable, gateway-based security remains necessary. Pricing is additive to existing email security investment — Abnormal is designed as a complementary layer to Microsoft Defender for Office 365 or existing gateway-based security, not a replacement; organizations must budget for Abnormal in addition to existing email security licensing, which typically adds $3–5/user/month on top of existing costs. Limited standalone detection for non-BEC threats — Abnormal's strongest capabilities are in BEC, VEC, and credential phishing detection; for malware delivery, ransomware, and spam filtering, gateway-based tools like Proofpoint remain more capable; organizations replacing rather than augmenting their email security stack with Abnormal will have coverage gaps for traditional email threats.

AI Features:

  • Behavioral AI baseline for every user and vendor without signatures or rules
  • VEC (vendor email compromise) detection from supplier communication graph analysis
  • Language style analysis for detecting account compromise and social engineering
  • Automated email remediation within seconds of behavioral anomaly detection
  • Financial instruction context analysis for wire transfer and invoice fraud detection
  • AI-powered SOC workflow: pre-built investigation summaries for detected threats
Best for: Organizations seeking best-in-class BEC and VEC detection as a complementary layer to Microsoft Defender for Office 365 or an existing gateway — particularly effective for organizations that have already experienced BEC incidents despite conventional email security
Pricing: Annual subscription per mailbox. Typically $3–6/mailbox/month. Contact for enterprise pricing. API-based deployment requires Microsoft 365 or Google Workspace.

Avanan (Check Point)

✓ Ship It

Best API-based email security for organizations using multiple cloud collaboration platforms — extends beyond email to Microsoft Teams, Slack, SharePoint, and OneDrive in a single platform

Avanan (acquired by Check Point in 2021) is an API-based cloud email and collaboration security platform that uses Check Point ThreatCloud AI threat intelligence to detect phishing, malware, account takeover, and BEC threats across email (Microsoft 365 and Google Workspace) and cloud collaboration platforms (Microsoft Teams, Slack, SharePoint, OneDrive, Box, Dropbox) — providing a single security layer for the complete cloud collaboration stack rather than email-only protection. Avanan's differentiation from Abnormal Security is collaboration platform coverage: while Abnormal focuses on email-only behavioral detection, Avanan extends threat detection to the Microsoft Teams messages, SharePoint file shares, and OneDrive syncs that attackers increasingly use as malware delivery vectors after initial email compromise. Avanan's AI capabilities include Check Point ThreatCloud AI threat intelligence integration (the same threat intelligence that powers Check Point Quantum firewalls) for real-time phishing URL and malware hash reputation, ML-based phishing content analysis, and behavioral analytics for account takeover detection.

Ship Signal

Multi-platform coverage extends security beyond email to Teams and SharePoint — attackers increasingly deliver malware through Microsoft Teams messages and SharePoint file links after initial email compromise, because users trust file shares from internal Teams conversations more than email attachments; Avanan's coverage of Teams, SharePoint, and OneDrive fills the security gap that email-only tools (Proofpoint, Mimecast, Abnormal) cannot address. ThreatCloud AI integration provides real-time threat intelligence — Avanan's integration with Check Point ThreatCloud AI (the same threat intelligence platform used by 150,000+ Check Point-protected networks) provides phishing URL detection and malware reputation data at a scale that independent email security vendors cannot match; threat actors using infrastructure associated with known campaigns are blocked immediately when ThreatCloud updates. API-based deployment without MX record changes enables rapid value — like Abnormal, Avanan deploys via API without requiring MX record or mail flow changes, enabling deployment in hours; organizations that need rapid coverage improvement without mail flow architecture changes find API-based tools significantly faster to implement than gateway alternatives.

Skip Signal

BEC behavioral detection depth trails Abnormal — Avanan's threat detection relies more heavily on signature-based and reputation-based detection from ThreatCloud than behavioral baseline analysis; for detecting novel BEC attacks with no malicious signatures, Abnormal's pure behavioral approach consistently outperforms ThreatCloud-reputation-dependent detection. Check Point acquisition integration maturity requires validation — Avanan was acquired in 2021 and has been integrated into the Check Point product portfolio, but the integration between Avanan's API-based architecture and Check Point's broader security platform (SmartConsole, Harmony) is still maturing; organizations should validate current integration capabilities rather than assuming seamless Check Point ecosystem integration. Pricing transparency is limited — Avanan's pricing is not publicly published and requires direct engagement; organizations comparing Avanan to Abnormal, Mimecast, and Microsoft Defender should obtain explicit quotes for comparison.

