diff --git a/docs/configuration.md b/docs/configuration.md
index e04d491..75f6a84 100644
--- a/docs/configuration.md
+++ b/docs/configuration.md
@@ -8,10 +8,10 @@ This guide covers all configuration options available in Readur through environm
 
 - [Environment Variables](#environment-variables)
   - [Core Configuration](#core-configuration)
-  - [File Storage & Upload](#file-storage--upload)
+  - [File Storage & Upload](#file-storage-upload)
   - [Watch Folder Configuration](#watch-folder-configuration)
-  - [OCR & Processing Settings](#ocr--processing-settings)
-  - [Search & Performance](#search--performance)
+  - [OCR & Processing Settings](#ocr-processing-settings)
+  - [Search & Performance](#search-performance)
   - [Data Management](#data-management)
 - [Port Configuration](#port-configuration)
 - [Example Configurations](#example-configurations)
diff --git a/docs/deployment.md b/docs/deployment.md
index dc742f6..7c382b2 100644
--- a/docs/deployment.md
+++ b/docs/deployment.md
@@ -427,7 +427,7 @@ docker run --read-only --tmpfs /tmp ...
 
 ## Next Steps
 
-- Configure [monitoring and alerting](monitoring-usage)
-- Review [security best practices](security)
+- Configure [monitoring and alerting](health-monitoring-guide.md)
+- Review [security best practices](security-guide.md)
 - Set up [automated backups](#backup-strategy)
 - Explore [database guardrails](dev/DATABASE_GUARDRAILS.md)
\ No newline at end of file
diff --git a/docs/guide/overview.md b/docs/guide/overview.md
index 28b0bd1..bff9641 100644
--- a/docs/guide/overview.md
+++ b/docs/guide/overview.md
@@ -90,7 +90,7 @@ Start here if you need to:
 1. [Set up sources](../sources-guide.md)
 2. [Configure watch folders](../WATCH_FOLDER.md)
 3. [Use the API](../api-reference.md)
-4. [Automate workflows](../api-reference.md#automation-examples)
+4. [Automate workflows](../api-reference.md#examples)
 
 ## Feature Highlights
 
diff --git a/docs/quickstart/docker.md b/docs/quickstart/docker.md
index c64cd40..cd580f0 100644
--- a/docs/quickstart/docker.md
+++ b/docs/quickstart/docker.md
@@ -259,7 +259,7 @@ docker system prune -a
 For production use:
 1. [Configure HTTPS](../self-hosting/reverse-proxy.md)
 2. [Set up backups](../self-hosting/backup.md)
-3. [Enable monitoring](../administration/monitoring.md)
+3. [Enable monitoring](../health-monitoring-guide.md)
 4. [Configure authentication](../self-hosting/authentication.md)
 
 ### Scaling
@@ -272,6 +272,6 @@ Handle more documents:
 ## Related Documentation
 
 - [Self-Hosting Guide](../self-hosting/index.md) - Complete deployment guide
-- [Docker Compose Reference](../reference/docker-compose.md) - All configuration options
+- [Configuration Reference](../configuration-reference.md) - All configuration options
 - [Container Architecture](../architecture.md) - How services interact
 - [Troubleshooting Guide](../troubleshooting.md) - Common issues and solutions
\ No newline at end of file
diff --git a/docs/self-hosting/index.md b/docs/self-hosting/index.md
index c3773d0..710bdb2 100644
--- a/docs/self-hosting/index.md
+++ b/docs/self-hosting/index.md
@@ -24,7 +24,7 @@ Direct installation on Linux servers:
 - **From source**: Build and install manually
 - **SystemD services**: Managed by system init
 
-[Bare Metal Installation →](./bare-metal.md)
+[Bare Metal Installation →](../deployment.md)
 
 ### Cloud Platform Deployment
 
@@ -35,7 +35,7 @@ Deploy on managed cloud services:
 - **Azure**: Virtual Machines, Database, Blob Storage
 - **DigitalOcean**: Droplets, Managed Database, Spaces
 
-[Cloud Deployment Guide →](./cloud-deployment.md)
+[Cloud Deployment Guide →](../deployment.md)
 
 ## System Requirements
 
@@ -92,7 +92,7 @@ docker-compose ps
 curl http://localhost:8000/health
 ```
 
-[Detailed Docker Guide →](./docker-setup.md)
+[Detailed Docker Guide →](../quickstart/docker.md)
 
 ### Method 2: Kubernetes (Container Orchestration)
 
@@ -121,7 +121,7 @@ spec:
         - containerPort: 8000
 ```
 
-[Kubernetes Deployment →](./kubernetes.md)
+[Kubernetes Deployment →](../deployment.md#kubernetes)
 
 ### Method 3: Ansible Automation
 
@@ -139,7 +139,7 @@ Automated deployment across multiple servers:
     postgres_version: "14"
 ```
 
-[Ansible Playbook →](./ansible.md)
+[Ansible Playbook →](../deployment.md)
 
 ## Configuration
 
@@ -163,7 +163,7 @@ S3_ACCESS_KEY_ID=<your-key>
 S3_SECRET_ACCESS_KEY=<your-secret>
 ```
 
-[Complete Configuration Reference →](./configuration.md)
+[Complete Configuration Reference →](../configuration-reference.md)
 
 ### Storage Configuration
 
@@ -306,7 +306,7 @@ docker-compose exec readur psql -U readur -d readur -c "SELECT COUNT(*) FROM doc
 - [ ] Regular security updates
 - [ ] Implement rate limiting
 
-[Security Best Practices →](./security.md)
+[Security Best Practices →](../security-guide.md)
 
 ### SSL/TLS Configuration
 
@@ -378,7 +378,7 @@ docker-compose exec readur alembic upgrade head
 docker-compose down && docker-compose up -d
 ```
 
-[Update Procedures →](./updates.md)
+[Update Procedures →](../migration-guide.md)
 
 ## Troubleshooting
 
@@ -415,7 +415,7 @@ psql $DATABASE_URL -c "SELECT 1"
 telnet postgres_host 5432
 ```
 
-[Complete Troubleshooting Guide →](./troubleshooting.md)
+[Complete Troubleshooting Guide →](../troubleshooting.md)
 
 ## Migration from Other Systems
 
@@ -438,7 +438,7 @@ python migrate_mayan.py \
   --target-db postgresql://readur_db
 ```
 
-[Migration Guide →](./migration.md)
+[Migration Guide →](../migration-guide.md)
 
 ## Support and Resources
 
diff --git a/docs/user-guide.md b/docs/user-guide.md
index b93bf63..7e6ff46 100644
--- a/docs/user-guide.md
+++ b/docs/user-guide.md
@@ -427,7 +427,7 @@ Readur supports both local and OIDC users in the same installation:
 - [🔌 API Reference](api-reference.md)  
   REST API for automation and integration
   
-- [🏗️ Developer Documentation](dev/)  
+- [🏗️ Developer Documentation](dev/README.md)  
   Architecture and development setup
   
 - [🔍 OCR Optimization](dev/OCR_OPTIMIZATION_GUIDE.md)