Stung by my own stupidity

If you aren’t aware, when you built or run anything new in Copilot Studio it will all be charged PAYG against Azure. To allow this you need to connect your Power Platform environment to an Azure subscription. You can find details on how to do that here:

https://blog.ciaops.com/2022/04/29/set-up-payg-for-power-platform/

Now with all that in place I built a new modern agent in Copilot Studio to answer M365 questions (called Sage) built using the new Github Copilot harness and using Claude Opus 5 as the LLM.

image

I then tested it a few times in ‘Preview’ and was happy that it was all working. I knew at this point, all that was going to cost me a few bucks because now even creation costs with the new Copilot Studio. All good so far and still in budget.

Next, I wired up a new Workflow in Copilot Studio to wait for a message to be posted into a Microsoft Teams channel, take that, post it to the newly created Sage agent, then take the reply from the agent and post it back into the same channel. Quick and easy to create. Job done, I thought.

Can you see the logic flaw yet? I certainly didn’t initially. In short, the workflow I created basically replies to every message posted into a channel. Ahem, those replies then trigger the agent to run again and post yet another message, which again triggers another message posting from the agent, and on and on. So, I had created an infinite loop.

My mistake was now running the workflow and calling the agent and posting into the Team every minute or so. I didn’t recognise my error for a few hours! Yes, hours. I estimate the loop I created with the workflow ran for about 3.5 hours in total. Ouch. When I finally realised upon checking back into the channel I immediately deleted the workflow to stop the race condition, however I knew I was going to pay for my mistake.

Fast forward a day or so when I have all the billing data available. Here’s what the results of my oversight were:

Screenshot 2026-08-21 073742

The error had cost me around AU$250. D’Oh!

All of this is always a learning experience, so now that I had understood the ‘bill shock’ amount I wanted to see what more billing information I could obtain about what had actually happened. I visited the Power Platform admin center | Licensing Copilot Studio, scrolled down to Top 5 agents and users, then selected View all agents which showed me this:

image

then when I drilled into my environments I can see:

image

and at the bottom you can see the autonomous consumption of 16,376.01 credits. If I divide that by the 3.5 hour run time I get 4,678.86 credits consumed per hour. If I then divide that by 60 to get the cost per minute I get 77.98 credits. Thus, each post to the channel in effect cost around US$0.78 which is about AU$1.20.

The detail also shows that creating the agent cost around 67.26 + 379.77 = 447.37 credit which is around US$4.50 and AU$6.95 to create.

I have now added notifications at 90% capacity like so in this admin console because they are not enabled by default:

image

I would expect, like the budget notifications from Azure, they are not immediate which makes avoiding costly mistakes harder when your error maybe racking up a few dollars per minute charges!

I accept full responsibility for my error and oversight and bill incurred, however I think there are some important learnings and observations here with the new PAYG billing for AI services. These in essence boil down to the fact that it very difficult to get a good understanding of exactly what your costs are in real time or prior. Typically, you need to wait a full 24 hours until all the billing data has been collected and by then you maybe up for thousands of dollars if you are not very careful.

Another observation is that if you make a logic error in your build you won’t find that until you look at your bill. I was lucky that I found mine after a few hours, imagine if it had run for more than 24 hours before the billing data alerted me? Ouch.

I believe this lack of immediacy an d visibility on costs is going to be a major barrier for adoption of PAYG agents in Microsoft 365, whether Cowork or the new Copilot Studio, especially in SMB.

image

Hopefully, we get to a point like we have with Github Copilot (above) where I can quickly and easily see my usage in the development environment (here Visual Studio Code). Without this type of spending certainty many business are simply not going to use what are fantastic AI tools to help their business. This risk of runaway costs is simply too great.

Another point that I want to reinforce here is that when you implement PAYG with agents you need to monitor your costs DAILY! This will be a big change for many MSPs who may occasionally go into a customers tenant to look at licensing monthly. If your customer has PAYG AI and you are responsible for managing these costs you need to keep an eye on this every single day to minimise what a single logic error could cost.

Ensure you enable all the alerting that you can when you use PAYG AI services, no matter where or whom they are from. Hopefully, doing this and my sorry tale here helps you better monitor your costs and avoid ‘AI usage bill shock’.

Why AI Charges More to Write Than to Read

image

I keep seeing people look at AI pricing pages and assume someone has made a typo.

Input tokens cost one amount. Output tokens cost another. Cached input may cost less again. At first glance that feels odd. A token is a token, surely?

Not really.

The easiest way to think about it is this: reading is cheaper than writing. AI can read a lot of your prompt in parallel. It can process the instructions, pasted document, previous conversation and system rules in large chunks. That is the input side.

Writing the answer is different. The model generates the response one token at a time. Each next word, fragment, line of code or JSON field depends on what came before it. The longer the response, the longer expensive compute is tied up producing it.

That is why output tokens usually cost more. You are not just paying for text. You are paying for generation.

This matters more than most people think

Once you move into agents, automation, Copilot Studio, Azure OpenAI, GitHub Copilot, or anything that runs repeatedly, the economics change quickly.

A short prompt that produces a long report can cost more than a large prompt that produces a tiny answer. That surprises people. They assume the big document is the expensive part. Sometimes it is not. The real cost can be the polished, verbose output they asked the model to create.

Ask an AI system to read a SharePoint policy library and return three risks, and you are probably dealing with an input-heavy, output-light workload. That can be relatively efficient.

Ask it to create a 25-page report, an executive summary, a remediation plan, a Teams post, a client email and a formatted table every time it runs, and you have created an output-heavy workload. That is where the bill starts to move.

