12 Best Phishing Simulation Tools for Microsoft 365 IT Managers: Licensing, Delivery, and Reporting Compared

The best phishing simulation tool for Microsoft 365 is the one that reaches the right employees, records their behavior accurately, and connects the result to useful follow-up. Compare Microsoft’s native Attack simulation training with specialist platforms on those jobs before comparing template counts.

Imagine your IT team supports 500 Microsoft 365 users. A phishing exercise records 35 clicks, but several employees insist they never opened the message. Meanwhile, a new hire is missing from the audience and the reporting button appears in desktop Outlook but not in the web client used by your finance team. You need to understand the delivery, roster, and reporting workflow before presenting the results to your CISO.

Threatcop is a strong choice to evaluate when you want Microsoft directory integration alongside multi-vector simulations, individual risk insights, and targeted learning. Its documentation covers Azure user and group synchronization, Microsoft Defender delivery configuration, and an Outlook reporting deployment for TPIR. Those are separate parts of the workflow, each worth demonstrating in your environment.

Microsoft Attack simulation training deserves a place in the comparison if your users already have qualifying licenses. Other tools offer different delivery methods, learning workflows, and service models. This guide compares 12 options for US IT managers and awareness owners, with product and pricing details checked on October 21, 2026.

Quick verdict: which Microsoft 365 phishing simulator should you evaluate first?

• Start with Threatcop for a connected assessment and learning program. TSAT provides attack simulations and employee risk visibility; TLMS supports personalized learning from a 2,000+ content library across eight formats. Ask for the Microsoft 365 workflow to be included in the demonstration.
• Evaluate Microsoft’s native option against licenses you actually own. Attack simulation training requires qualifying Microsoft 365 E5 or Defender for Office 365 Plan 2 licensing. Confirm the covered user population rather than assuming every Microsoft security subscription includes it.
• Compare delivery methods as a purchasing criterion. Advanced Delivery handles qualifying transport-based simulations; API insertion places messages in mailboxes through an authorized application. They have different requirements and measure different parts of the experience.
• Shortlist KnowBe4, Hoxhunt, and Mimecast Engage when their operating approach fits your team. Inspect the current Microsoft delivery guidance, employee reporting experience, and campaign administration in the proposed package.
• Include usecure, PhishingBox, Keepnet, SoSafe, and CanIPhish when direct mailbox delivery is a priority. Check permissions, supported mailbox types, post-delivery tools, and the process for resolving failed delivery.
• Consider Huntress for a managed program and Infosec IQ for awareness automation with Entra ID provisioning. Confirm who operates each task and demonstrate the precise delivery route, reports, and follow-up you intend to buy.

1. Should you use Microsoft Attack simulation training or a third-party tool?

Start with the requirement your existing environment does not satisfy. Your team may need a practical simulation program, broader social-engineering coverage, better learning follow-up, less administration, a particular reporting experience, or a managed service.

The decision should include the native option when it is available to your users. An existing entitlement can change the economics. It does not, by itself, establish that your audience, reporting, content, and operating requirements are covered.

Use this table to set up a fair comparison. A specialist should earn its place by solving a defined requirement, while the native option should be evaluated with its real operating workload and current entitlement.

Define the gap in one sentence

A useful requirement sounds like: “We need to identify employees who repeatedly respond to invoice impersonation and assign relevant learning without rebuilding the audience every month.” Another might be: “We need a managed monthly program because our IT team cannot operate campaigns consistently.”

Those requirements lead to different shortlists. Threatcop is particularly relevant to the assessment-to-learning requirement. Huntress is worth evaluating for managed program operation. Microsoft’s native option remains relevant when its demonstrated scope and your licensed environment meet the brief.

2. How do the 12 phishing simulation tools compare for Microsoft 365?

The table focuses on documented Microsoft-related capabilities and the requirement each vendor should demonstrate. It is a comparison of selection angles, rather than a measured effectiveness ranking or a set of customer star ratings.

Pick three or four options that match your operating needs. Then use the same representative audience, reporting requirement, and follow-up scenario in each demonstration.

3. Which phishing simulation tool fits your Microsoft 365 environment?

1. Threatcop: Microsoft directory integration with assessment and learning

Threatcop’s Microsoft Azure integration guide documents connecting domains, selecting groups, and synchronizing users, including an Auto Sync option. Its Defender simulation-delivery guide covers configuring Advanced Delivery with the relevant sender and simulation information.

