AI-Powered Phishing: What the MDDR 2025 Reveals

By CaptainDNS
Published on October 22, 2025

  • #Phishing
  • #Microsoft
  • #IA
  • #DMARC

Bottom line: AI doesn't create a new vector; it industrializes phishing.

Why does AI tip the economics of phishing?

  • Mass personalization: Large language models (LLMs) produce emails tailored to the recipient's profile, tone, and context while erasing typos and stylistic tells.
  • Rapid iteration: Attackers test variants (subjects, calls to action, timing) and automatically keep the winning versions.
  • Automation of side tasks: OSINT collection, translation, bounce tracking, list management, simulated opt-outs-everything is scriptable.
  • Near-zero marginal costs: As crime-as-a-service expands, the price per email sent keeps dropping; defenses have to become "expensive" for the attacker again.

Diagram: relative effectiveness (CTR)

Diagram: relative effectiveness Key choke points: anti-spam/DMARC filtering, browser isolation and EDR, strong authentication (FIDO2 keys), and tight control over remote assistance tools.

Typical attack chain (and where to break it)

Typical attack chain Source: MDDR 2025.

Priority measures (practical and realistic)

  1. Strong MFA by default (FIDO2 security keys on privileged accounts, OTP for the rest). Avoid push fatigue; enable anti-phishing flows (WebAuthn).
  2. Harden email up front: SPF/DKIM/DMARC on "reject", strict alignment, subdomain policies, and continuous DMARC failure monitoring.
  3. Behavioral filtering at the mail gateway and proxy: URL detonation, reputation, detection of phishing kits and authentication proxies.
  4. Browser isolation for high-risk personas (finance, HR, executives) and Safe Links/Safe Attachments.
  5. Control RMM tools (Remote Monitoring & Management): strict allowlisting, WDAC/AppLocker, telemetry on Quick Assist & similar.
  6. Identity hardening: MFA + geofencing, session risk scoring, short-lived tokens, Continuous Access Evaluation.
  7. Disable active attachments (macros, HTA, LNK) and neutralize active SVGs (JavaScript obfuscation).
  8. Continuous exercises: short, frequent awareness campaigns, role-tailored simulations, blameless feedback loops.
  9. Escalation procedures: dedicated "phishing-SOS" channel (chat), handling within < 15 minutes, ready-to-go reset+revoke+report playbook.
  10. Look-alike domain monitoring: targeted defensive registrations, detection rules (IDN homoglyphs).

Quick ATT&CK mapping -> controls

Attacker stepTechnique (e.g.)Key controls
LureSE-Spearfishing Link (T1598)Filters, DMARC, NLP detection, browser isolation
CollectionOSINT (T1593)HR hygiene, reduced public exposure, just-enough-info
AuthMFA Fatigue / Reverse proxyFIDO2, anomaly detection, token binding
Post-compromiseUnapproved RMMWDAC/AppLocker, EDR, allowlists
PersistenceMailbox rules, OAuthOAuth auditing, rule detection, token resets

Security KPIs to track (simple and actionable)

  • DMARC pass rate (per subdomain), % of FIDO2 keys deployed on sensitive accounts, median handling time for reports, share of URLs neutralized before click, % of unapproved RMM blocked.

Sources and further reading

  • Microsoft Digital Defense Report 2025 - key numbers: AI CTR 54% vs 12% (≈4.5×), profitability up to ×50 at scale. See The threat landscape → Phishing landscape, p. 37, and references p. 84.
  • Academic study cited in the MDDR: Evaluating Large Language Models' Capability to Launch Fully Automated Spear Phishing Campaigns: Validated on Human Subjects (Heiding et al., 2024, arXiv:2412.00586).
  • Recent defense example: AI vs. AI: Detecting an AI-obfuscated phishing campaign (Microsoft Security Blog, Sept. 2025).

Note. This article favors pragmatic, high-value defensive measures suited to SMB/SME teams as well as advanced groups.