The MSP lesson is simple: design the output

This is where MSPs need to stop treating AI as magic and start treating it as infrastructure.

When we built servers, we cared about CPU, RAM, disk and backup windows. With AI, we need to care about prompts, context, output length, caching and repeatability.

The bad habit is asking for everything every time. “Give me the full report.” “Include all the detail.” “Make it comprehensive.” That sounds harmless until the same workflow runs fifty times across fifty tenants.

A better approach is to be deliberate. Ask for the smallest useful output first. Use summaries where summaries are enough. Generate detailed reports only when there is a reason. Reuse stable instructions and context where caching is available. Put spending limits around anything consumption-based. Review what the agent writes, not just what it reads.

Inside Microsoft 365, this means being clear about the difference between ordinary Copilot use in Word, Excel, Outlook or Teams and consumption-based AI work that may be billed differently. A user drafting an email is one thing. An agent chewing through documents and producing long artefacts all day is another.

This is not a pricing trick

I do not see the input/output price split as some mysterious vendor tax. It reflects how the technology behaves.

The mistake is pretending it does not matter.

AI costs are not just about how many people have a licence. They are about what those people, agents and workflows ask the model to produce. The output is where the hidden weight often sits.

So the practical rule is this: do not just prompt for the result. Design the cost shape of the result.

That might be the difference between AI being a useful business tool and AI becoming the next cloud bill nobody wants to open.

How to Configure Microsoft 365 Business Premium to Block AI Browsers: A Complete Guide to Stopping Comet and Other Agentic Browsers

Executive Summary

In December 2025, Gartner issued an urgent advisory recommending that organizations “block all AI browsers for the foreseeable future” due to critical cybersecurity risks.AI browsers like Perplexity’s Comet and OpenAI’s ChatGPT Atlas introduce threats including irreversible data loss, prompt injection vulnerabilities, and unauthorized credential access.With 27.7% of organizations already having at least one user with an AI browser installed,the time to act is now. [computerworld.com]

This comprehensive guide provides step-by-step instructions for configuring Microsoft 365 Business Premium (M365 BP), specifically Microsoft Defender for Cloud Apps, to detect, monitor, and block AI-enabled browsers like Comet from accessing your enterprise resources.


Understanding the AI Browser Threat Landscape

Why AI Browsers Are Dangerous

According to Gartner analysts, “The real issue is that the loss of sensitive data to AI services can be irreversible and untraceable. Organizations may never recover lost data.” [computerworld.com]

Key Security Concerns:

  1. Autonomous Actions Without Oversight – AI browsers can autonomously navigate websites, fill out forms, and complete transactions while authenticated, creating accountability concerns for erroneous or malicious actions [computerworld.com]
  2. Traditional Controls Are Inadequate – “Traditional controls are inadequate for the new risks introduced by AI browsers, and solutions are only beginning to emerge,” according to Gartner’s senior director analyst Evgeny Mirolyubov [computerworld.com]
  3. Multi-Modal Communication Gaps – A major gap exists in inspecting multi-modal communications with browsers, including voice commands to AI browsers [computerworld.com]
  4. Immature Security Posture – Discovered vulnerabilities highlight broader concerns about the maturity of AI browser technology, with solutions likely taking “a matter of years rather than months” to mature [computerworld.com]

Prerequisites and Licensing Requirements

Required Licenses

To implement comprehensive AI browser blocking, you need: [wolkenman….dpress.com]

License OptionWhat’s Included
Microsoft 365 Business Premium + E5 Security Add-onDefender for Cloud Apps + Defender for Endpoint
Microsoft 365 E5 / A5 / G5Full suite including Conditional Access App Control
Enterprise Mobility + Security E5Defender for Cloud Apps + Defender for Endpoint
Microsoft 365 F5 Security & ComplianceAll required components
Microsoft 365 Business Premium + Defender for Cloud Apps Add-onMinimum required configuration

Technical Prerequisites

Before implementing blocking policies, ensure: [learn.microsoft.com], [learn.microsoft.com]

  • Microsoft Defender for Cloud Apps license (standalone or bundled)
  • Microsoft Entra ID P1 license (standalone or bundled)
  • Microsoft Defender for Endpoint deployed and configured
  • Cloud Protection enabled in Defender for Endpoint [learn.microsoft.com]
  • Network Protection enabled in Defender for Endpoint [learn.microsoft.com]
  • Admin permissions – Global Administrator or Security Administrator role
  • Microsoft Defender Browser Protection extension installed on non-Edge browsers [learn.microsoft.com]

Multi-Layered Defense Strategy

Blocking AI browsers requires a comprehensive, defense-in-depth approach using multiple Microsoft 365 security layers:


Configuration Guide: Step-by-Step Implementation

Phase 1: Enable Cloud Discovery for AI Applications

Objective: Gain visibility into which AI browsers and applications are being used in your organization.

Step 1.1: Access Cloud Discovery Dashboard

  1. Navigate to Microsoft Defender Portal (https://security.microsoft.com)
  2. Go to Cloud AppsCloud DiscoveryDashboard
  3. Set the time range to Last 90 days for comprehensive analysis [wolkenman….dpress.com]

Step 1.2: Filter for Generative AI Applications

  1. In the Cloud Discovery dashboard, click Category filter
  2. Select “Generative AI” from the category list [wolkenman….dpress.com]
  3. Review discovered AI applications with their risk scores
  4. Note applications with High Risk status (red indicators) [wolkenman….dpress.com]

Step 1.3: Identify AI Model Providers and MCP Servers

Beyond browsers, also identify: [wolkenman….dpress.com]

  • AI – Model Providers (Azure OpenAI API, Google Gemini API, Anthropic Claude API)
  • AI – MCP Servers (Model Context Protocol servers)

Navigate to: Cloud AppsCloud App Catalog → Filter by “AI – Model Providers” and “AI – MCP Servers”


Phase 2: Configure Defender for Endpoint Integration

Objective: Enable automatic blocking of unsanctioned apps through network-level enforcement.

