Email DLP evaluation questionnaire

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All 9 vendors in this category.

• baselineRFIWhat detection methods does the platform use to identify sensitive outbound content — keyword/regex matching, exact-data-match against a known dataset (e.g., a customer database of SSNs), or contextual/ML-based classification — and what is the measured false-positive rate for each method on real production mail volume?weight 3
  Answer key — what a strong answer shows

  Contextual/ML classification generally outperforms pure keyword matching but needs a stated false-positive rate; a vendor unable to give even an approximate production FP rate likely hasn't measured real-world accuracy.

• baselineRFPDescribe misdirected-email detection specifically — can the platform flag or block an email about to be sent to the wrong recipient (e.g., autocomplete error, similarly-named external domain) before it leaves, and quantify prevented incidents with a customer reference.weight 3
  Answer key — what a strong answer shows

  Misdirected email is one of the most common real-world data-loss incidents and a distinct capability from content-based DLP; ask for a concrete prevented-incident count from a named customer, not a generic feature claim.

• baselineRFIHow does the platform handle attachments specifically — does content inspection extend inside compressed archives, embedded documents, and images (OCR for sensitive data in screenshots), or only to the visible email body and top-level attachment text?weight 3
  Answer key — what a strong answer shows

  Attackers and careless users alike commonly exfiltrate data via nested/compressed attachments or screenshots; a platform that only inspects plain visible text has a real, exploitable coverage gap.

• baselineRFIWhat is the enforcement action model — silent block, user-facing warning with override-and-justify, encryption-on-send, or a mix depending on policy severity — and can policy differ by sensitivity tier rather than one blunt action for every violation?weight 3
  Answer key — what a strong answer shows

  Tiered enforcement (e.g., warn-and-justify for lower-risk violations, hard block for high-risk) balances security with business workflow disruption better than one uniform action for every match.

• baselineRFPDetail integration with the broader data-protection stack — does policy and incident data flow into a unified DLP/data-classification platform covering endpoint and cloud storage too, or does email DLP operate as a standalone silo with separate policy authoring?weight 3
  Answer key — what a strong answer shows

  Unified policy authoring across email, endpoint, and cloud DLP is stronger than a standalone email-only silo requiring separate, potentially inconsistent policy definitions.

• baselineRFIHow does the platform handle encrypted or password-protected outbound attachments intentionally used to evade content inspection, and what visibility exists into what's actually being sent when content can't be inspected?weight 3
  Answer key — what a strong answer shows

  Encrypted attachments are a known DLP evasion technique; a credible vendor acknowledges this blind spot and describes any mitigating control (e.g., flagging encrypted attachments to unusual recipients) rather than ignoring the gap.

• baselineRFPExplain incident-response workflow when a violation is caught — automated case creation with full context (sender, recipient, matched content, policy triggered), and whether security/compliance teams can query historical DLP incidents for pattern analysis.weight 3
  Answer key — what a strong answer shows

  Rich incident context and historical queryability matters for both individual incident response and identifying systemic policy gaps or repeat offenders over time.

• baselineRFIWhat is the deployment model relative to the customer's email platform (native API integration with Microsoft 365/Google Workspace versus mail-flow/gateway interception), and what latency does content inspection add to outbound mail delivery under production load?weight 3
  Answer key — what a strong answer shows

  API-based integration is generally lower-friction than gateway interception but can have different latency and coverage characteristics; ask for a measured latency figure under real production volume, not a lab benchmark.

• baselineRFPDetail reporting for compliance-driven use cases (e.g., demonstrating PCI DSS or HIPAA email-handling controls to an auditor) — are pre-built compliance reports available, or does the customer need to build custom reports from raw incident logs?weight 3
  Answer key — what a strong answer shows

  Pre-built, regulation-specific reports save real audit effort; ask for a specific example report rather than accepting a general 'compliance-ready' claim.

• baselineRFIWhat is the pricing model — per mailbox per month, tiered by detection-method sophistication — and does cost differ meaningfully between basic keyword matching and full ML-based contextual classification?weight 3
  Answer key — what a strong answer shows

  Look for transparent, tier-differentiated pricing that's explicit about which detection capabilities are gated behind a premium tier rather than included in the base product.

• baselineRFPFor a confirmed data-exfiltration event that evaded email DLP (a real incident, not a theoretical gap), what forensic capability exists to reconstruct exactly what was sent and to determine why the policy failed to catch it, with a customer-referenced example?weight 3
  Answer key — what a strong answer shows

  Strong answers describe a real forensic and root-cause-analysis capability for a confirmed miss, not just confirmation that detection generally works — understanding why a real evasion succeeded is essential to closing the gap.

• baselineRFIDetail historical trend reporting on DLP-blocked-event volume and violation-category trends over time, suitable for demonstrating program effectiveness to leadership.weight 3
  Answer key — what a strong answer shows

  Trend-over-time reporting is a distinct capability from individual incident logs — confirm this exists as a maintained, exportable report.

• baselineRFPWho within the organization gets access to DLP incident data, given that a DLP incident record often contains the actual sensitive content that was almost leaked — is there a strict, documented access model given how sensitive this data is?weight 3
  Answer key — what a strong answer shows

  A DLP incident log frequently contains the literal sensitive data that triggered it — ask for a specific, strict access-control model, not just generic RBAC, given the sensitivity of the incident data itself.

• baselineRFIHow does the platform integrate with the customer's existing CASB/SSPM tooling so DLP policy is consistently enforced across email and cloud/SaaS channels, rather than email DLP operating as an isolated policy silo with separately-authored rules?weight 3
  Answer key — what a strong answer shows

  Look for genuine cross-channel policy consistency; separately-authored email-only DLP rules that don't reconcile with cloud/SaaS DLP policy creates real gaps and management overhead.

• baselineRFIHow consistent is detection accuracy for non-English business communication — is contextual/ML-based classification genuinely multilingual, or does accuracy meaningfully degrade for languages other than English?weight 3
  Answer key — what a strong answer shows

  A genuinely global organization needs real multilingual detection accuracy, not just an English-tuned model with translated interface menus — ask for a specific answer on language coverage depth.

• baselineRFPWhat is the mobile email client's DLP enforcement parity with desktop — do the same content-inspection and blocking policies apply equally when sending from a mobile device, or is mobile a materially weaker enforcement environment?weight 3
  Answer key — what a strong answer shows

  Ask for an honest mobile-versus-desktop enforcement-parity comparison; a degraded mobile DLP posture is a common real gap that should be disclosed rather than assumed away.

• baselineRFIWhat migration support exists for moving from an incumbent email DLP solution — can existing policy rules, exception lists, and historical incident data be imported rather than manually rebuilt from scratch, and what is a customer-referenced migration timeline?weight 3
  Answer key — what a strong answer shows

  Strong answers describe real migration tooling and a concrete, customer-validated timeline; a vendor with no migration story is asking the customer to manually rebuild potentially years of accumulated policy tuning from scratch.

• baselineRFPThe bidder should configure the proposed DLP solution to collect O365 Email DLP alerts for a centralized dashboard, and integrate the classification solution with the financial institution's existing Azure Information Protection (AIP) — reclassifying existing AIP-tagged files seamlessly, taking ownership of AIP data classification/labelling policy shortcomings if any.weight 3

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