Troubleshooting: Common Microsoft Entra SDK for AgentID Issues

Solutions for common SDK deployment and operational issues.

Quick Diagnostics

Check SDK Health

# Check if SDK is running
kubectl get pods -l app=myapp

# Check SDK logs
kubectl logs <pod-name> -c sidecar

# Test health endpoint
kubectl exec <pod-name> -c sidecar -- curl http://localhost:5000/health

Check Configuration

# View SDK environment variables
kubectl exec <pod-name> -c sidecar -- env | grep AzureAd

# Check ConfigMap
kubectl get configmap sidecar-config -o yaml

# Check Secrets
kubectl get secret sidecar-secrets -o yaml

Common Issues

Container Won't Start

Symptom

Pod shows CrashLoopBackOff or Error status.

Possible Causes

Missing Required Configuration

# Check logs for configuration errors
kubectl logs <pod-name> -c sidecar

# Look for messages like:
# "AzureAd:TenantId is required"
# "AzureAd:ClientId is required"

Solution:

# Ensure all required configuration is set
env:
- name: AzureAd__TenantId
  value: "<your-tenant-id>"
- name: AzureAd__ClientId
  value: "<your-client-id>"

Invalid Credential Configuration

# Check for credential errors in logs
kubectl logs <pod-name> -c sidecar | grep -i "credential"

Solution: Verify credential configuration and access to Key Vault or secrets.

Port Conflict

# Check if port 5000 is already in use
kubectl exec <pod-name> -c sidecar -- netstat -tuln | grep 5000

Solution: Change SDK port if needed:

env:
- name: ASPNETCORE_URLS
  value: "http://+:5001"

401 Unauthorized Errors

Symptom

Requests to SDK return 401 Unauthorized.

Possible Causes

Missing Authorization Header

# Test with curl
curl -v http://localhost:5000/AuthorizationHeader/Graph
# Should show 401 because no Authorization header

Solution: Include Authorization header:

curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/AuthorizationHeader/Graph

Invalid or Expired Token

# Check token claims
kubectl exec <pod-name> -c sidecar -- curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/Validate

Solution: Obtain a new token from Microsoft Entra ID.

Audience Mismatch

# Check logs for audience validation errors
kubectl logs <pod-name> -c sidecar | grep -i "audience"

Solution: Verify audience configuration matches token:

env:
- name: AzureAd__Audience
  value: "api://<your-api-id>"

Scope Validation Failure

# Check logs for scope errors
kubectl logs <pod-name> -c sidecar | grep -i "scope"

Solution: Ensure token contains required scopes:

env:
- name: AzureAd__Scopes
  value: "access_as_user"  # Or remove to disable scope validation

To understand the detailed errors, you might need to increase the log level:

Logging__LogLevel__Default=Debug 
Logging__LogLevel__Microsoft.Identity.Web=Debug 
Logging__LogLevel__Microsoft.AspNetCore=Debug 

400 Bad Request - Agent Identity Validation

Symptom

Requests with agent identity parameters return 400 Bad Request.

Error: AgentUsername Without AgentIdentity

Request:

curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentUsername=user@contoso.com"

Error Response:

{
  "status": 400,
  "detail": "AgentUsername requires AgentIdentity to be specified"
}

Solution: Include AgentIdentity parameter:

curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentIdentity=<client-id>&AgentUsername=user@contoso.com"

Error: AgentUsername and AgentUserId Both Specified

Request:

curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentIdentity=<id>&AgentUsername=user@contoso.com&AgentUserId=<oid>"

Error Response:

{
  "status": 400,
  "detail": "AgentUsername and AgentUserId are mutually exclusive"
}

Solution: Use only one:

# Use AgentUsername
curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentIdentity=<id>&AgentUsername=user@contoso.com"

# OR use AgentUserId
curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentIdentity=<id>&AgentUserId=<oid>"

Error: Invalid AgentUserId Format

Request:

curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentIdentity=<id>&AgentUserId=invalid-guid"

Error Response:

{
  "status": 400,
  "detail": "AgentUserId must be a valid GUID"
}

Solution: Provide a valid GUID:

curl -H "Authorization: Bearer <token>" \
  "http://localhost:5000/AuthorizationHeader/Graph?AgentIdentity=<id>&AgentUserId=12345678-1234-1234-1234-123456789012"

404 Not Found - Service Not Configured

Symptom

{
  "status": 404,
  "detail": "Downstream API 'UnknownService' not configured"
}

Possible Causes

Service Name Typo

# Wrong service name in URL
curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/AuthorizationHeader/Grafh
# Should be "Graph"

Solution: Use correct service name from configuration.

