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Enterprise AI

Shadow AI in the Enterprise: How to Detect and Manage Unapproved AI Usage

Feb 17, 2026

StackAI

AI Agents for the Enterprise

StackAI

AI Agents for the Enterprise

Shadow AI in the Enterprise: How to Detect It

Shadow AI in the enterprise isn’t a future problem. It’s already happening in most organizations, quietly and at scale. An employee pastes sensitive customer details into a public chatbot to draft an email. A team enables an “AI meeting notes” app with broad access to calendars and files. A developer slips an unapproved model API into production code to speed up a feature.


None of these are malicious. That’s the point. Shadow AI in the enterprise spreads because it works, it’s easy, and it feels harmless. But without visibility and controls, it becomes a data movement problem that can trigger internal data exposure, compliance breakdowns, and painful rework.


This guide breaks down what shadow AI in the enterprise is, why it’s spreading, the real risk landscape, and a practical, multi-signal approach to shadow AI detection that security and IT teams can implement without grinding productivity to a halt.


What “Shadow AI” Means (and Why It’s Different from Shadow IT)

Definition (simple + enterprise-specific)

Shadow AI in the enterprise is the use of AI tools, models, or AI-driven workflows without formal approval, oversight, or controls.


That can include:

  • Employees pasting sensitive text into public AI chat tools

  • Unapproved AI browser extensions that can read page content

  • “Free” AI writing or PDF tools used for customer or regulated documents

  • OAuth-based AI apps granted access to Drive, SharePoint, email, CRM, or calendars

  • Unsanctioned model APIs embedded into internal code or automations


The defining trait isn’t the tool. It’s the lack of governance: no review, no auditing, no clear data rules, and no way to prove what happened after the fact.


Shadow AI vs. Shadow IT vs. “Bring Your Own Model” (BYOM)

Shadow AI in the enterprise overlaps with shadow IT, but it introduces risk types that traditional shadow IT programs weren’t built to handle.


Here’s the practical difference:

  • Shadow IT: unapproved software or services used to get work done (file sharing apps, project tools, unsanctioned SaaS)

  • Shadow AI in the enterprise: unapproved AI usage where sensitive data can be copied, uploaded, transformed, summarized, or routed through third-party models

  • BYOM: teams using their own chosen foundation models (or open-source models) in workflows without standard evaluation, logging, or access controls


AI raises the stakes because:

  • Prompts and uploads may contain sensitive data and secrets

  • Outputs can be wrong, biased, or leak information across contexts

  • Data handling and retention can be opaque

  • Embedded copilots and plugins can quietly expand access to enterprise systems

  • Model routing can shift where data is processed without teams realizing it


If shadow IT was an app sprawl problem, shadow AI in the enterprise is a data and decision sprawl problem.


Why Shadow AI Is Spreading in Enterprises

Shadow AI in the enterprise typically isn’t driven by rebellion. It’s driven by incentives and friction.


Common root causes include:


AI features are embedded in everyday tools


Employees don’t “adopt an AI tool” anymore. AI shows up inside email, docs, CRM, ticketing systems, call center platforms, and browser experiences. Usage accelerates before governance teams even know what to ask.


Pressure to move faster


Sales wants faster prospect research. Support wants faster replies. Legal wants faster reviews. Engineering wants faster coding. When timelines compress, employees reach for whatever removes friction.


Lack of sanctioned alternatives


If approved tools are slow to procure, hard to access, or too limited, teams fill the gap. Most shadow AI in the enterprise is “work avoidance avoidance”: people trying to avoid manual work.


Confusing policies and inconsistent enforcement


When policies say “don’t use AI” but leaders celebrate AI productivity wins, employees make their own interpretation. If enforcement varies by department, shadow usage becomes normalized.


Procurement friction vs. “just use the free version”


A $20/month subscription can bypass governance instantly. Corporate cards, browser extensions, and freemium SaaS make it easy to start and hard to see.


A governance paper on enterprise AI agents frames the core organizational failure mode well: adoption doesn’t collapse because teams can’t build AI. It collapses when controls don’t keep pace, leading to shadow tools, blanket bans, and audit questions no one can answer.


The Risk Landscape: What Shadow AI Can Break

Shadow AI in the enterprise isn’t one risk. It’s several risk classes that compound.


