diff --git a/docs/data-sources/builtin-toolsets/index.md b/docs/data-sources/builtin-toolsets/index.md
index 04cba3a6b..315ef9c5e 100644
--- a/docs/data-sources/builtin-toolsets/index.md
+++ b/docs/data-sources/builtin-toolsets/index.md
@@ -2,44 +2,240 @@
 
 HolmesGPT includes pre-built integrations for popular monitoring and observability tools. Some work automatically with Kubernetes, while others require API keys or configuration.
 
-## Available Toolsets
+## Getting Started
+
+💡 **New to HolmesGPT?** Start with [Kubernetes](kubernetes.md) and [Prometheus](prometheus.md) for basic cluster monitoring.
+
+**Quick Setup Process:**
+
+1. **Choose toolsets** from the categories below that match your infrastructure
+2. **Configure authentication** - some need API keys, others work automatically
+3. **Run a test investigation** to verify data access
+
+---
+
+## Kubernetes & Container Platforms
+
+Core integrations for container orchestration and deployment platforms.
 
 <div class="grid cards" markdown>
 
--   [:material-heart-pulse:{ .lg .middle } **AKS Node Health**](aks-node-health.md)
--   [:simple-argo:{ .lg .middle } **ArgoCD**](argocd.md)
--   [:material-aws:{ .lg .middle } **AWS**](aws.md)
+-   [:simple-kubernetes:{ .lg .middle } **Kubernetes**](kubernetes.md)
+
+    ---
+
+    Essential toolset for pod, service, and cluster troubleshooting
+
 -   [:material-microsoft-azure:{ .lg .middle } **Azure Kubernetes Service**](aks.md)
--   [:material-database:{ .lg .middle } **Azure SQL Database**](azure-sql.md)
--   [:simple-confluence:{ .lg .middle } **Confluence**](confluence.md)
--   [:material-chart-line:{ .lg .middle } **Coralogix logs**](coralogix-logs.md)
--   [:simple-datadog:{ .lg .middle } **Datadog**](datadog.md)
--   [:material-clock:{ .lg .middle } **Datetime**](datetime.md)
+
+    ---
+
+    Azure-specific Kubernetes cluster insights
+
+-   [:simple-argo:{ .lg .middle } **ArgoCD**](argocd.md)
+
+    ---
+
+    GitOps deployment status and application health
+
 -   [:simple-docker:{ .lg .middle } **Docker**](docker.md)
--   [:material-github:{ .lg .middle } **GitHub**](github.md)
+
+    ---
+
+    Container runtime and image troubleshooting
+
 -   [:material-package:{ .lg .middle } **Helm**](helm.md)
--   [:material-web:{ .lg .middle } **Internet**](internet.md)
--   [:simple-apachekafka:{ .lg .middle } **Kafka**](kafka.md)
--   [:simple-kubernetes:{ .lg .middle } **Kubernetes**](kubernetes.md)
--   [:simple-grafana:{ .lg .middle } **Loki**](grafanaloki.md)
--   [:simple-mongodb:{ .lg .middle } **MongoDB Atlas**](mongodb-atlas.md)
--   [:simple-newrelic:{ .lg .middle } **New Relic**](newrelic.md)
--   [:simple-notion:{ .lg .middle } **Notion**](notion.md)
--   [:simple-opensearch:{ .lg .middle } **OpenSearch logs**](opensearch-logs.md)
--   [:simple-opensearch:{ .lg .middle } **OpenSearch status**](opensearch-status.md)
+
+    ---
+
+    Kubernetes package manager troubleshooting
+
+-   [:material-heart-pulse:{ .lg .middle } **AKS Node Health**](aks-node-health.md)
+
+    ---
+
+    Azure Kubernetes node diagnostics
+
+</div>
+
+## Monitoring & Observability
+
+Metrics, alerts, and performance monitoring integrations.
+
+<div class="grid cards" markdown>
+
 -   [:simple-prometheus:{ .lg .middle } **Prometheus**](prometheus.md)
--   [:simple-rabbitmq:{ .lg .middle } **RabbitMQ**](rabbitmq.md)
+
+    ---
+
+    Metrics queries and alerting analysis
+
+-   [:simple-datadog:{ .lg .middle } **DataDog**](datadog.md)
+
+    ---