Missing DownstreamApis Configuration

Solution: Add service configuration:

env:
- name: DownstreamApis__Graph__BaseUrl
  value: "https://graph.microsoft.com/v1.0"
- name: DownstreamApis__Graph__Scopes
  value: "User.Read"

Token Acquisition Failures

Symptom

500 Internal Server Error when acquiring tokens.

AADSTS Error Codes

AADSTS50076: Multi-Factor Authentication Required

AADSTS50076: Due to a configuration change made by your administrator, 
or because you moved to a new location, you must use multi-factor authentication.

Solution: User must complete MFA. This is expected behavior for conditional access policies.

AADSTS65001: User Consent Required

AADSTS65001: The user or administrator has not consented to use the application.

Solution:

1. Request admin consent for the application
2. Ensure delegated permissions are properly configured

AADSTS700016: Application Not Found

AADSTS700016: Application with identifier '<client-id>' was not found.

Solution: Verify ClientId is correct and application exists in tenant.

AADSTS7000215: Invalid Client Secret

AADSTS7000215: Invalid client secret is provided.

Solution:

1. Verify client secret is correct
2. Check if secret has expired
3. Generate new secret and update configuration

AADSTS700027: Certificate or Private Key Not Configured

AADSTS700027: The certificate with identifier '<thumbprint>' was not found.

Solution:

1. Verify certificate is registered in app registration
2. Check certificate configuration in the SDK
3. Ensure certificate is accessible from container

Token Cache Issues

Solution: Clear token cache and restart:

kubectl rollout restart deployment <deployment-name>

For distributed cache (Redis):

# Clear Redis cache
redis-cli FLUSHDB

Network Connectivity Issues

Cannot Reach Microsoft Entra ID

Symptom: Timeout errors when acquiring tokens.

Diagnostics:

# Test connectivity from SDK container
kubectl exec <pod-name> -c sidecar -- curl -v https://login.microsoftonline.com

# Check DNS resolution
kubectl exec <pod-name> -c sidecar -- nslookup login.microsoftonline.com

Solution:

• Check network policies
• Verify firewall rules allow HTTPS to login.microsoftonline.com
• Ensure DNS is working correctly

Cannot Reach Downstream APIs

Diagnostics:

# Test connectivity to downstream API
kubectl exec <pod-name> -c sidecar -- curl -v https://graph.microsoft.com

# Check configuration
kubectl exec <pod-name> -c sidecar -- env | grep DownstreamApis__Graph__BaseUrl

Solution:

• Verify downstream API URL is correct
• Check network egress rules
• Ensure API is accessible from cluster

Application cannot reach the SDK

Symptom

Application shows connection errors when calling the SDK.

Diagnostics:

# Test from application container
kubectl exec <pod-name> -c app -- curl -v http://localhost:5000/health

# Check if sidecar is listening
kubectl exec <pod-name> -c sidecar -- netstat -tuln | grep 5000

Solution:

• Verify SIDECAR_URL environment variable
• Check the SDK is running: kubectl get pods
• Ensure port 5000 is not blocked

Performance Issues

Slow Token Acquisition

Diagnostics:

# Enable detailed logging
# Add to SDK configuration:
# - name: Logging__LogLevel__Microsoft.Identity.Web
#   value: "Debug"

# Check logs for timing information
kubectl logs <pod-name> -c sidecar | grep "Token acquisition"

Solutions:

1. Check Token Cache: Ensure caching is enabled and working
2. Increase Resources: Allocate more CPU/memory to the SDK
3. Network Latency: Check latency to Microsoft Entra ID
4. Connection Pooling: Verify HTTP connection reuse

High Memory Usage

Diagnostics:

# Check resource usage
kubectl top pod <pod-name> --containers

# Check for memory leaks in logs
kubectl logs <pod-name> -c sidecar | grep -i "memory"

Solutions:

1. Increase memory limits
2. Check for token cache size issues
3. Review application usage patterns
4. Consider distributed cache for multiple replicas

Certificate Issues

Certificate Not Found

Symptom:

Certificate with thumbprint '<thumbprint>' not found in certificate store.

Solution:

• Verify certificate is mounted correctly
• Check certificate store path
• Ensure certificate permissions are correct

Certificate Expired

Symptom:

The certificate has expired.

Solution:

1. Generate new certificate
2. Register in Microsoft Entra ID
3. Update SDK configuration
4. Redeploy containers

Key Vault Access Denied

Symptom:

Access denied to Key Vault '<vault-name>'.

Solution:

• Verify managed identity has access policy to Key Vault
• Check Key Vault firewall rules
• Ensure certificate exists in Key Vault

Signed HTTP Request (SHR) Issues

Invalid PoP Token

Symptom: Downstream API rejects PoP token.

Diagnostics:

# Check if PoP token is being requested
kubectl logs <pod-name> -c sidecar | grep -i "pop"

# Verify PopPublicKey is configured correctly
kubectl exec <pod-name> -c sidecar -- env | grep PopPublicKey

Solution:

• Verify public key is correctly base64 encoded
• Ensure downstream API supports PoP tokens
• Check PoP token format

Missing Private Key

Symptom: Cannot sign HTTP request.

Solution: Ensure private key is available to application for signing requests.

Error Reference Table

Debugging Tools

Enable Detailed Logging

env:
- name: Logging__LogLevel__Default
  value: "Debug"
- name: Logging__LogLevel__Microsoft.Identity.Web
  value: "Trace"
- name: Logging__LogLevel__Microsoft.AspNetCore
  value: "Debug"

Warning: Debug/Trace logging may log sensitive information. Use only in development or temporarily in production.

Test Token Validation

# Validate token
curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/Validate | jq .

# Check claims
curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/Validate | jq '.claims'

Test Token Acquisition

# Get authorization header
curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/AuthorizationHeader/Graph | jq .

# Extract and decode token
curl -H "Authorization: Bearer <token>" \
  http://localhost:5000/AuthorizationHeader/Graph | \
  jq -r '.authorizationHeader' | \
  cut -d' ' -f2 | \
  jwt decode -

Monitor with Application Insights

If configured:

# Query Application Insights
az monitor app-insights query \
  --app <app-insights-name> \
  --analytics-query "traces | where message contains 'token acquisition' | take 100"

Getting Help

Collect Diagnostic Information

When opening an issue, include:

1. SDK Version:

   kubectl describe pod <pod-name> | grep -A 5 "sidecar:"
   

2. Configuration (redact sensitive data):

   kubectl get configmap sidecar-config -o yaml
   

3. Logs (last 100 lines):

   kubectl logs <pod-name> -c sidecar --tail=100
   

4. Error Messages: Full error response from the SDK

5. Request Details: HTTP method, endpoint, parameters used

Support Resources

• GitHub Issues: microsoft-identity-web/issues
• Microsoft Q&A: Microsoft Identity Platform
• Stack Overflow: Tag [microsoft-identity-web]

Best Practices for Troubleshooting

1. Start with Health Check: Always verify the SDK is healthy first
2. Check Logs: SDK logs contain valuable diagnostic information
3. Verify Configuration: Ensure all required settings are present and correct
4. Test Incrementally: Start with simple requests, add complexity gradually
5. Use Correlation IDs: Include correlation IDs for tracing across services
6. Monitor Continuously: Set up alerts for authentication failures
7. Document Issues: Keep notes on issues and resolutions for future reference

Related Resources

• Installation Guide
• Configuration Reference
• Security Best Practices
• FAQ