Step 2.1: Enable Enforce App Access

  1. In Microsoft Defender Portal, navigate to:
  2. Toggle “Automatically block unsanctioned apps” to ON
  3. This creates automatic indicators in Defender for Endpoint when apps are marked as unsanctioned [wolkenman….dpress.com]

Step 2.2: Verify Network Protection Status

Ensure Network Protection is enabled for all browsers: [wolkenman….dpress.com]

  1. Navigate to SettingsEndpointsConfiguration Management
  2. Go to Enforcement ScopeNetwork Protection
  3. Verify status is set to “Block mode” (not just Audit mode)
  4. Apply to All devices or specific device groups

Why This Matters: Network Protection ensures that blocks work across all browsers (Chrome, Firefox, etc.), not just Microsoft Edge. [wolkenman….dpress.com]


Phase 3: Unsanction and Block Comet Browser

Objective: Mark Comet and other AI browsers as unsanctioned to trigger automatic blocking.

Step 3.1: Search for Comet in Cloud App Catalog

  1. Go to Cloud AppsCloud App Catalog
  2. Use the search function to find “Comet” or “Perplexity”
  3. Click on the application to review its risk assessment

Note: If Comet hasn’t been discovered yet in your environment, you can still add custom URLs for blocking (see Phase 6).

Step 3.2: Unsanction the Application

  1. Click the three dots (⋮) at the end of the application row
  2. Select “Unsanctioned” [learn.microsoft.com]
  3. A confirmation dialog will appear indicating the app will be blocked by Defender for Endpoint [wolkenman….dpress.com]
  4. Click Confirm

Step 3.3: Verify Indicator Creation

  1. Navigate to SettingsEndpointsIndicatorsURLs/Domains [wolkenman….dpress.com]
  2. Confirm that domains associated with Comet appear with action “Block execution”
  3. Processing may take 5-15 minutes

Example domains that may be blocked:

  • *.perplexity.ai
  • comet.perplexity.ai
  • Related CDN and API endpoints

Phase 4: Create Conditional Access Policies

Objective: Route traffic through Defender for Cloud Apps proxy for deep inspection and control.

Step 4.1: Create Base Conditional Access Policy

  1. Sign in to Microsoft Entra Admin Center (https://entra.microsoft.com)
  2. Navigate to ProtectionConditional AccessPolicies
  3. Click + New policy [learn.microsoft.com]

Step 4.2: Configure Policy Settings

Policy Name: Block AI Browsers via Session Control

Assignments: [learn.microsoft.com]

SettingConfiguration
UsersSelect All users (exclude break-glass accounts)
Target ResourcesSelect Office 365, SharePoint Online, Exchange Online
ConditionsOptional: Add device platform, location filters

Access Controls: [learn.microsoft.com]

  • Under Session → Select “Use Conditional Access App Control”
  • Choose “Use custom policy”
  • Click Select

Enable Policy: Set to Report-only initially for testing [learn.microsoft.com]

Step 4.3: Save and Validate

  1. Click Create
  2. Wait 5-10 minutes for policy propagation
  3. Test with a pilot user account

Critical Note: Ensure the “Microsoft Defender for Cloud Apps – Session Controls” application is NOT blocked by other Conditional Access policies, or session controls will fail. [learn.microsoft.com]


Phase 5: Create Session Policies to Block AI Browser User Agents

Objective: Create real-time session policies that identify and block AI browsers based on user-agent strings and behavioral patterns.

Step 5.1: Create Access Policy for User-Agent Blocking

This is one of the most effective methods to block specific browsers like Comet. [securityhq.com]

  1. In Microsoft Defender Portal, navigate to:
  2. Click Create policyAccess policy [learn.microsoft.com]

Step 5.2: Configure Access Policy Details

Basic Information: [learn.microsoft.com]

FieldValue
Policy NameBlock AI Browsers - Comet and Similar Agents
Policy SeverityHigh
CategoryAccess control
DescriptionBlocks access attempts from AI-enabled browsers including Comet, Atlas, and other agentic browsers based on user-agent detection

Step 5.3: Set Activity Filters

Activities matching all of the following: [learn.microsoft.com]

  1. App: Select applications to protect
    • Office 365
    • Exchange Online
    • SharePoint Online
    • Microsoft Teams
    • OneDrive for Business
  2. Client app: Select Browser [learn.microsoft.com]
  3. User agent tag:
    • Contains “Comet”
    • Or create custom user-agent filter (see Step 5.4)
  4. Device type: (Optional) Apply to specific device types

Step 5.4: Create Custom User-Agent String Filters

While Defender for Cloud Apps doesn’t expose direct user-agent string matching in the UI by default, you can leverage activity filters: [securityhq.com]

Known AI Browser User-Agent Patterns to Block:

User-Agent patterns (Create separate policies or use contains logic):
- Contains "Comet"
- Contains "Perplexity"
- Contains "axios" (common in automated tools)
- Contains "ChatGPT" (for Atlas browser)
- Contains "AI-Browser"
- Contains "agentic"

Advanced Method – Using Session Policy with Inspection:

  1. Create a Session Policy instead of Access Policy
  2. Set Session control type: to “Block activities” [learn.microsoft.com]
  3. Under Activity type, select relevant activities
  4. In Inspection method, configure content inspection rules

Step 5.5: Set Actions

Actions:

  • Select “Block”
  • Enable “Notify users” with custom message:
Access Denied: AI-Enabled Browser Detected

Your organization's security policy prohibits the use of AI-enabled browsers 
(such as Comet, Atlas, or similar tools) to access corporate resources due to 
data security and compliance requirements.