Data exposure and leakage

This is the most immediate issue, and it happens through more paths than copy/paste.


High-risk mechanisms include:

  • Copy/paste of sensitive text into chat interfaces

  • File uploads (contracts, spreadsheets, customer lists, claim documents)

  • Connectors and plugins pulling data from Drive/SharePoint/CRM

  • “AI assistants” embedded in browsers capturing page content

  • Meeting note tools ingesting calls that include regulated data


Data types commonly involved:

  • PII/PHI

  • Customer data and financial data

  • Source code and proprietary logic

  • Credentials, tokens, and secrets

  • M&A or strategic documents


Compliance and legal

Shadow AI in the enterprise can create compliance exposure even if the output is accurate.


Where it breaks down:

  • GDPR/CCPA and consent limitations on processing

  • HIPAA implications if PHI is handled by unapproved vendors

  • PCI scope creep if payment data is processed outside controls

  • Data residency and cross-border processing surprises

  • Records retention and eDiscovery gaps when prompts and outputs aren’t captured


IP and competitive risk

Two common IP failure modes:

  • Sensitive product details or strategy are used in prompts

  • Generated outputs are used externally without proper review, creating accidental disclosure or misrepresentation


Even when vendors claim they don’t train on customer data, enterprises still need enforceable controls: what can be submitted, how long data is retained, who can access it, and whether any part of the workflow is routed elsewhere.


Security and supply chain

Shadow AI in the enterprise expands your attack surface:

  • Malicious extensions that read pages, capture inputs, or inject content

  • OAuth apps requesting broad permissions (“read all files,” “access mail,” “offline access”)

  • Prompt injection and data exfil paths in AI-enabled workflows

  • Compromised SaaS accounts used to access AI tools and connected data

  • Unvetted model endpoints and exposed API keys in code repositories


Cost and sprawl

The hidden cost isn’t only subscription spend. It’s duplication and unmanaged usage.


Symptoms include:

  • Multiple departments paying for overlapping tools

  • Unknown token usage and unpredictable variable costs

  • Shadow workflows that become business-critical with no owner, no SLA, and no support path


What to Look For: Common Shadow AI Patterns (Detection Use Cases)

Shadow AI detection works best when you’re hunting patterns, not brands. Tools change quickly, but behaviors and access paths are consistent.


User behavior patterns

Look for:

  • Frequent visits to AI chat sites during working hours

  • Large clipboard events followed by outbound web submissions

  • Repeated uploads of documents to web apps

  • Rapid “draft and send” patterns where outputs are being used externally without review

  • Usage spikes after policy announcements (a sign of pushback or confusion)


SaaS and app patterns

Look for:

  • New AI SaaS sign-ups using corporate email domains

  • New OAuth consent grants to unknown apps

  • AI apps with read/write permissions to Drive/SharePoint/Box

  • Plugins or add-ons installed inside approved SaaS platforms

  • Embedded AI features toggled on by end users without central config


Developer and API patterns

Look for:

  • New outbound calls to model API endpoints from internal services

  • Prompt logging disabled or absent entirely

  • API keys committed to repos, ticket comments, or build logs

  • Open-source model pulls into environments without review of licensing and security posture

  • New egress routes from cloud workloads to third-party inference services


Examples by category (so you know what “counts”)

Without turning your program into a never-ending vendor list, these categories are common sources of shadow AI in the enterprise:

  • Public chat assistants and “research” chat tools

  • AI writing and rewriting tools inside browsers

  • Meeting transcription and note summarization tools

  • AI PDF tools used for summarizing, extracting, or rewriting documents

  • Code assistants and agentic dev tools using external model endpoints

  • Email assistants and outbound messaging generators

  • AI customer support plugins connected to ticketing systems

  • Sales enablement AI connected to CRM and email


How to Detect Shadow AI: A Practical, Multi-Signal Approach

Shadow AI in the enterprise is rarely visible from a single lens. The most reliable approach correlates signals across network, identity, endpoint, and data controls.


Start with an inventory baseline (what’s approved)

Before you detect what’s unauthorized, define what’s authorized.