Those capabilities support a practical program when combined with Threatcop’s assessment and learning offering: simulate relevant attacks, inspect individual risk, assign suitable learning, and track the result. The learning library includes 2,000+ items across eight formats.

Best fit: IT managers and awareness owners who want a Microsoft-connected audience and a broader employee assessment-to-learning workflow.

What to demonstrate: synchronize a representative group, run an approved exercise, inspect a risky action, and follow it into relevant learning and a management report. Include a new hire and an employee who changes groups.

Pricing and scope: request TSAT, TLMS, covered users, support, and required reporting in the proposal. Directory synchronization does not establish API mailbox insertion. Have Threatcop identify the actual delivery route for your tenant. If Outlook reporting is part of the requirement, demonstrate the separately scoped TPIR workflow as well.

2. Microsoft Attack simulation training: evaluate the native licensed option

Microsoft’s getting-started documentation requires Microsoft 365 E5 or Defender for Office 365 Plan 2 licensing. It describes simulations, training assignments, multiple payload techniques including OAuth consent, and QR-code links for supported techniques. On-premises mailboxes are supported with reduced reporting functionality.

Best fit: organizations with qualifying licenses whose simulation, learning, and reporting requirements can be met in the Defender workflow.

What to demonstrate: create a representative campaign, select the intended audience, show the assignment rules, and produce the report your awareness owner will use. Include the actual mailbox and client types in your environment. The native product has automation and learning capabilities; compare their demonstrated fit rather than assuming they are absent.

Pricing and scope: Microsoft’s US product page lists Defender for Office 365 Plan 2 at $5 per user per month, paid yearly, checked on October 21, 2026. It includes broader security capabilities as well as simulation training. Confirm existing entitlement before estimating any incremental license purchase.

An Attack Simulation Administrator role is among the documented options for campaign operation. Separate routine campaign ownership from the higher-privilege work involved in establishing or changing integrations.

3. KnowBe4: a dedicated awareness program with current delivery guidance

KnowBe4’s Whitelisting Guide, updated October 5, 2026, recommends Microsoft Advanced Delivery for Microsoft 365 users. It also discusses additional filtering and mail-route considerations. Use the current guide rather than assuming an old integration recipe remains the recommended approach.

Best fit: teams comparing a dedicated simulation and learning program with Microsoft’s native option, especially when campaign administration and content requirements are central to the decision.

What to demonstrate: show the delivery route through your actual email-security environment, the campaign audience, and a change to an existing campaign. Then show the learning assignment and the report an IT manager needs for follow-up.

Pricing and scope: request a proposal specifying the awareness level, simulations, content, reporting, integration support, and any services. If the presentation includes a different delivery method, ask for the current supported documentation and prerequisites for that method.

The important comparison is the supported operating workflow. A familiar product name or an existing allowlisting configuration should not substitute for a delivery and reporting check in the environment you intend to use.

4. Hoxhunt: adaptive practice with an Outlook reporting experience

Hoxhunt’s Receive Connector guidance describes directing simulation messages to Microsoft 365 or on-premises Exchange, including hybrid-environment considerations. Its add-in verification guidance distinguishes technical deployment checks from confirmation that the button is visible in the employee’s Outlook client.

Best fit: organizations prioritizing recurring practice and employee reporting, with a team prepared to validate the supported mail route and client experience.

What to demonstrate: follow one simulation report from Outlook into the platform’s handling workflow. Repeat the test in the clients your staff use. Include a genuinely suspicious-message reporting example in a controlled demonstration so the security team understands the difference in handling.

Pricing and scope: request the training and response capabilities required for your program. Confirm the reporting detail, client support, implementation assistance, and work retained by your team.

Do not stop at an administrative deployment status. Your employee-facing pilot should show the button, the feedback, and the resulting record in the exact client configuration used by the selected group.

5. usecure: Graph-based message injection with explicit permission context

usecure’s Microsoft message-injection FAQ, dated May 8, 2026, describes an administrator-approved Entra enterprise application using Microsoft Graph application permissions. It identifies Mail.ReadWrite as the permission used to place simulated messages into mailboxes.

Best fit: teams evaluating direct mailbox placement as part of a phishing and awareness program.

What to demonstrate: use a limited approved audience and show successful delivery, a recipient error, the resulting behavior record, and the learning follow-up. Have the administrator identify the application, permission scope, and process for reviewing or revoking access.