Please use Microsoft Edge, Chrome, or Firefox to access this resource.

If you believe this is an error, contact your IT helpdesk.

Step 5.6: Enable Governance Actions

  • Select “Send email to user”
  • Select “Alert severity” as High
  • Enable “Create an alert for each matching event”

Step 5.7: Activate the Policy

  1. Review all settings
  2. Click Create
  3. Policy becomes active immediately
  4. Monitor via Activity Log for matches

Phase 6: Block Comet Domains via Custom Indicators

Objective: Manually add Comet-related domains to Defender for Endpoint indicators for network-level blocking.

Step 6.1: Identify Comet-Related Domains

Based on Perplexity’s infrastructure, key domains include: [computerworld.com]

Primary Domains:
- perplexity.ai
- www.perplexity.ai
- comet.perplexity.ai
- api.perplexity.ai

CDN and Supporting Infrastructure:
- *.perplexity.ai (wildcard)
- assets.perplexity.ai
- cdn.perplexity.ai

Step 6.2: Create URL/Domain Indicators

  1. Navigate to SettingsEndpointsIndicatorsURLs/Domains
  2. Click + Add item

For each domain, configure:

FieldValue
Indicatorperplexity.ai
ActionBlock
ScopeAll device groups (or specific groups)
TitleBlock Perplexity Comet Browser
DescriptionBlocks access to Perplexity Comet AI browser per organizational security policy
SeverityHigh
Generate alertYes
  1. Click Save
  2. Repeat for all identified domains

Step 6.3: Test Domain Blocking

  1. From a test device with Defender for Endpoint installed
  2. Navigate to https://www.perplexity.ai in any browser
  3. You should see: [wolkenman….dpress.com]
This site has been blocked by your organization
Microsoft Defender SmartScreen blocked this unsafe site

This web page was blocked by Microsoft Defender Application Control
perplexity.ai has been blocked by your IT administrator


Phase 7: Create Cloud Discovery Policies for Alerting

Objective: Set up automated alerts when AI browsers are detected in your environment.

Step 7.1: Create App Discovery Policy

  1. Navigate to Cloud AppsPoliciesPolicy Management
  2. Click Create policyApp discovery policy [learn.microsoft.com]

Step 7.2: Configure Discovery Policy

Policy Template: Use “New risky app” template or create custom [learn.microsoft.com]

FieldConfiguration
Policy NameAlert on New AI Browser Detection
CategoryCloud discovery
Risk scoreHigh and Medium
App categorySelect “Generative AI”
Traffic volumeGreater than 10 MB (adjust as needed)

Filters:

  • App category equals Generative AI
  • Risk score less than or equal to 6 (out of 10)
  • App tag equals Unsanctioned

Governance Actions:

  • Send email to security team
  • Create alert with High severity

Testing and Validation

Validation Checklist

Monitoring and Reporting

Activity Log Monitoring:

  1. Cloud AppsActivity Log
  2. Filter by:
    • Policy: Select your AI browser blocking policies
    • Action taken: Block
    • Date range: Last 7 days

Defender for Endpoint Alerts:

  1. Incidents & AlertsAlerts
  2. Filter by:
    • Category: Custom indicator block
    • Title: Contains “Perplexity” or “Comet”

Advanced Configuration Options

Option 1: Device Compliance Requirements

Combine AI browser blocking with device compliance:

  1. In Conditional Access policy, add ConditionsDevice platforms
  2. Require devices to be Compliant or Hybrid Azure AD Joined
  3. Use Intune compliance policies to check for:
    • Comet browser installation (custom script detection)
    • Other AI browser installations

Option 2: Warn and Educate Mode

Before full blocking, consider “Warn and Educate” mode: [learn.microsoft.com]

  1. Set indicators to “Warn” instead of “Block”
  2. Users see warning message but can proceed (with logging)
  3. Collect usage data for 2-4 weeks
  4. Transition to Block mode after user education

Option 3: Scoped Blocking by Device Groups

Target specific departments first:

  1. In Defender for Endpoint, create device groups:
    • Finance Team
    • Executive Leadership
    • High-Risk Departments
  2. Apply indicators only to these groups initially
  3. Expand gradually after validation

Option 4: DLP Integration for Data Leaving via AI Browsers

Even with blocks, ensure data leakage prevention:

  1. Create Microsoft Purview DLP policies
  2. Target “All locations” including endpoints
  3. Configure rules to detect sensitive data:
    • Credit card numbers
    • Social Security numbers
    • Confidential project names
  4. Block upload/sharing of sensitive content

Identifying Comet Browser Technical Indicators

User-Agent String Analysis

While official Comet user-agent strings aren’t publicly documented by Perplexity, AI browsers typically exhibit these patterns:

Common AI Browser User-Agent Characteristics:

Mozilla/5.0 (Platform) ... Comet/[version]
Mozilla/5.0 (Platform) ... Perplexity/[version]
Chromium-based with custom identifiers
May contain "AI", "Agent", "Agentic" in UA string

Detection Strategy:

  1. Review Activity Log in Defender for Cloud Apps
  2. Filter for unknown/suspicious user agents
  3. Export activity data with user-agent strings
  4. Analyze patterns using PowerShell or Excel
  5. Update policies based on findings

Network Traffic Patterns

Comet communicates with Perplexity cloud infrastructure: [computerworld.com]

