From cybersecurity-skills
Detects OAuth token theft, replay attacks, PRT abuse, and pass-the-cookie in Microsoft Entra ID (Azure AD) via conditional access, sign-in anomalies, and log analysis.
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- Investigating alerts for impossible travel or anomalous token usage in Microsoft Entra ID
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Do not use for on-premises Kerberos ticket attacks (pass-the-ticket, golden ticket); use Active Directory-specific investigation techniques for those scenarios.
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:
sekurlsa::cloudap) or AADInternalsEnable 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
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.
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
When a token theft event is detected, follow this response procedure:
# Step 5a: Revoke all refresh tokens for the compromised user
# Microsoft Graph PowerShell
Connect-MgGraph -Scopes "User.ReadWrite.All"
Revoke-MgUserSignInSession -UserId "user@contoso.com"
# Step 5b: Force password reset
Update-MgUser -UserId "user@contoso.com" -PasswordProfile @{
ForceChangePasswordNextSignIn = $true
}
# Step 5c: Review and revoke OAuth app consent grants
# Check for malicious app consent (common post-compromise persistence)
Get-MgUserOauth2PermissionGrant -UserId "user@contoso.com" |
Select-Object ClientId, ConsentType, Scope
# Remove suspicious OAuth grants
Remove-MgOauth2PermissionGrant -OAuth2PermissionGrantId "<grant-id>"
# Step 5d: Review enterprise app registrations for rogue apps
Get-MgServicePrincipal -Filter "displayName eq 'Suspicious App'" |
Select-Object AppId, DisplayName, SignInAudience
# Step 5e: Check for mail forwarding rules (common post-compromise action)
Get-MgUserMailFolderRule -UserId "user@contoso.com" -MailFolderId "Inbox" |
Where-Object { $_.Actions.ForwardTo -ne $null -or $_.Actions.RedirectTo -ne $null }
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
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
| 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 |