AI Features:

  • Check Point ThreatCloud AI threat intelligence for real-time URL and file reputation
  • ML-based phishing content and social engineering detection
  • Behavioral analytics for Microsoft 365 and Google Workspace account takeover
  • AI-powered threat detection for Microsoft Teams and Slack messages
  • Automated remediation across email and collaboration platforms
  • Natural language processing for BEC and impostor attempt identification
Best for: Organizations using Microsoft 365 (Teams, SharePoint, OneDrive) or Google Workspace with Slack who need threat protection extending beyond email to collaboration platforms in a single API-based deployment
Pricing: Annual subscription per user. Contact Avanan/Check Point for current pricing — not publicly disclosed. Enterprise quotes typically available within 24 hours.

Cofense

✓ Ship It

Best phishing simulation and human-as-sensor platform — combines security awareness training with crowdsourced threat intelligence from 35+ million employees reporting phishing globally

Cofense (formerly PhishMe) is a phishing defense platform that combines security awareness training (simulated phishing campaigns), a one-click phishing reporting button (PhishMe Reporter), and a phishing threat intelligence network that processes reported phishing emails from 35+ million trained employees globally to generate real-time threat intelligence for automated email platform integrations. Cofense's unique positioning is the human-as-sensor model: rather than purely technical email security, Cofense trains employees to recognize and report phishing, then uses the crowdsourced reports to identify active phishing campaigns faster than automated technical detection — because human recipients recognize context-specific social engineering that automated systems miss. Cofense Vision provides automated inbox-level phishing remediation based on reported threats, searching all Microsoft 365 or Google Workspace mailboxes for email matching reported phishing indicators and removing them automatically without requiring security team members to manually remediate each instance.

Ship Signal

35+ million reporter network provides crowdsourced threat intelligence at unprecedented scale — Cofense's network of trained employees reporting real phishing emails generates threat intelligence on active campaigns hours before those campaigns appear in commercial threat feeds; when 1,000 employees at different organizations report the same phishing template within an hour, Cofense's platform identifies the campaign, extracts indicators, and distributes them to integrated email security platforms before the campaign targets additional organizations. Human-as-sensor model catches context-specific social engineering that automated tools miss — employees who have been trained on phishing recognition successfully identify targeted spear-phishing attacks that reference specific internal projects, colleague names, and business context that automated tools cannot evaluate for plausibility; the human element in phishing detection is uniquely capable of recognizing social engineering that exploits organizational context unavailable to external threat intelligence feeds. Automated remediation closes the window between phishing delivery and compromise — Cofense Vision's automated remediation removes phishing emails from all mailboxes within minutes of the first report, eliminating the scenario where a phishing email is reported by one employee but not yet removed from 50 other inboxes; this automation is critical for containing the exposure window when phishing campaigns target multiple employees simultaneously.

Skip Signal

Cofense is a phishing defense platform, not a complete email security solution — Cofense does not provide the full email security gateway capabilities (spam filtering, malware detection, BEC protection) that Proofpoint and Mimecast provide; organizations cannot replace their email security gateway with Cofense and should plan for it as a complementary security awareness and human-reporting layer. Security awareness training effectiveness is content-dependent — Cofense's phishing simulations are most effective when they use realistic scenarios that reflect the social engineering techniques current attackers use; organizations that do not regularly update their simulation content to reflect current threat actor tactics will find employee click rates on simulations diverging from click rates on real phishing. Reporting fatigue can reduce human sensor effectiveness — security teams that do not provide timely feedback to employees who report phishing (acknowledgment that the report was received and whether it was a real threat or a simulation) see reporting rates decline over time as employees conclude that reporting doesn't matter; Cofense's value as a human sensor depends on maintaining high reporting engagement.

AI Features:

  • AI-powered phishing simulation generation from current threat actor campaign templates
  • ML-based reported email triage for separating real threats from simulated tests
  • Automated phishing campaign identification from global reporter network patterns
  • Cofense Vision AI threat hunting across mailboxes for reported indicator matches
  • Risk-based employee vulnerability scoring from simulation click and report behavior
  • Natural language processing for phishing email content analysis and classification
Best for: Organizations that want to combine security awareness training with human-as-sensor phishing reporting and automated inbox remediation — most effective as a complementary layer to gateway-based email security
Pricing: Annual subscription per user. PhishMe training, Reporter, and Vision are separately licensed. Contact for bundled enterprise pricing — typically $2–5/user/month for complete platform.

Email Security Decision Matrix

Match your organization profile to the right email security platform.