+
+    Full-stack monitoring and APM insights
+
+-   [:simple-newrelic:{ .lg .middle } **New Relic**](newrelic.md)
+
+    ---
+
+    Application performance and infrastructure monitoring
+
 -   [:material-robot:{ .lg .middle } **Robusta**](robusta.md)
+
+    ---
+
+    Kubernetes monitoring and automation platform
+
+</div>
+
+## Logs & Analytics
+
+Log aggregation, search, and distributed tracing tools.
+
+<div class="grid cards" markdown>
+
+-   [:simple-grafana:{ .lg .middle } **Loki**](grafanaloki.md)
+
+    ---
+
+    Log aggregation and search via Grafana
+
+-   [:simple-grafana:{ .lg .middle } **Tempo**](grafanatempo.md)
+
+    ---
+
+    Distributed tracing analysis
+
+-   [:simple-opensearch:{ .lg .middle } **OpenSearch**](opensearch-logs.md)
+
+    ---
+
+    Enterprise search and analytics platform
+
+-   [:material-chart-line:{ .lg .middle } **Coralogix**](coralogix-logs.md)
+
+    ---
+
+    Cloud-native observability platform
+
+</div>
+
+## Cloud Providers
+
+Cloud-specific services and database integrations.
+
+<div class="grid cards" markdown>
+
+-   [:material-aws:{ .lg .middle } **AWS**](aws.md)
+
+    ---
+
+    Amazon Web Services resources and APIs
+
+-   [:material-database:{ .lg .middle } **Azure SQL Database**](azure-sql.md)
+
+    ---
+
+    Azure database performance and health
+
+-   [:simple-mongodb:{ .lg .middle } **MongoDB Atlas**](mongodb-atlas.md)
+
+    ---
+
+    Cloud database monitoring and diagnostics
+
+</div>
+
+## Collaboration & Documentation
+
+Knowledge bases, issue tracking, and team communication tools.
+
+<div class="grid cards" markdown>
+
+-   [:material-github:{ .lg .middle } **GitHub**](github.md)
+
+    ---
+
+    Repository insights and issue analysis
+
+-   [:simple-confluence:{ .lg .middle } **Confluence**](confluence.md)
+
+    ---
+
+    Team knowledge base and documentation
+
 -   [:material-ticket:{ .lg .middle } **ServiceNow**](servicenow.md)
+
+    ---
+
+    IT service management and incident tracking
+
+-   [:simple-notion:{ .lg .middle } **Notion**](notion.md)
+
+    ---
+
+    Workspace documentation and knowledge sharing
+
 -   [:material-forum:{ .lg .middle } **Slab**](slab.md)
--   [:simple-grafana:{ .lg .middle } **Tempo**](grafanatempo.md)
+
+    ---
+
+    Modern team hub for documentation and knowledge
 
 </div>
 
-## Getting Started
+## Message Queues
 
-1. **Choose toolsets** that match your infrastructure (Prometheus, Grafana, etc.)
-2. **Configure authentication** - some need API keys, others work automatically
-3. **Run a test investigation** to verify data access
+Messaging systems and distributed streaming platforms.
+
+<div class="grid cards" markdown>
+
+-   [:simple-apachekafka:{ .lg .middle } **Kafka**](kafka.md)
+
+    ---
+
+    Distributed streaming platform monitoring
+
+-   [:simple-rabbitmq:{ .lg .middle } **RabbitMQ**](rabbitmq.md)
+
+    ---
+
+    Message broker performance and queue analysis
+
+</div>
+
+## Utilities
+
+General-purpose utility toolsets for specialized functions.
+
+<div class="grid cards" markdown>
+
+-   [:material-bash:{ .lg .middle } **Bash**](bash.md)
+
+    ---
+
+    Secure command-line tool execution and system analysis
+
+-   [:material-clock:{ .lg .middle } **Datetime**](datetime.md)
+
+    ---
+
+    Time-based utilities for investigations
+
+-   [:material-web:{ .lg .middle } **Internet**](internet.md)
+
+    ---
+
+    External connectivity and web resource checks
+
+</div>
+
+---
+
+## Additional Resources
 