  • High-frequency API calls to api.perplexity.ai
  • WebSocket connections for real-time AI responses
  • Upload of page content and browsing context
  • Telemetry to Perplexity servers

Monitor via Defender for Cloud Apps:

  • Cloud AppsActivity Log
  • Filter by IP address ranges (if known)
  • Look for unusual upload patterns

Troubleshooting Common Issues

Issue 1: Blocks Not Working in Chrome/Firefox

Symptom: Comet/Perplexity sites accessible in non-Edge browsers

Solution: [wolkenman….dpress.com]

  1. Verify Network Protection is enabled in Defender for Endpoint
  2. Check SettingsEndpointsConfiguration Management
  3. Ensure status is “Block” not “Audit”
  4. Restart browser and test again

Issue 2: Conditional Access Policy Not Triggering

Symptom: Users can access M365 apps without session controls

Solution:

  1. Verify Conditional Access policy is in “On” mode (not Report-only) [learn.microsoft.com]
  2. Check that “Microsoft Defender for Cloud Apps – Session Controls” app is not blocked
  3. Ensure apps are listed as “Monitored” in Conditional Access App Control [securityhq.com]
  4. Clear browser cache and test in incognito mode

Issue 3: Legitimate Traffic Being Blocked

Symptom: False positives blocking valid user activity

Solution:

  1. Review Activity Log for specific blocked events
  2. Refine user-agent filters to be more specific
  3. Create exception policies for legitimate tools
  4. Use “Exclude” filters in policies for specific users/groups

Issue 4: Indicators Not Appearing in Defender for Endpoint

Symptom: Unsanctioned apps don’t create indicators

Solution:

  1. Verify “Enforce App Access” is enabled [wolkenman….dpress.com]
  2. Check that Defender for Endpoint integration is active
  3. Wait 15-30 minutes for synchronization
  4. Manually create indicators if automatic creation fails

Best Practices and Recommendations

Strategic Recommendations

  1. Phased Rollout Approach
    • Week 1-2: Report-only mode, gather usage data
    • Week 3-4: Warn mode for user education
    • Week 5+: Full block mode enforcement
  2. User Communication Strategy[computerworld.com]
    • Send organization-wide email explaining policy
    • Provide approved alternatives
    • Create FAQ document
    • Offer training on secure browsing practices
  3. Continuous Monitoring
    • Review Cloud Discovery weekly for new AI apps
    • Monitor activity logs daily for policy violations
    • Track emerging AI browser releases
    • Update indicators quarterly
  4. Exception Process
    • Create formal request process for exceptions
    • Require executive approval for high-risk apps
    • Document business justification
    • Apply additional controls for approved exceptions (DLP, session monitoring)
  5. Defense in Depth[wolkenman….dpress.com]
    • Don’t rely solely on browser blocking
    • Implement data loss prevention (DLP)
    • Use endpoint detection and response (EDR)
    • Enable Microsoft Purview for data governance
    • Deploy insider risk management

Policy Comparison Table

MethodScopeEffectivenessUser ExperienceManagement Overhead
Cloud Discovery + UnsanctioningNetwork-wide⭐⭐⭐⭐⭐Transparent (blocked before access)Low (automated)
Session PoliciesM365 Apps only⭐⭐⭐⭐May show warning messagesMedium (requires tuning)
Access PoliciesM365 Apps only⭐⭐⭐⭐⭐Blocks before session startsMedium
Manual IndicatorsAll network traffic⭐⭐⭐⭐TransparentHigh (manual updates)
Conditional AccessCloud apps only⭐⭐⭐⭐May require re-authenticationLow

Recommended Combination: Use Cloud Discovery + Unsanctioning AND Access Policies for comprehensive coverage.


Staying Current: Monitoring New AI Browsers

AI browsers are rapidly evolving. Stay ahead of threats:

Monthly Review Checklist

Cloud App Catalog Updates

  • Review newly discovered apps in Generative AI category
  • Check for new AI Model Providers
  • Assess risk scores of emerging tools

Threat Intelligence

  • Monitor Gartner reports on AI browser security [gartner.com]
  • Follow Microsoft Security Blog
  • Subscribe to CISA alerts
  • Track CVE databases for AI browser vulnerabilities

Policy Effectiveness

  • Review blocked connection attempts
  • Analyze bypass attempts
  • Update user-agent filters
  • Refine domain lists

Emerging AI Browsers to Monitor

Beyond Comet and Atlas, watch for:

  • Brave Leo Browser (AI-enhanced features)
  • Opera One (integrated AI)
  • Arc Browser (with AI capabilities)
  • SigmaOS (AI-powered browsing)
  • Browser Company products

Compliance and Documentation

Required Documentation

Maintain these records for audit purposes:

  1. Policy Documentation
    • Policy names, purposes, and justifications
    • Configuration settings and filters
    • Approval chains and stakeholder sign-offs
  2. Change Log
    • Policy modifications
    • Domain additions/removals
    • Exception approvals
  3. Incident Reports
    • Blocked access attempts
    • Policy violations
    • User complaints and resolutions
  4. Risk Assessment
    • Why AI browsers are blocked
    • Business impact analysis
    • Alternative solutions provided to users

Regulatory Considerations

Consider these compliance frameworks:

FrameworkRelevance
GDPRData processing outside organization control
HIPAAProtected health information exfiltration risk
SOXFinancial data protection requirements
PCI DSSCardholder data security
NIST 800-53Access control requirements

Conclusion: Taking Action Against AI Browser Risks

The threat posed by AI browsers like Perplexity’s Comet is real, immediate, and growing. With security experts uniformly recommending that organizations “block all AI browsers for the foreseeable future,”the time for action is now—not later. [pcmag.com], [gartner.com]