Large enterprise, maximum detection accuracy, BEC is primary threat vectorProofpoint Email Security

Nexus AI trained on 7.5B daily messages; market-leading BEC detection accuracy; integrated security awareness training with real threat data

Microsoft 365 needing continuity, archiving, and threat protection in one platformMimecast

Only platform combining threat protection, email continuity during M365 outages, and archiving/eDiscovery at comparable pricing to threat-only alternatives

Microsoft 365 E5 customer maximizing included security valueMicrosoft Defender for Office 365 Plan 2

Included in E5 at no additional cost; native XDR integration across endpoint, identity, and email; LLM-based detection that has closed gap with specialist vendors

Add best-in-class BEC/VEC detection on top of existing email securityAbnormal Security

API-based deployment without MX changes; behavioral baseline catches zero-signature BEC that signature-based tools miss; strongest VEC (vendor email compromise) detection in market

Need security across email + Teams + SharePoint + Slack in one platformAvanan (Check Point)

Only platform extending AI threat detection beyond email to Microsoft Teams, SharePoint, OneDrive, and Slack collaboration — critical as attackers pivot to collaboration vectors

Build human-as-sensor phishing defense and security awareness programCofense

35M+ reporter network provides crowdsourced threat intelligence; automated remediation from reported phishing; most effective security awareness training tied to real threat data

Email Security Deployment Warnings

Critical configuration mistakes and program gaps that undermine email security effectiveness.

Microsoft Defender for Office 365 Safe Links and Safe Attachments must be configured — default state is not optimal

Deploying Microsoft Defender for Office 365 without customizing the default anti-phishing, Safe Links, and Safe Attachments policies leaves organizations with suboptimal protection. The default preset policies are a starting point, not a hardened configuration. Security teams should enable 'Defender for Office 365 Strict' protection presets for executive accounts, configure anti-phishing impersonation protection with key executive and domain names, and enable 'Apply real-time URL detonation' in Safe Links to maximize detection effectiveness.

Email gateway deployment in front of Microsoft 365 can interfere with Microsoft security signals

Deploying a gateway-based email security tool (Proofpoint, Mimecast) as the primary MX record means Microsoft 365 receives already-processed email rather than raw email — which can reduce Microsoft Defender for Office 365's threat signal quality and affect features that depend on analyzing original headers. Organizations running third-party gateways with Microsoft Defender should configure the gateway's IP addresses in Exchange connection filtering as allowed sources and validate that Defender's email authentication signals (SPF, DKIM, DMARC) function correctly with the gateway in the mail flow path.

Security awareness training without simulations based on current threat actor techniques provides false confidence

Generic phishing simulations that use obvious 'fake' scenarios (poorly formatted emails with suspicious domains) train employees to recognize the easiest phishing attempts while missing the sophisticated social engineering that causes actual breaches. Security awareness programs should include simulations that use current threat actor techniques: executive impersonation using look-alike domains, vendor email compromise scenarios referencing realistic supplier names, and business context-specific phishing that requires employees to recognize subtle anomalies rather than obvious malicious indicators.

BEC protection requires DMARC enforcement, not just DMARC monitoring

DMARC (Domain-based Message Authentication, Reporting & Conformance) in monitoring mode (p=none) collects data about your domain's email authentication status but does not block impersonation. Moving to DMARC enforcement (p=quarantine or p=reject) blocks emails that fail DMARC authentication, which prevents attackers from sending email that appears to come from your domain to your suppliers, customers, and partners. Organizations that have deployed DMARC monitoring-only remain vulnerable to exact-domain impersonation of their brand; DMARC enforcement should be the foundation of any BEC prevention program.

Email Security Evaluation Checklist

Use before signing any email security contract.

Verify DMARC policy enforcement status (p=reject) — monitoring-only DMARC does not prevent exact-domain impersonation

Test detection accuracy with a live threat feed — request vendor POC using current real-world BEC and phishing campaigns

Assess gateway vs. API-based deployment trade-offs for your environment and existing mail flow architecture

Evaluate Microsoft 365 license tier — Plan 1 vs. Plan 2 capabilities differ significantly for security program requirements

Validate multi-platform coverage if you use Teams, Slack, or SharePoint for internal file sharing and messaging

Assess BEC-specific protection: executive impersonation, domain look-alike, vendor email compromise scenarios

Review security awareness training content currency — simulations should reflect current threat actor techniques, not generic phishing templates

Evaluate automated remediation capabilities — how quickly can the platform remove confirmed phishing from all mailboxes after detection?

Assess SIEM integration for email threat telemetry forwarding to security operations workflows

Model total cost including both gateway and complementary behavioral layer (Abnormal or Cofense) for comprehensive coverage

Is your email security platform missing?

Submit it for a ShipOrSkip verdict.

Submit a tool for review

Get the Email Security Tools Shortlist

Weekly verdicts on enterprise email and messaging security. No hype — ship/skip decisions for security architects and CISOs.

Bookmarks

Loading bookmarks...

No bookmarks yet

Bookmark tools to save them for later