Pricing and scope: request the required phishing, learning, reporting, and service components for your user population. Confirm which modules and operating tasks the proposal covers.

Message insertion can help isolate employee behavior from upstream mail filtering. It also makes the integration’s permission model part of the purchasing decision. Review both the documented intended use and the access the application is technically authorized to exercise, then establish the ownership and scope appropriate for your tenant.

6. PhishingBox: direct delivery with mailbox and tenant constraints

PhishingBox’s Direct Delivery guide, updated August 18, 2026, describes Microsoft Graph delivery at account or group level. Recipients must have active mailboxes in the connected tenant; alias addresses are not supported for this delivery method. The guide also states that Microsoft Direct Delivery is not compatible with GCC High tenants.

Best fit: campaign operators who want to evaluate direct mailbox delivery and control how it is configured across the account or selected groups.

What to demonstrate: compare the address in your campaign audience with the primary mailbox identity. Show how the system handles a renamed user, an alias, and an out-of-tenant recipient. Then confirm which account or group setting determines the delivery method.

Pricing and scope: request the required simulation, learning content, reporting, and support package. If you operate a government tenant or use specialized mailbox arrangements, settle eligibility before conducting a broader product evaluation.

A delivery method can be suitable for the majority of your audience while leaving exceptions. Require those exceptions to appear in a usable report so they do not disappear into an apparently successful campaign total.

7. Keepnet: two Microsoft delivery approaches to compare

Keepnet’s Microsoft 365 documentation offers Direct Email Creation or allowlisting. Direct Email Creation places simulation messages in the inbox through API permissions, while the documentation notes that URL-protection tools may still need separate consideration.

Best fit: teams that want to choose a supported delivery approach explicitly and evaluate how it affects employee-behavior measurement.

What to demonstrate: ask the team to show the selected path in your mail architecture, including the learning page and any URL inspection after delivery. Then inspect an event that could have been generated by automated scanning and see how it is treated in the report.

Pricing and scope: request the simulator, learning, channels, reporting, integrations, and support your program needs. Keep any additional voice, SMS, or other channel requirements separate from the Microsoft email-delivery decision.

The product’s delivery documentation gives you a useful starting point, but the pilot should settle the operational questions: which route is selected, which checks still apply, how exceptions are handled, and what the administrator must maintain over time.

8. SoSafe: DMI and traditional delivery paths with follow-up configuration

SoSafe’s Microsoft 365 guidance, updated October 1, 2026, recommends Direct Message Injection while retaining traditional allowlisting as an alternative. The documented DMI path also includes steps concerning simulation links and image display.

Best fit: awareness leaders evaluating a platform with a documented Microsoft delivery path and employee-learning experience.

What to demonstrate: deliver an approved message, open its learning page, inspect its images and links, and complete the intended follow-up in a representative Outlook client. Have the administrator show any configuration needed for security tools that act after delivery.

Pricing and scope: request the required learning, simulations, reporting, and optional service scope. Confirm the features available in the proposed package and the responsibilities your IT team retains.

Treat “direct injection” as the start of a delivery explanation. It does not remove the need to test the rest of the experience. Your team still needs to confirm that the message, link, feedback, learning activity, and reporting path work together in the supported environment.

9. Huntress Managed SAT: Microsoft synchronization within a managed program

Huntress’s Graph synchronization guide, updated March 3, 2026, describes synchronizing learners through Microsoft and opting into API-based message insertion. Its Microsoft delivery guide explains that delivery can depend on how the provider integration was configured, including API and SMTP paths.

Best fit: lean IT teams comparing managed awareness operation with running the program themselves.

What to demonstrate: show how the audience is maintained, which delivery method applies, what happens when that path fails, and how the operator resolves the exception. Then generate the progress and follow-up report your internal owner will receive.

Pricing and scope: request a proposal for your user count and purchasing route, including any partner services. Define which tasks Huntress, a service provider, and your internal team perform.

A managed program can reduce recurring campaign work, but Microsoft administration and organization-specific decisions still need owners. Ask who will investigate a delivery issue, approve a configuration change, and communicate with affected employees when an exception occurs.

10. Mimecast Engage: simulation delivery within an existing security environment

Mimecast’s Engage Advanced Delivery guide, updated April 23, 2026, applies to Engage Core and Pro. It describes configuring Microsoft delivery using the relevant sender information and hosting-specific details.