Key Takeaways:

  1. Gartner’s Warning is Clear: AI browsers introduce “irreversible and untraceable” data loss risks that traditional controls cannot adequately mitigate [computerworld.com]
  2. Multi-Layered Defense is Essential: Combining Cloud Discovery, Session Policies, Access Policies, and Network Protection provides comprehensive coverage
  3. Microsoft 365 Business Premium Provides the Tools: With Defender for Cloud Apps and Defender for Endpoint, you have enterprise-grade capabilities to detect and block AI browsers
  4. User Education is Critical: Technical controls must be paired with clear communication about why AI browsers pose risks and what alternatives are approved
  5. Continuous Vigilance Required: The AI browser landscape evolves rapidly; monthly reviews of your defenses are essential [computerworld.com]

Immediate Action Steps

This Week:

  1. ✅ Enable Cloud Discovery and filter for Generative AI apps
  2. ✅ Review current AI browser usage in your organization
  3. ✅ Enable “Enforce App Access” in Defender for Cloud Apps
  4. ✅ Verify Network Protection is enabled in Defender for Endpoint

Next Week:

  1. ✅ Create Conditional Access policy routing traffic to MDCA
  2. ✅ Unsanction Comet and other AI browsers
  3. ✅ Create custom domain indicators for Perplexity infrastructure
  4. ✅ Deploy in Report-only mode for pilot group

Within 30 Days:

  1. ✅ Create Access Policies with user-agent filtering
  2. ✅ Enable full blocking mode organization-wide
  3. ✅ Communicate policy to all users
  4. ✅ Establish ongoing monitoring processes

Additional Resources

Microsoft Documentation:

Security Research:

Community Resources:


Step-by-Step Guide: Setting Up Entra ID Conditional Access for Small Businesses

Understanding Conditional Access

Conditional Access is Microsoft’s Zero Trust policy engine that evaluates signals from users, devices, and locations to make automated access decisions and enforce organizational policies. Think of it as intelligent “if-then” statements: If a user wants to access a resource, then they must complete an action (like multifactor authentication).

For SMBs using Microsoft 365 Business Premium, Conditional Access provides enterprise-grade security without requiring complex infrastructure, protecting your organization from 99.9% of identity-based attacks.

Prerequisites

  • License Requirements: Microsoft 365 Business Premium (includes Entra ID P1) or Microsoft 365 E3/E5
  • Admin Role: Conditional Access Administrator or Global Administrator privileges
  • Preparation: Ensure all users have registered for MFA before implementing policies
  • Emergency Access Account: Create at least one break-glass account excluded from all policies

Phase 1: Initial Setup and Planning (Week 1)

Step 1: Turn Off Security Defaults

  1. Navigate to Microsoft Entra admin center (entra.microsoft.com)
  2. Go to Entra IDProperties
  3. Select Manage security defaults
  4. Toggle Security defaults to Disabled
  5. Select My organization is using Conditional Access as the reason
  6. Click Save

Important: Only disable security defaults after you’re ready to create Conditional Access policies immediately.

Step 2: Create Emergency Access Accounts

  1. Create two cloud-only accounts with complex passwords
  2. Assign Global Administrator role to both accounts
  3. Store credentials securely (separate locations)
  4. Document these accounts for emergency use only
  5. Exclude these accounts from ALL Conditional Access policies

Step 3: Access the Conditional Access Portal

  1. Sign in to entra.microsoft.com
  2. Navigate to Entra IDConditional Access
  3. Select Policies to view the main dashboard

Phase 2: Create Baseline Policies (Week 1-2)

Policy 1: Require MFA for All Users

  1. Click New policy from templates
  2. Select Require multifactor authentication for all users template
  3. Name your policy: “Baseline: MFA for All Users”
  4. Under Assignments:
    • Users: All users
    • Exclude: Select your emergency access accounts
  5. Under Target resources:
    • Select All resources (formerly ‘All cloud apps’)
  6. Under Access controlsGrant:
    • Select Require multifactor authentication
  7. Set Enable policy to Report-only
  8. Click Create

Policy 2: Block Legacy Authentication

  1. Click New policy from templates
  2. Select Block legacy authentication template
  3. Name your policy: “Security: Block Legacy Authentication”
  4. Under Assignments:
    • Users: All users
    • Exclude: Emergency access accounts
  5. Under ConditionsClient apps:
    • Configure: Yes
    • Select Exchange ActiveSync clients and Other clients
  6. Under Access controlsGrant:
    • Select Block access
  7. Set Enable policy to Report-only
  8. Click Create

Policy 3: Require MFA for Administrators

  1. Click New policy from templates
  2. Select Require multifactor authentication for admins template
  3. Name your policy: “Security: MFA for Admin Roles”
  4. Under Assignments:
    • Users: Select users and groups
    • Select Directory roles
    • Choose all administrative roles
    • Exclude: Emergency access accounts
  5. Under Access controlsGrant:
    • Select Require multifactor authentication
  6. Set Enable policy to Report-only
  7. Click Create

Phase 3: Testing and Validation (Week 2)

Step 1: Use the What If Tool

  1. Navigate to Conditional AccessPoliciesWhat If
  2. Enter test scenarios:
    • Select a test user
    • Choose target applications
    • Set device platform and location
  3. Click What If to see which policies would apply
  4. Review both “Policies that will apply” and “Policies that will not apply”
  5. Document results for each test scenario