Build a “sanctioned AI catalog” that includes:

  • Approved tools and approved models

  • Approved use cases by department

  • Data allowed and data prohibited (by classification)

  • Approved connectors (Drive/SharePoint/CRM) and permission scope boundaries

  • Logging and retention expectations


Also define restricted data classes clearly:

  • Customer PII/PHI

  • Financial account information

  • Source code, secrets, keys, credentials

  • Board materials, M&A, strategic roadmaps

  • HR and employee data


This baseline turns detection into a simple question: “Is this data flow allowed by policy and controls?”


Network and DNS signals (web traffic discovery)

Network telemetry is often the fastest path to initial visibility.


Focus on:

  • DNS queries to AI domains and model API endpoints

  • Proxy/SWG/SASE logs showing AI tool usage

  • Upload events to AI services (multipart form uploads, large POST bodies)

  • Category-based filtering for “AI and machine learning” web services


Practical tips:

  • Don’t rely on a static domain list alone. AI endpoints change frequently.

  • Segment by risk: chat tools, file upload tools, OAuth tools, developer API endpoints.

  • Track trends over time by user, department, and location.


CASB and SaaS discovery signals

CASB-style discovery helps you find what users adopted with corporate identities or sanctioned browsers.


What to monitor:

  • Unsanctioned AI SaaS discovered through app catalogs

  • Newly observed AI apps with corporate email sign-ups

  • Risk scoring based on vendor posture (security controls, privacy, compliance artifacts)

  • Shadow SaaS that suddenly appears and gains adoption quickly


This is where you often uncover the “quietly embedded” shadow AI in the enterprise: AI features inside tools that were approved for non-AI usage.


Identity signals (SSO, OAuth, MFA, access patterns)

Identity is one of the cleanest detection surfaces because it captures the moment a user grants access.


Look for:

  • New “Sign in with Google/Microsoft” usage for AI apps

  • OAuth consent grants, especially with high-risk scopes

  • “Offline access” requests that persist beyond user sessions

  • Apps requesting broad file permissions and mailbox access

  • Anomalies like impossible travel or suspicious logins tied to AI SaaS accounts


Controls that reduce risk without heavy blocking:

  • Conditional access policies for unknown apps

  • Requiring admin consent for high-risk OAuth scopes

  • MFA enforcement and session controls for AI-related apps


Endpoint signals (extensions, local apps, clipboard behaviors)

Shadow AI in the enterprise often arrives as a browser extension or lightweight desktop app.


Monitor for:

  • New browser extensions with permissions to read page content or all sites

  • Local “AI assistant” apps installed outside managed software channels

  • Local model runners and CLI tools used to download models and weights

  • EDR telemetry on suspicious processes and browser injection behavior

  • Software inventory deltas after major AI news cycles or internal policy changes


Even basic extension governance can eliminate a major portion of shadow AI risk quickly.


DLP and data classification signals

DLP is where you catch the moment sensitive data tries to leave.


High-value detections:

  • Copy/paste of classified text into web forms

  • Upload of labeled documents to unapproved domains

  • Outbound traffic containing patterns like SSNs, account numbers, health identifiers

  • Source code and secrets leaving through browser submissions or API calls


For best results:

  • Pair DLP with data labeling (confidential, customer, regulated, source code)

  • Tune alerts by severity and destination category (not every AI tool is equal risk)

  • Build an exception path so teams don’t create workarounds


Email and procurement signals

Shadow AI detection isn’t only technical. Finance and procurement signals often reveal what security tools miss.


Look for:

  • Expense reports with AI vendor names

  • Corporate card subscriptions that bypass procurement

  • Invoices in AP systems for niche AI tools

  • Vendor intake forms submitted by teams who already adopted a tool


A simple process improvement: make “AI tool request” a fast lane, not a dead end. If the approved path is faster than the shadow path, usage shifts naturally.


Developer tooling signals (code and cloud)

Developer-driven shadow AI in the enterprise is a high-impact category because it can reach production systems quickly.


Monitor for:

  • Secrets scanning in Git repos to detect model API keys

  • New dependencies or SDKs for model providers

  • Egress monitoring from cloud workloads to model endpoints

  • Unexpected cost spikes tied to token usage

  • Containers pulling model weights from unapproved registries


Treat this like any other third-party service integration: it needs review, logging, and ownership.


