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Background · 1 Offensive Tradecraft

Social Engineering & Phishing.

Pretext design, channel selection, and the patterns specific to phishing privileged users — including the failure modes that turn a campaign into an internal incident on your side.

Pretext-design — what works

  • Aligned with real work. Reference an actual ticketing system, an actual vendor, an actual quarterly process. OSINT first, write second.
  • Plausible CTA. "Confirm your timesheet by Friday" beats "Verify your password now." The action requested is something the target would expect to do anyway.
  • No escalation pressure. "Urgent — locked account in 1 hour" trips the training reflex. Legitimate IT rarely uses countdown threats.
  • Look like the system, not like an attacker. Office 365 legitimate notification → copy the HTML structure, headers, footer, unsubscribe link. Diff vs. a real one until they're indistinguishable.
  • Right sender. Spoofed display name + neighboring-domain typosquat. Targets read the display name; only ~5% check the actual From: header.

Channel tradeoffs

  • Email. Highest volume, lowest conversion. Defended by mail gateways, sandbox detonation, URL rewriting. Plan for 5–15% click rate on first send.
  • SMS (smishing). Lower volume capacity, higher conversion. Sandbox doesn't exist for SMS the way it does for email. Plan for 20–35% click rate when pretext is sharp.
  • Voice (vishing). Highest conversion against helpdesk staff. Hardest to script. Most effective on Monday mornings when ticket volume is highest.
  • In-person / physical. Tailgating, dropped-USB. Highest legal/scope risk. Always written-authorized with on-call white cell contact.
  • Supplier impersonation. Email from a known vendor with a known payment-detail change request. Very high conversion against finance teams; high legal scrutiny.

Targeting admins specifically

  • Tooling-trust. Admins click links from tools they use daily — Jira, Confluence, PagerDuty, GitHub. Pretext that looks like a notification from one of those.
  • Helpdesk pretext. Reverse the direction. You call as a user with an authentic-looking ticket reference; ask helpdesk to push an MFA, claim "phone broke", get a temporary code.
  • Console-link redirect. URL that lands on a real admin console first, then redirects to your harvester. Browser security indicators show "secure" because the first hop was real.
  • OAuth consent phishing. Don't phish password; phish an OAuth scope grant. The target sees a real Microsoft consent page and clicks Allow.

Operational guardrails (don't burn the engagement)

  • Written scope, named targets only. No improvising new recipients mid-campaign.
  • Credentials handled by one operator. Captured creds never sit in a shared inbox or chat. Hash them at capture, store the hash, decrypt only at use.
  • Sender infra cleanly attributable on request. Don't reuse domains across clients. Don't reuse the SAME domain you used for actual blue-team work last quarter.
  • Kill switch. Single command that takes down all landing pages, revokes captured tokens, and notifies white cell. Test it before campaign launch.
Rule of thumbThe cleanest phishing campaign is the one the blue team learns the most from. Maximize that, not raw click rate. A 40% click rate with no detection-loop feedback teaches nothing; a 12% click rate that the SOC catches in 11 minutes is a successful exercise.

From reference to evidence

Run this against your own environment.