Step 2: Monitor Report-Only Mode

  1. Leave policies in Report-only mode for at least 7 days
  2. Navigate to Entra IDSign-in logs
  3. Filter by Conditional Access = Report-only
  4. Review impacts:
    • Check for “Report-only: Success” entries
    • Investigate any “Report-only: Failure” entries
    • Look for “Report-only: User action required” entries
  5. Address any issues before enforcement

Step 3: Pilot Testing

  1. Create a pilot group with 5-10 users
  2. Create a duplicate policy targeting only the pilot group
  3. Set this pilot policy to On (enforced)
  4. Monitor for 3-5 days
  5. Gather feedback from pilot users
  6. Address any issues identified

Phase 4: Production Deployment (Week 3)

Step 1: Enable Policies

  1. After successful testing, return to each policy
  2. Change Enable policy from Report-only to On
  3. Start with one policy at a time
  4. Wait 2-4 hours between enabling each policy
  5. Monitor sign-in logs after each activation

Step 2: Communicate to Users

  1. Send announcement email before enforcement
  2. Include:
    • What’s changing and when
    • Why it’s important for security
    • What users need to do (register for MFA)
    • Support contact information
  3. Provide MFA registration instructions
  4. Schedule optional training sessions

Phase 5: Advanced Policies (Week 4+)

Optional: Require Compliant Devices

Only implement after basic policies are stable

  1. Create new policy: “Security: Require Compliant Devices”
  2. Target high-value applications first
  3. Under Grant controls:
    • Select Require device to be marked as compliant
  4. Test thoroughly before enforcement

Optional: Location-Based Access

  1. Define trusted locations (office IP addresses)
  2. Create policies based on location:
    • Block access from specific countries
    • Require MFA when not in trusted location

Troubleshooting Common Issues

Users Can’t Sign In

  • Check sign-in logs for specific error messages
  • Use What If tool to identify blocking policies
  • Verify user has completed MFA registration
  • Temporarily exclude user while investigating

Policy Not Applying

  • Verify policy is set to “On” not “Report-only”
  • Check assignment conditions match user scenario
  • Review excluded users and groups
  • Wait 1-2 hours for policy propagation

Emergency Rollback

  1. Navigate to problematic policy
  2. Set Enable policy to Off
  3. Or exclude affected users temporarily
  4. Document issue for resolution
  5. Re-enable after fixing configuration

Training Resources

Microsoft Learn Modules (Free)

Documentation and Guides

Video Resources

Best Practices Summary

  • ✅ Always maintain emergency access accounts excluded from all policies
  • ✅ Test every policy in Report-only mode for at least 7 days
  • ✅ Use the What If tool before and after creating policies
  • ✅ Start with Microsoft’s template policies – they represent best practices
  • ✅ Document all policies and their business justification
  • ✅ Monitor sign-in logs regularly for anomalies
  • ✅ Communicate changes to users before enforcement
  • ✅ Have a rollback plan for every policy
  • ✅ Implement policies gradually, not all at once
  • ✅ Review and update policies quarterly

CIA Brief – 231111

How AI Can Improve Threat Intelligence Gathering and Usage – https://techcommunity.microsoft.com/t5/educator-developer-blog/how-ai-can-improve-threat-intelligence-gathering-and-usage/ba-p/3975449

Reflecting on 20 years of Windows Patch Tuesday – https://blogs.windows.com/windowsexperience/2023/11/09/reflecting-on-20-years-of-windows-patch-tuesday/

Must-have skills for the AI era | AI at work with Microsoft’s Jared Spataro – https://www.youtube.com/watch?v=F8nzcGC8la0

Using Microsoft Defender Threat Intelligence with the Diamond Model for Threat Intelligence – https://techcommunity.microsoft.com/t5/microsoft-defender-threat/using-microsoft-defender-threat-intelligence-with-the-diamond/ba-p/3976100

Insights from Microsoft Security Copilot early adopters – https://www.microsoft.com/en-us/security/blog/2023/11/08/insights-from-microsoft-security-copilot-early-adopters/

Microsoft shares threat intelligence at CYBERWARCON 2023 – https://www.microsoft.com/en-us/security/blog/2023/11/09/microsoft-shares-threat-intelligence-at-cyberwarcon-2023/

Copilot in Microsoft 365 Chat | Uncover Similar Themes – https://www.youtube.com/watch?v=Hj5xpC5_ZJw

Create a company-wide signature or disclaimer in Microsoft 365 – https://www.youtube.com/watch?v=r-JDQPeoLig

Microsoft 365 Chat | Generate New Ideas with Copilot – https://www.youtube.com/watch?v=tU96RtPhQ0k

Microsoft 365 Chat | Manage Your Inbox – https://www.youtube.com/watch?v=yWC2XcRvH7E

Copilot in Teams | Get meeting overviews – https://www.youtube.com/watch?v=UNQeA2uqNPA

Now is the time—manage your Mac endpoints with Microsoft Intune – https://techcommunity.microsoft.com/t5/microsoft-intune-blog/now-is-the-time-manage-your-mac-endpoints-with-microsoft-intune/ba-p/3974449

Simplified security settings management is now generally available – https://techcommunity.microsoft.com/t5/microsoft-defender-for-endpoint/simplified-security-settings-management-is-now-generally/ba-p/3975158

Getting started with Microsoft Lists – Edit a view of a list – https://www.youtube.com/watch?v=Xcd7IW3p8Fw

Copilot in Microsoft 365 Chat | Grow your knowledge – https://www.youtube.com/watch?v=hkS-qS0ClSs

Discover, prepare, and recap your meetings in one place with Meet in Microsoft Teams – https://www.youtube.com/watch?v=JBxI4qiBPdk

Getting started with OneDrive – Share files and folders with Microsoft 365 – https://www.youtube.com/watch?v=Rs7hqD8nzyw

