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Investigating alerts for impossible travel or anomalous token usage in Microsoft Entra ID
Responding to a suspected session hijacking or pass-the-cookie attack
Configuring proactive defenses against OAuth token theft in an Azure/M365 environment
Detecting OAuth device code phishing campaigns that bypass MFA
Analyzing sign-in logs for token replay indicators
Implementing Token Protection conditional access policies to bind tokens to devices
Do not use for on-premises Kerberos ticket attacks (pass-the-ticket, golden ticket); use Active Directory-specific investigation techniques for those scenarios.
Prerequisites
Microsoft Entra ID P2 license (required for Identity Protection risk detections and conditional access)
Global Administrator or Security Administrator role in the Entra admin center
Microsoft Defender for Cloud Apps (MDCA) license for session anomaly detection
Access to Entra ID Sign-in Logs and Audit Logs (requires Diagnostic Settings configured to Log Analytics or Sentinel)
Microsoft Sentinel or equivalent SIEM ingesting Entra ID sign-in and audit logs
Workflow
Step 1: Understand the Token Theft Attack Surface
Identify which token types are at risk and how they are stolen:
Token Type | Lifetime | Theft Vector | Impact
----------------------|-------------|----------------------------------|------------------
Access Token | 60-90 min | Memory dump, proxy interception | API access for token lifetime
Refresh Token | Up to 90 days| Browser cookie theft, malware | Persistent access, new access tokens
Primary Refresh Token | Session-based| Mimikatz, AADInternals, malware | Full SSO to all M365/Azure apps
Session Cookie | Varies | XSS, browser exploit, AitM proxy | Full session hijacking
Device Code Token | 15 min auth | Phishing (device code flow abuse)| Attacker gets refresh token via social engineering
Common attack techniques:
AitM Phishing (Adversary-in-the-Middle): Attacker proxies the legitimate login page via tools like Evilginx2, capturing session cookies and tokens after the user completes MFA
Device Code Phishing: Attacker generates a device code, sends it to the victim via email/Teams, victim authenticates, attacker receives the token
PRT Extraction: Attacker with local admin on a device extracts the Primary Refresh Token using Mimikatz () or AADInternals
sekurlsa::cloudap
Browser Cookie Theft: Malware or infostealer exfiltrates browser cookies containing session tokens
Step 2: Configure Entra ID Sign-in Risk Detection
Enable Identity Protection to flag anomalous token usage:
Entra Admin Center > Protection > Identity Protection > Risk Detections
Key risk detections for token theft:
- Anomalous Token : Token has unusual characteristics (claim anomalies)
- Token Issuer Anomaly : Token issued by an unusual token issuer
- Unfamiliar Sign-in : Sign-in from a location not seen before for the user
- Impossible Travel : Sign-ins from geographically distant locations in impossible time
- Malicious IP Address : Sign-in from a known malicious IP
- Suspicious Browser : Sign-in from a suspicious or attacker-controlled browser
Configure risk-based conditional access:
Entra Admin Center > Protection > Conditional Access > New Policy
Policy Name: "Block High-Risk Sign-ins - Token Theft Protection"
Assignments:
Users: All users (exclude break-glass accounts)
Cloud Apps: All cloud apps
Conditions:
Sign-in Risk: High
Grant:
Block access
Policy Name: "Require MFA for Medium-Risk Sign-ins"
Assignments:
Users: All users
Cloud Apps: All cloud apps
Conditions:
Sign-in Risk: Medium
Grant:
Require multifactor authentication
Require password change
Step 3: Enable Token Protection (Preview)
Configure Token Protection to bind sign-in session tokens to the device:
Entra Admin Center > Protection > Conditional Access > New Policy
Policy Name: "Enforce Token Protection for Desktop Sessions"
Assignments:
Users: All users (start with a pilot group)
Cloud Apps: Office 365 Exchange Online, Office 365 SharePoint Online
Conditions:
Device Platforms: Windows
Session:
Require token protection for sign-in sessions (Preview): Enabled
Grant:
Require device to be marked as compliant
OR Require Hybrid Azure AD joined device
Token Protection ensures that access tokens are cryptographically bound to the device's Trusted Platform Module (TPM). If an attacker steals a token and replays it from a different device, the token is rejected because the proof-of-possession key does not match.
