Phishing Drills with Microsoft: Attack Simulation That Works

Design Simulations That Mirror Your Real Phishing Risks

Understand Your Actual Threat Landscape

A phishing resilience program has value only when simulations reflect your real risk profile. Begin by mapping phishing patterns that target your people and workflows. Common scenarios include supplier impersonation for accounts payable, fake shared file invitations for client services, MFA-reset scams aimed at administrators, and payroll change requests that target HR.

Look at recent email security alerts and user-reported phish submissions to identify the techniques that are getting through. These might include attachments with macros, QR codes, fake links that mimic trusted brands, or domains that look very similar to legitimate ones.

Speak with team leads to discover which external services and third-party portals your staff interacts with most often. Simulations that mirror these familiar brands and services tend to be more realistic and more effective at uncovering risky behavior.

Set Clear Goals for the First 90 Days

Define what success means for your first several simulations. Clear, behavior-focused targets help guide improvement:

• Increase phishing report rates to 20–30 percent for difficult scenarios

• Reduce failure rates (clicks or form submits) to below 5–8 percent

• Shorten median time-to-report to under 15 minutes

Plan a mix of campaign difficulty levels. Broad audiences may receive straightforward lure types, while higher-risk roles such as finance and IT may receive multi-step baits. It is important to foster a learning culture, not a punitive one. Thank people who report simulated phish, share anonymized insights from each simulation, and provide short micro-training immediately after a campaign to reinforce learning.

Tie Simulations to Control Improvements

Use simulation outcomes to guide changes in your technical controls. If credential-harvesting links are effective, strengthen Conditional Access policies and enforce phishing-resistant MFA for administrators. If QR-code based lures succeed, adjust attachment and URL inspection policies to block embedded links in images, and train staff to verify links through an out-of-band channel.

Microsoft outlines how to begin with Attack Simulation Training and describes which licenses include it in its “get started” documentation for Defender for Office 365 Attack Simulation Training. You can find it here: Attack Simulation Training - Get Started.

Set Up Microsoft 365 Attack Simulation Training End-to-End

Confirm Licensing and Permissions

Microsoft Defender for Office 365 includes Attack Simulation Training, which lets you run realistic phishing campaigns and automatically deliver targeted training to users who need it. Confirm that your organization has the right license, such as Defender for Office 365 Plan 2 or Microsoft 365 E5. Also ensure that security administrators have the permissions needed to configure and run simulations.

Microsoft’s step-by-step guide shows core setup details, from selecting a simulation type to choosing payload templates: How to Run Attack Simulations for Your Team.

Build Your First Campaign

Define a clear hypothesis for your campaign. For example, you might test whether your finance team is susceptible to vendor invoice lures that mimic a real supplier domain.

Choose a prebuilt simulation template that uses realistic branding, set a delivery window that aligns with business hours, and include the report phish button in Outlook and other client toolbars to give users an easy way to respond. Target specific groups using Azure AD group membership (such as finance, HR, or IT) while excluding sensitive break-glass or service accounts.

To scale your program beyond one-off tests, use simulation automation so scenarios rotate continuously without manual effort. Microsoft’s automation tutorial walks through how to set this up: How to Setup Attack Simulation Training for Automated Attacks and Training.

Pair Simulations with Adaptive Training

After a simulation, users who clicked or engaged with a payload should receive targeted, short training modules that address the exact lure type they encountered, such as recognizing malicious QR codes or spotting subtle domain typos. Managers should plan time for this micro-training in the same week a campaign runs so learning is immediate.

For advanced risk roles such as administrators, incorporate tabletop drills that practice incident response steps like isolating affected systems, revoking sessions, and rotating credentials. As your program matures, include more sophisticated lures like OAuth consent scams and SMS-based phishing to mirror evolving attacker tactics.

Measure, Coach, and Automate to Raise Resilience Quarterly

Track Key Metrics Every Month

Measurement is the foundation of resilience. Track the following metrics each month to understand progress and trends:

• Report rate: percentage of users who flagged the simulated phish

• Failure rate: percentage of users who clicked or submitted credentials

• Time-to-report: median minutes from delivery to first report

Break these metrics down by department and simulation type so you can tailor coaching where it matters most.

Use Insights to Adjust Controls and Coaching

Report improvements publicly within your organization. Share short “spot the tell” screenshots that show what cues users missed and why a message was suspicious. Feed your simulation data back into your email and security controls. If simulations regularly bypass filters, adjust anti-phishing policies and refine Safe Links and Safe Attachments settings. If reporting takes too long, simplify or remind users about the reporting button.

Automate to Sustain Progress

Use simulation automation to maintain a regular cadence. A typical pattern might include a light campaign every month and a more advanced, deeper drill quarterly. Pair this automation with automatic training delivery so users who need reinforcement get it without manual effort.

Maintain a help desk runbook that outlines how to handle a real phish report: preserve the evidence, check for mailbox forwarding rules, evaluate sign-in risk, and reset sessions if needed. During incident post-mortems, compare simulation metrics to real-world detections to validate that behaviors are improving where you need them most.

Document Outcomes for Leadership and Audits

Summarize trends and align them with changes in your controls. For example, you might report: “Report rates increased by 12 points, risky sign-ins dropped after enforcing phishing-resistant MFA, and containment time decreased by 40 percent.”

Microsoft’s documentation remains your definitive reference for features and setup. Start with the Attack Simulation Training documentation and expand with Defender for Office 365 tools as your program grows.

FAQ

What is phishing simulation in Microsoft 365?

Phishing simulation in Microsoft 365 uses Microsoft Defender for Office 365 Attack Simulation Training to send controlled, realistic phishing scenarios to users. These simulations test how users respond and deliver adaptive training based on their actions. The official guide is here: Attack Simulation Training - Get Started.

What licensing is needed for Microsoft phishing drills?

To run Attack Simulation Training, you typically need Microsoft Defender for Office 365 Plan 2 or Microsoft 365 E5 licenses. These plans provide the simulation and reporting features discussed in Microsoft’s setup guides.

How do I choose simulation scenarios?

Start by mapping real phishing risks specific to your organization. Review previous email security alerts and user-reported phish, interview team leads about the external services they use, and design simulations that reflect the tactics your staff encounters. This approach improves realism and educational value.

What metrics should be tracked to measure improvement?

Key metrics include the report rate, failure rate, and time-to-report. Track these monthly and segment by department and scenario type to identify where coaching is most needed.

How often should phishing simulations run?

A balanced cadence could include one light campaign each month and an advanced, more complex drill quarterly. Forging a regular rhythm helps sustain awareness without overwhelming users.

How can training be delivered after simulations?

Pair simulations with adaptive training that addresses the specific lure used. Provide short modules focused on recognizing QR code traps, domain look-alikes, or fake login pages. Adaptive training increases relevance and retention.