Emphasizing Security by Default with Advanced Microsoft Authenticator Features. – https://techcommunity.microsoft.com/t5/microsoft-entra-azure-ad-blog/emphasizing-security-by-default-with-advanced-microsoft/ba-p/3773130

Automatic Conditional Access policies in Microsoft Entra streamline identity protection – https://www.microsoft.com/en-us/security/blog/2023/11/06/automatic-conditional-access-policies-in-microsoft-entra-streamline-identity-protection/

Enterprise IoT security with Defender for IoT now included in Microsoft 365 E5 and E5 Security plans – https://techcommunity.microsoft.com/t5/microsoft-365-defender-blog/enterprise-iot-security-with-defender-for-iot-now-included-in/ba-p/3967533

What’s new for Security: Training and Certification – https://techcommunity.microsoft.com/t5/microsoft-learn-blog/what-s-new-for-security-training-and-certification/ba-p/3644507

Complete the new 30 Days to Learn It Challenge and explore the new trainings in Security – https://techcommunity.microsoft.com/t5/security-compliance-and-identity/complete-the-new-30-days-to-learn-it-challenge-and-explore-the/ba-p/3966324

Copilot in Outlook | Manage your inbox – https://www.youtube.com/watch?v=PSTSOyBccnY

Copilot in Word | Locate key information – https://www.youtube.com/watch?v=hxc5t3AfpKo

Copilot in Word | Transform a document – https://www.youtube.com/watch?v=Tx0IbvgI4NA

Announcing Microsoft Secure Future Initiative to advance security engineering – https://www.microsoft.com/en-us/security/blog/2023/11/02/announcing-microsoft-secure-future-initiative-to-advance-security-engineering/

After hours

Candy Thieves vs Rigged Candy Bowl – https://www.youtube.com/watch?v=Zb01RStdzEs

Editorial

Next week is going to be a firehose with Microsoft Ignite taking place, so be prepared for lots of links in the CIA Brief next week.

If you found this valuable, the I’d appreciate a ‘like’. This helps me know that people enjoy what I have created. If you have any feedback or suggestions around this, I’m all ears. You can also find me via email director@ciaops.com and on X (Twitter) at https://www.twitter.com/directorcia.

Watch out for the next CIA Brief next week.

Need to Know podcast–Episode 300

In this episode I cover off why adding Azure to every environment makes sense. Even though the billing model is different that doesn’t there isn’t an opportunity to add value to an environment with what Azure can provide. There are also plenty of updates from the Microsoft Cloud with many exciting new things to try. Listen along and let me know if you have any feedback.

You can listen directly to this episode at:

https://ciaops.podbean.com/e/episode-300-why-you-should-add-azure/

Subscribe via iTunes at:

https://itunes.apple.com/au/podcast/ciaops-need-to-know-podcasts/id406891445?mt=2

The podcast is also available on Stitcher at:

http://www.stitcher.com/podcast/ciaops/need-to-know-podcast?refid=stpr

Don’t forget to give the show a rating as well as send me any feedback or suggestions you may have for the show

This episode was recorded using Microsoft Teams and produced with Camtasia 2022.

Brought to you by www.ciaopspatron.com

Resources

@directorcia

@directorcia@twit.social

Join my shared channel

CIAOPS merch store

Become a CIAOPS Patron

CIAOPS Blog

YouTube edition of this podcast

Introducing the new Microsoft Teams, now in preview

The new Teams

Welcome to the new era of Microsoft Teams

Windows 365 Frontline available in public preview

Adding your Microsoft Store for Business and Education apps to the Microsoft Store in Intune

What’s New at Microsoft Secure

Avatars for Microsoft Teams

Introducing Microsoft Security Copilot: Empowering defenders at the speed of AI

Explaining the Microsoft 365 Copilot System

Microsoft Incident Response Retainer is generally available

Microsoft awarded Best Advanced Protection for Corporate and Consumer Users by AV-TEST

New Microsoft Intune Devices experience

What’s new in Microsoft Intune – 2303 (March) edition

How to enable Microsoft Authenticator Lite for Outlook mobile (preview)

Need to Know podcast–Episode 285

I’m back baby! It’s been quite a while now but I’ve decided to start getting the Microsoft Cloud information and updates out there irrespectively of whether there is a guest or not. Let’s see how that goes and please let me know what you think and any suggestions you may have.

I’ll also bring you up to date with all the latest news from the Microsoft Cloud.

Take a listen and let us know what you think – director@ciaops.com

You can listen directly to this episode at:

https://ciaops.podbean.com/e/episode-285-updates/

Subscribe via iTunes at:

https://itunes.apple.com/au/podcast/ciaops-need-to-know-podcasts/id406891445?mt=2

The podcast is also available on Stitcher at:

http://www.stitcher.com/podcast/ciaops/need-to-know-podcast?refid=stpr

Don’t forget to give the show a rating as well as send me any feedback or suggestions you may have for the show.

This episode was recorded using Microsoft Teams and produced with Camtasia 2022.

Brought to you by www.ciaopspatron.com

Resources

@directorcia

Basic Authentication Deprecation in Exchange Online – September 2022 Update

Stream mobile app in beta

Microsoft to drop Kaizala in 2023

Microsoft Security highlights from Black Hat USA 2022

What’s new in Microsoft Endpoint Manager – 2208 (August) edition

Microsoft Defender monthly news August

Enabling corporate access using browser controls in Windows

Microsoft Entra Verified ID now generally available

Microsoft announces new solutions for threat intelligence and attack surface management

Microsoft Ignite

CIAOPS Shared channel

CIAOPS Need to Know webinar September