Step 4: Detect Token Replay in Sign-in Logs
Query Entra sign-in logs for indicators of token theft:
// KQL query for Microsoft Sentinel or Log Analytics
// Detect sign-ins where the token was issued in one location and used in another
SigninLogs
| where TimeGenerated > ago(7d)
| where RiskDetail contains "token" or RiskEventTypes_V2 has "anomalousToken"
| project TimeGenerated, UserPrincipalName, IPAddress, Location,
RiskDetail, RiskLevelDuringSignIn, AppDisplayName,
DeviceDetail, ClientAppUsed, TokenIssuerType
| sort by TimeGenerated desc
// Detect impossible travel with token reuse
SigninLogs
| where TimeGenerated > ago(7d)
| where ResultType == 0 // Successful sign-ins only
| summarize Locations=make_set(Location), IPs=make_set(IPAddress),
Count=count() by UserPrincipalName, bin(TimeGenerated, 1h)
| where array_length(Locations) > 1
| sort by TimeGenerated desc
// Detect device code flow abuse (often used in phishing)
SigninLogs
| where TimeGenerated > ago(7d)
| where AuthenticationProtocol == "deviceCode"
| project TimeGenerated, UserPrincipalName, IPAddress, Location,
AppDisplayName, DeviceDetail, ResultType
| sort by TimeGenerated desc
// Detect token replay: same token used from multiple IPs
AADNonInteractiveUserSignInLogs
| where TimeGenerated > ago(7d)
| where ResultType == 0
| summarize IPs=make_set(IPAddress), IPCount=dcount(IPAddress)
by UserPrincipalName, CorrelationId
| where IPCount > 1
| sort by IPCount desc
Step 5: Investigate and Respond to Token Theft
When a token theft event is detected, follow this response procedure:
Enable CAE to revoke tokens in near-real-time when conditions change:
Entra Admin Center > Protection > Conditional Access > Continuous Access Evaluation
Settings:
Strictly enforce location policies: Enabled
CAE ensures that when you revoke a user's session or change their
risk level, the enforcement happens within minutes rather than waiting
for the access token to naturally expire (60-90 minutes).
Critical events that trigger immediate token revocation with CAE:
- User account disabled or deleted
- Password changed or reset
- MFA enabled for the user
- Admin explicitly revokes refresh tokens
- Azure AD Identity Protection detects elevated user risk
- Network location change violates conditional access policy
Step 7: Configure Defender for Cloud Apps Session Policies
Set up real-time session monitoring to detect and block suspicious token usage:
Microsoft Defender for Cloud Apps > Policies > Session Policies
Policy: "Block download from unmanaged device with stolen token"
Session Control Type: Monitor and block activities
Activity Source: App = Office 365, SharePoint Online
Activity Filter: Device tag does not equal "Compliant"
Activity Type: Download
Action: Block
Policy: "Alert on mass file download (exfiltration via stolen token)"
Session Control Type: Monitor only
Activity Source: App = Office 365
Activity Filter: Repeated activity > 10 downloads in 5 minutes
Action: Alert administrators
Key Concepts
Term
Definition
Primary Refresh Token (PRT)
A long-lived token issued to a registered device that provides SSO to all Azure AD-integrated applications, cryptographically bound to the device's TPM
Token Protection
Entra ID conditional access feature that binds sign-in session tokens to the device, preventing replay from other devices
Continuous Access Evaluation (CAE)
Protocol that enables near-real-time enforcement of security policies by allowing resource providers to subscribe to Entra ID critical events
AitM (Adversary-in-the-Middle)
Phishing technique where an attacker proxies the legitimate authentication flow to capture session cookies after the victim completes MFA
Device Code Flow
OAuth 2.0 authorization grant for input-constrained devices; abused by attackers who send device codes to victims via phishing
Proof of Possession (PoP)
Cryptographic mechanism where a token includes a claim tied to a device key, ensuring the token can only be used by the device that obtained it
Refresh Token
Long-lived OAuth token (up to 90 days) used to obtain new access tokens without re-authentication; primary target for persistent access
Verification
Identity Protection risk detections are enabled and generating alerts for anomalous token activity
Conditional access policies block high-risk sign-ins and require MFA for medium-risk
Token Protection policy is applied to pilot group and confirmed working (test from unregistered device fails)
KQL queries in Sentinel return results when tested against synthetic token anomaly events
Continuous Access Evaluation is enabled and verified (revoke session, confirm access blocked within minutes)
Defender for Cloud Apps session policies are active and monitoring download activity
Device code flow is restricted via conditional access (block or require compliant device)
Incident response runbook includes token revocation, password reset, and OAuth consent review steps
Mail forwarding rules and OAuth app grants are audited for compromised accounts