Best fit: organizations evaluating awareness alongside a broader Mimecast environment, particularly where the email-security owner will participate in implementation.

What to demonstrate: map the route a simulation follows through your tenant and other email-security systems. Show the resulting message, a user interaction, and the report. Include an example that distinguishes an employee action from automated inspection.

Pricing and scope: confirm the Engage package, contributing security products, reporting, deployment assistance, and services. Do not assume existing Mimecast email-security ownership establishes every awareness entitlement.

Ask the team to use configuration details appropriate to your hosting location and actual environment. A copied example from another deployment is less useful than a demonstrated message path, a clean behavior record, and a named owner for future changes.

11. Infosec IQ: awareness automation with Entra ID provisioning

Infosec IQ’s product page explicitly describes learner provisioning through Microsoft Entra ID, personalized assignments, phishing simulations, and progress reporting. These capabilities make it relevant to a Microsoft-connected awareness shortlist.

Best fit: teams that want roster automation alongside a structured learning and simulation program.

What to demonstrate: synchronize the selected learners, show the current supported Microsoft email-delivery route, run an approved exercise, and trace the result into training and reporting. Include a transfer between departments so you can see whether the learning and reporting audience stay aligned.

Pricing and scope: request the content, simulations, learner provisioning, reports, and support needed for your organization. Have the vendor provide the current delivery documentation for the proposed configuration.

Entra ID integration establishes a provisioning capability; it does not tell you whether a campaign uses SMTP, API insertion, or another supported route. Keep those questions separate during procurement. This lets you compare Infosec IQ’s awareness workflow on its demonstrated merits without inferring a delivery mechanism from the directory-integration label.

12. CanIPhish: self-service evaluation with documented direct injection

CanIPhish’s Microsoft injection guide, updated April 24, 2026, describes using Microsoft Graph to insert simulation and notification messages. It documents application permissions including Mail.ReadWrite and User.Read.All. It also notes that Graph cannot inject messages into mailboxes hosted on an on-premises Exchange server in a hybrid arrangement.

Best fit: IT managers who want a self-service platform to evaluate and can validate the permissions, mailbox hosting, and operating workflow.

What to demonstrate: show a supported mailbox, a recipient outside the connected tenant, an error, and the resulting campaign record. If your environment is hybrid, establish the delivery path for each mailbox population.

Pricing and scope: the pricing page, checked on October 21, 2026, offers a free plan for up to 10 employees. Professional has an 11-user minimum and Enterprise a 25-user minimum, with Enterprise billed annually. Use the live calculator or a written quote for a paid total at your headcount and selected tier.

A small evaluation can establish workflow fit. It should not be treated as proof that every client, mailbox arrangement, or feature needed in production has been covered.

4. What does Microsoft 365 phishing simulation cost?

Separate existing license entitlement from a new license purchase and from internal operating effort. Microsoft’s public Plan 2 price covers a broader email-security product, while a specialist quote may include different training, channels, services, and support.

For 500 newly licensed users at the public $5 Plan 2 rate, the arithmetic is $2,500 per month and $30,000 per year. This is the full Plan 2 subscription calculation, rather than a standalone charge for Attack simulation training. Your Microsoft agreement and existing entitlements determine the actual incremental cost.

Compare proposals against the same requirement

Suppose your 500 intended users are already licensed for the native option. Plan for six internal hours a month to operate the native program, at an assumed internal rate of $75 per hour. Compare that with a specialist proposal assumed to cost $12,000 annually and require two internal hours a month.

In this scenario, the specialist costs $8,400 more per year after the assumed time saving. It needs to justify that difference through requirements the team values, such as learning suitability, additional channels, reporting, or service support. Replace the assumed hours and proposal with your pilot results and actual quote.

If all 500 users instead need a new Plan 2 purchase at the public rate, adding the $30,000 license calculation to the assumed $5,400 operating effort gives $35,400 annually. Include the value of Plan 2’s broader security capabilities in that decision; it would be misleading to allocate the whole purchase to phishing training while ignoring the rest of the product.

Price the Threatcop workflow you intend to operate

Ask Threatcop to scope TSAT simulation and assessment, TLMS learning, users, support, and your Microsoft integration requirements. Add TPIR only if employee reporting and email analysis are part of your selected workflow.

A useful proposal identifies both the subscription and the work needed to make it useful: audience maintenance, content selection, delivery validation, learning follow-up, and management reporting. Compare those outputs with the native option and other shortlisted platforms.