Shadow AI detection checklist (10 steps)

  1. Define a sanctioned AI catalog (tools, models, use cases, data rules).

  2. Classify restricted data types and label what matters.

  3. Turn on SWG/SASE/proxy logging for AI category discovery.

  4. Monitor DNS queries and outbound egress to common model endpoints.

  5. Enable SaaS discovery to find new AI applications by usage patterns.

  6. Audit OAuth consents and flag high-risk scopes automatically.

  7. Enforce conditional access and admin consent where appropriate.

  8. Govern browser extensions and collect endpoint software inventory deltas.

  9. Tune DLP for copy/paste and uploads to unapproved AI destinations.

  10. Add procurement and repo scanning to catch spend and embedded APIs.


A Step-by-Step Shadow AI Detection Program (30–60–90 Days)

Shadow AI in the enterprise doesn’t disappear because you found it once. You need a program that creates sustained visibility and reduces incentives for unsafe workarounds.


First 30 days (visibility and quick wins)

Focus: get a real baseline and reduce obvious high-risk behaviors.


Actions:

  • Publish a clear “safe use” policy that employees can follow, not a blanket ban

  • Stand up the sanctioned AI catalog, even if it starts small

  • Turn on logging across SWG/SASE, CASB discovery, and SSO app inventory

  • Identify top AI destinations and categorize them by risk

  • Block or restrict the highest-risk behaviors first (for example: uploads of labeled sensitive documents to unapproved sites)

  • Start monitoring OAuth grants and create a rapid revoke process


Deliverable: a short report showing what shadow AI in the enterprise exists today, by department and risk category.


Days 31–60 (controls and workflows)

Focus: build repeatable workflows so detection leads to action.


Actions:

  • Tune DLP rules based on real alerts, not guesses

  • Expand labeling adoption for the datasets that matter most

  • Create a formal AI intake workflow for tools and use cases, with clear SLAs

  • Establish an exception process so teams can move quickly when needed

  • Train SOC/helpdesk on AI-related triage: OAuth revocation, extension removal, key rotation, and user coaching


Deliverable: a working detection-to-remediation workflow with owners and playbooks.


Days 61–90 (governance and continuous monitoring)

Focus: shift from “project mode” to “operating mode.”


Actions:

  • Implement quarterly app review for AI vendors and embedded AI features

  • Integrate AI tools into third-party risk management (TPRM) processes

  • Build an executive dashboard with adoption and risk metrics

  • Run red-team exercises: prompt injection drills, data exfil simulations, OAuth abuse scenarios

  • Standardize approvals, publishing controls, and auditability for enterprise AI agents


Deliverable: a governance rhythm that keeps shadow AI in the enterprise from reappearing every quarter.


Metrics and Dashboards: How to Prove You’re Reducing Shadow AI

Executives will ask two questions: “Are we safer?” and “Are people still productive?” Your metrics should answer both.


High-signal KPIs:

  • Number of unsanctioned AI apps discovered (trend over time)

  • Percentage of AI usage routed through approved tools

  • DLP incidents related to AI (volume and severity)

  • Number of risky OAuth grants detected and remediated

  • Mean time to detect (MTTD) shadow AI in the enterprise

  • Mean time to remediate (MTTR) and close out exceptions

  • Extension install rate for AI-related extensions on managed endpoints

  • Training completion and policy acknowledgment rates by department


A simple dashboard layout:

  • Discovery: new apps, new domains, new OAuth grants

  • Risk: incidents by severity and data type

  • Control coverage: percent of users/dev teams under key controls

  • Adoption: usage of sanctioned AI tools vs. unsanctioned alternatives

  • Remediation: time-to-close and repeat offender patterns


Policy and Enablement: Reducing Shadow AI Without Killing Productivity

The fastest way to grow shadow AI in the enterprise is to overblock without offering a safe path forward. People still have deadlines.


Write a clear AI acceptable use policy

Good policies are concrete. They avoid vague language like “don’t input sensitive data” without defining sensitive data.


Include:

  • Data that is never allowed in prompts or uploads (PII/PHI, secrets, credentials, unreleased financials)

  • Approved tools list and what each tool is for

  • A request path with turnaround expectations

  • Rules for verifying outputs before they are used externally

  • Guidance for storing prompts/outputs when records retention matters


Provide safe alternatives (the biggest adoption lever)

If you want less shadow AI in the enterprise, offer an enterprise-ready alternative that aligns with how teams actually work.