5. How do Advanced Delivery and direct message injection differ?

Delivery architecture changes what the exercise measures. A controlled simulation intended to reach employees is different from a test of whether your email-security filters detect an incoming threat. Define that purpose before choosing the route.

Microsoft’s Advanced Delivery documentation states that the third-party simulation policy requires a message to traverse the transport pipeline. Direct injection bypasses that transport path, so the policy does not apply to those injected messages.

Use different acceptance criteria for the last row. An exercise delivered through an approved exception, or placed directly in a mailbox, cannot establish that normal inbound filters would have allowed the same threat.

Follow the entire delivery path

A third-party gateway, on-premises Exchange, cloud mailbox, URL-protection service, endpoint scanner, and employee reporting tool can each affect the experience. Ask the vendor and your messaging administrator to draw the actual route and identify the intended configuration at each stage.

Microsoft’s Advanced Delivery guidance also describes limits for certain in-and-out routing and internal-message scenarios. Resolve those against your environment before treating a sample configuration as a production design. Keep the buying discussion focused on a supported route and a repeatable test.

Test what happens after the message arrives

Inbox placement is only one checkpoint. A post-delivery tool may inspect the message, a browser may block the learning page, or a reporting workflow may create another automated interaction.

Have each shortlisted provider demonstrate the complete sequence: message arrives, employee sees it, link or attachment behaves as intended, feedback is understandable, learning can be completed, and the report records the right action. Keep the associated support responsibilities in the proposal.

6. Which directory, permission, and mailbox requirements matter?

Separate audience synchronization, message delivery, and employee reporting. A product may integrate with Microsoft for one of those purposes while requiring a different application, permission, or configuration for another.

This is especially important for IT managers reviewing a feature matrix. “Microsoft integration” is a starting label. Your purchasing record should explain what information moves, which action the integration performs, and who can change it.

Use these as demonstrations, rather than treating them as universal product defects. The goal is to identify the configuration and operating responsibility for your environment.

Compare permission scope with the integration’s purpose

Directory read access and mailbox read/write access authorize different operations. Several direct-injection guides document broad application permissions even when the intended use is limited to delivering simulated messages. Ask for the exact permissions in the proposed method and any supported mailbox-scoping options.

Threatcop’s Azure directory guide, for example, documents a roster synchronization workflow. Keep that distinct from its Defender delivery guidance and the TPIR add-in. This separation gives your administrators a clearer implementation plan and prevents one working integration from being used as proof that the rest is finished.

Check hybrid and specialized tenants early

Map which users have cloud-hosted mailboxes and which have on-premises mailboxes. A cloud identity does not necessarily establish that a Graph-based delivery method can reach the mailbox behind it.

Also identify government cloud or other specialized tenant requirements before shortlisting on price. PhishingBox’s documented GCC High exclusion for Direct Delivery is a concrete example of why the exact delivery method matters. Ask each provider about your tenant type without generalizing one product’s limitation to the whole market.

Assign an integration owner and an operating owner

The person authorized to approve an application may not be the person running monthly campaigns. Establish who approves the initial configuration, who maintains it, who notices a sync failure, and who resolves an unexpected delivery result.

The handover should include a tested configuration record and a clear support path. When the awareness manager starts the next campaign, they should know where to look for roster and delivery issues rather than discovering ownership during a failed launch.

7. How should Outlook reporting and learning follow-up work?

The employee should know how to report a suspicious message in the client they use, and the security team should know where that report goes. Demonstrate the report path rather than stopping at an add-in deployment status.

Threatcop’s TPIR Microsoft 365 setup guide describes deployment through Microsoft 365 Integrated Apps to selected users or groups. If TPIR is part of your purchase, include its actual employee and security-team experience in the pilot.

Validate the clients your employees use

Choose representative Outlook web, desktop, and mobile configurations from your own environment. Ask the vendor to identify the supported combinations and show the reporting experience for each one in scope.

Hoxhunt’s deployment documentation makes a useful distinction: technical checks cannot reliably establish that a button has rendered in an end user’s Outlook client. A visible button, an accepted report, and the correct resulting record are better acceptance evidence than a successful deployment command alone.

Keep native and vendor reporting paths explicit

Microsoft’s Attack simulation training FAQ says simulation messages reported through non-Microsoft tools are not captured in its attack simulation reports. If your organization uses a third-party report button with native campaigns, demonstrate the resulting data path before relying on a reporting-rate chart.