Teams typically need:

  • Approved models and tools with clear data handling commitments

  • Secure integrations to internal systems (SharePoint, Drive, CRM, ticketing)

  • Oversight features, including review steps for high-impact outputs

  • Access controls and SSO-based authentication

  • Logging and observability for auditability


For enterprise AI agents specifically, the difference between trusted automation and chaos is governance: access controls, publishing controls, and audit trails. Platforms built for enterprise deployment often include role-based access control, SSO integration, and restrictions so only reviewed agents can be published, along with monitoring and traceability for accountability.


Training that matches reality

Training should be role-based, not generic.


Examples that resonate:

  • Marketing: “Never upload customer lists for segmentation; use approved enrichment workflows.”

  • Sales: “Don’t paste deal notes with identifiable customer data into public chat tools.”

  • Engineering: “Never commit model API keys; use approved secrets management and approved model endpoints.”

  • Legal/HR: “Treat employee and contract data as restricted; use sanctioned tools with retention controls.”


Governance model

Shadow AI in the enterprise becomes manageable when there’s a clear owner and decision path.


A lightweight model that works:

  • AI steering committee (Security, IT, Legal, Compliance, Data)

  • Tool evaluation rubric: security posture, privacy terms, retention, residency, access scope, logging

  • Standard approval gates for connectors and OAuth permissions

  • Ongoing review of embedded AI features in existing SaaS


Common Pitfalls When Detecting Shadow AI (and How to Avoid Them)

Relying on a single signal


Web logs alone won’t catch OAuth-driven access or embedded AI features. Identity alone won’t catch copy/paste into public tools. Use a multi-signal approach.


Overblocking leading to workarounds


If you block everything, users switch to personal devices and networks. Start with high-risk behaviors, not broad categories.


Ignoring embedded AI inside approved SaaS tools


Shadow AI in the enterprise frequently shows up as a new AI feature in a tool that’s already approved. Your program must monitor feature enablement and connectors, not only new apps.


Overlooking plugins, connectors, and OAuth scopes


OAuth is one of the fastest ways to accidentally grant broad access. Monitor and constrain it aggressively.


Not maintaining domain and endpoint intelligence


AI providers change endpoints, and new tools appear constantly. Your detection process must be ongoing, not one-time.


No exception process


If there’s no path to approval, teams will build underground. Exceptions should be documented, time-bound, and measurable.


Treating all AI as equal risk


Risk depends on data, permissions, and workflow. Segment by:

  • Data sensitivity

  • Access scope (OAuth permissions)

  • Persistence (offline access, retention)

  • Business impact of wrong outputs


Shadow AI Incident Response: What to Do When You Find It

Finding shadow AI in the enterprise is inevitable. The question is how fast you can contain and learn.


A practical incident response flow:


11.

Triage severity

Determine data involved (PII/PHI/IP/secrets), how many users, and whether the tool had connectors into enterprise systems.



12. Contain quickly


  1. Revoke OAuth tokens and app grants

  2. Disable or remove extensions

  3. Disable accounts if compromise is suspected

  4. Rotate exposed keys and secrets immediately

  5. Preserve logs and evidence

    Pull relevant identity logs, proxy logs, endpoint telemetry, and DLP events. You need a defensible timeline.

  6. Remediate and prevent recurrence

    Decide whether to onboard the tool (with controls) or block it. Coach the user, but also fix the incentive that drove the behavior.

  7. Notify and report when required

    Use defined criteria for legal/compliance notifications, especially when regulated data may have been involved.


Done well, incident response becomes a discovery engine: every incident tightens your catalog, controls, and training.


Conclusion: Build Visibility First, Then Governance

Shadow AI in the enterprise is not a fringe problem and it’s not solved by policy alone. It’s solved by visibility across network, identity, endpoint, and data controls, paired with a sanctioned path that helps teams move fast safely.


Start by detecting what’s already happening. Then reduce risk with targeted controls, better oversight, and approved alternatives that people actually want to use. That’s how you shrink shadow AI in the enterprise without shrinking productivity.


Book a StackAI demo: https://www.stack-ai.com/demo

StackAI

AI Agents for the Enterprise


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