Ask where a simulated report appears, where a real suspicious email appears, what feedback the employee receives, and which team owns the response. A simulation can be recognized correctly in one system while leaving another report incomplete.

Follow a risky action into suitable learning

After a person submits information in an exercise, your team needs an appropriate next activity. Have the vendor show the rule, selected content, notification, completion, and subsequent assessment.

For Threatcop, connect the TSAT result to the proposed TLMS learning workflow. Inspect the content the employee receives and the administrator’s view of overdue or completed assignments. The value is a repeatable follow-up process that your awareness owner can operate and explain.

8. How do you keep Microsoft 365 simulation reports accurate?

Report delivery and observed behavior as separate measures. A sent campaign does not establish that every target received the message, and a recorded interaction does not always establish that an employee performed it.

Microsoft’s FAQ identifies security applications and automated inspection as possible sources of unexpected click telemetry. Use that as a reason to investigate a disputed event with supporting evidence, rather than automatically accepting or dismissing an employee’s account.

This structure gives a CISO a more useful account of the campaign than a single click-rate number. It also gives the IT manager a place to explain unresolved technical issues.

Use the delivered population in the calculation

Suppose your campaign targets 500 users, excludes 20 ineligible identities, and fails to deliver to another 30. That leaves 450 delivered messages. If 36 recipients click, the delivered-message click rate is 8%.

Dividing the same 36 clicks by the original 500 targets gives 7.2%, which answers a different question. Keep the denominator beside the rate and preserve the 50 exclusions or delivery failures in the report.

Separate recorded events from confirmed employee behavior

Imagine 40 click events appear in the report, and your investigation attributes 15 to automated inspection. If those are 40 distinct recipient-level click records with no overlap, the remaining 25 represent 5% of a 500-person delivered audience. If the raw records overlap or contain repeated events, deduplicate them before calculating a user rate.

The point is to make the event definition visible. A tool should help the administrator explain the distinction between message delivery, raw interactions, unique recipients, and confirmed employee actions.

Preserve comparable conditions between campaigns

Keep the audience, scenario type, observation period, and important delivery differences beside any trend. A change from an externally delivered exercise to API insertion changes the test conditions and can affect how you interpret the result.

Use comparable cohorts for improvement reporting. If the next campaign reaches a smaller or different group, say so in the management report. Your team can still learn from the exercise without attributing every change in the chart to training effectiveness.

9. What do verified customer reviews tell you to test?

These individual reviews describe platform experiences and useful evaluation questions. They are not independent audits of current Microsoft permissions, client compatibility, or every feature in a proposed subscription.

Threatcop: make the follow-up relevant and understandable

Akshat V., a cybersecurity engineer at a company with 50 or fewer employees, highlighted “interactive and hands-on training” in a G2 review dated June 10, 2026. G2 identifies a validated reviewer and a G2 invitation, without a G2 incentive.

raktim p., an administrator at a company with 51–1,000 employees, praised an “ample amount of real life examples” in a G2 review dated June 10, 2026. G2 labels the review validated and organic.

Use these experiences to shape your content demonstration. After a Microsoft-connected exercise identifies a weakness, inspect whether the proposed Threatcop learning activity addresses that weakness in language employees can use.

KnowBe4: test campaign changes after the initial setup

A Verified User, Manager in Information Technology at a consumer-goods company with 51–200 employees listed “Automated training” as a strength in a vetted TrustRadius review dated April 30, 2026. The review also requested easier changes to existing campaigns and discussed multiple Microsoft 365 tenants. Incentive status is not exposed on the page.

Ask your shortlisted providers to demonstrate a change after a campaign has been created. Record what can be changed directly, what requires a replacement campaign, and what happens to the existing results.

Hoxhunt: validate the employee’s reporting experience

A Verified User, Engineer in Information Technology at an IT-services company with 51–200 employees praised the “Easy to use to report button for Microsoft Outlook application” in a vetted TrustRadius review dated October 2, 2024. The reviewer described more than 100 employees participating; incentive status is not exposed on the page.

This supports testing the reporting workflow in the clients your workforce uses. Check the current supported configuration and follow the report into its destination rather than inferring compatibility from an older review.

PhishingBox: include administrator learning effort

Danny S., an owner at a company with 50 or fewer employees, wrote “Learning the platform takes a little time” in a G2 review dated July 9, 2026. He also said the platform becomes easy to use once understood and described using its LMS and reselling the phishing platform. G2 identifies a current-user, validated, incentivized review collected through a seller invitation.

Include onboarding time and recurring administration in your evaluation. The comparison should reflect what your operator can do after the guided demonstration, including resolving a delivery exception.

Huntress: inspect the detail behind the progress report

Sam G., a Level 2 support engineer at a company with 51–1,000 employees, praised “tracking progress and following up much easier” in a G2 review dated July 16, 2026. The same review requested more reporting detail and campaign customization. G2 labels it current-user, validated, incentivized, and collected through a seller invitation.

For a managed proposal, have the provider generate the report your internal owner will receive. Check whether it shows the exceptions and actions your team needs, alongside completion and participation.

10. What should a Microsoft 365 phishing simulation pilot prove?

Use a pilot to settle fit, delivery, reporting, and retained work. It should leave your team with a demonstrated workflow and a proposal that matches that workflow.

Choose an approved group that represents your actual environment. A 30-person pilot, for example, might include 10 staff using Outlook web, 10 using desktop Outlook, and 10 using the mobile or other supported configurations you need to evaluate. This is a planning choice for coverage, rather than a sample that can establish company-wide security effectiveness.

A pilot passes when the relevant requirements are demonstrated and any remaining conditions are understood. A successful send to one administrator’s mailbox is useful evidence, but it covers only that narrow configuration.

Inspect the native preview before the wider pilot

Microsoft’s simulation creation guide includes a Send a test option on the review page. Use that preview to inspect the payload, then validate the approved pilot across your representative recipients and clients. A preview sent to the current administrator is a content check; the broader pilot establishes the in-scope employee experience.

Give all vendors the same acceptance scenario

Ask each provider to handle the same business-themed simulation, report, learning assignment, and exception. Keep the content appropriate to your approved program and avoid collecting real credentials or confidential business information during a test.

Include a new employee, a renamed account, and a user who cannot complete the assignment on schedule. These cases reveal the work your operator will face during normal program administration.

Test the handover to your team

Have the intended administrator build or repeat a campaign and generate the report. Record time spent on audience maintenance, content selection, delivery checks, exception handling, and follow-up.

If the proposal is managed, replace “administrator repeats the campaign” with a demonstration of the service handoff. Show what your team approves, what the provider executes, and how an unresolved exception returns to the right owner.

Retain the configuration and change record

Document the selected delivery method, related applications, audience rules, report path, and support contacts. Agree how changes will be reviewed when a vendor updates its sending infrastructure or your organization changes its mail route.

That record makes the program easier to maintain and the next campaign easier to explain. It also helps a new IT manager understand why the environment was configured a particular way without reconstructing the original implementation conversation.

11. Which option should your IT team choose?

Choose a platform against the workflow your team can demonstrate and sustain. Threatcop belongs near the top of the shortlist when your goal is Microsoft-connected assessment, individual risk visibility, and relevant learning follow-up across a broader people-security program.

These are starting routes rather than exclusive capabilities. A final shortlist should reflect the requirements, mailbox population, and administrative capacity your organization actually has.

Build the Threatcop demonstration around your Microsoft environment

Bring your audience structure, supported Outlook clients, current mail route, and one recurring social-engineering concern to the discussion. Ask Threatcop to show the directory connection, approved campaign delivery, employee risk view, targeted learning, and report your CISO will use.

If employee email reporting is in scope, add the TPIR reporting workflow explicitly. Keep its deployment and commercial terms visible alongside TSAT and TLMS.

Book a Threatcop demo around that requirement. Compare the demonstrated workflow and scoped proposal with the same requirement in Microsoft’s native option and your other shortlisted platforms.

FAQ

Sara Abraham

Cyber Security Specialist

Department: Compliance, Threatcop

Sara Abraham is a Cyber Security Specialist at Threatcop, where her extensive expertise in the field is instrumental in strengthening the company’s cyber security initiatives. She is a key contributor to the company’s mission of providing top-notch security solutions.

Sara Abraham

Cyber Security SpecialistDepartment: Compliance, ThreatcopSara Abraham is a Cyber Security Specialist at Threatcop, where her extensive expertise in the field is instrumental in strengthening the company's cyber security initiatives. She is a key contributor to the company's mission of providing top-notch security solutions.