-💡 **Tip**: Start with [Kubernetes](kubernetes.md) and [Prometheus](prometheus.md) for basic cluster monitoring.
+- **[Custom Toolsets](../custom-toolsets.md)** - Create your own integrations
+- **[Remote MCP Servers](../remote-mcp-servers.md)** - Connect external MCP servers
+- **[Adding Permissions](../permissions.md)** - Configure RBAC for additional resources
diff --git a/mkdocs.yml b/mkdocs.yml
index a9c90c155..55260f266 100644
--- a/mkdocs.yml
+++ b/mkdocs.yml
@@ -167,33 +167,41 @@ nav:
       - data-sources/index.md
       - Built-in Toolsets:
           - data-sources/builtin-toolsets/index.md
-          - AKS Node Health: data-sources/builtin-toolsets/aks-node-health.md
-          - ArgoCD: data-sources/builtin-toolsets/argocd.md
-          - AWS: data-sources/builtin-toolsets/aws.md
-          - Azure Kubernetes Service: data-sources/builtin-toolsets/aks.md
-          - Azure SQL Database: data-sources/builtin-toolsets/azure-sql.md
-          - Confluence: data-sources/builtin-toolsets/confluence.md
-          - Coralogix logs: data-sources/builtin-toolsets/coralogix-logs.md
-          - DataDog: data-sources/builtin-toolsets/datadog.md
-          - Datetime: data-sources/builtin-toolsets/datetime.md
-          - Docker: data-sources/builtin-toolsets/docker.md
-          - GitHub: data-sources/builtin-toolsets/github.md
-          - Loki: data-sources/builtin-toolsets/grafanaloki.md
-          - Tempo: data-sources/builtin-toolsets/grafanatempo.md
-          - Helm: data-sources/builtin-toolsets/helm.md
-          - Internet: data-sources/builtin-toolsets/internet.md
-          - Kafka: data-sources/builtin-toolsets/kafka.md
-          - Kubernetes: data-sources/builtin-toolsets/kubernetes.md
-          - MongoDB Atlas: data-sources/builtin-toolsets/mongodb-atlas.md
-          - New Relic: data-sources/builtin-toolsets/newrelic.md
-          - Notion: data-sources/builtin-toolsets/notion.md
-          - OpenSearch logs: data-sources/builtin-toolsets/opensearch-logs.md
-          - OpenSearch status: data-sources/builtin-toolsets/opensearch-status.md
-          - Prometheus: data-sources/builtin-toolsets/prometheus.md
-          - RabbitMQ: data-sources/builtin-toolsets/rabbitmq.md
-          - Robusta: data-sources/builtin-toolsets/robusta.md
-          - ServiceNow: data-sources/builtin-toolsets/servicenow.md
-          - Slab: data-sources/builtin-toolsets/slab.md
+          - Kubernetes & Containers:
+              - Kubernetes: data-sources/builtin-toolsets/kubernetes.md
+              - Azure Kubernetes Service: data-sources/builtin-toolsets/aks.md
+              - AKS Node Health: data-sources/builtin-toolsets/aks-node-health.md
+              - ArgoCD: data-sources/builtin-toolsets/argocd.md
+              - Docker: data-sources/builtin-toolsets/docker.md
+              - Helm: data-sources/builtin-toolsets/helm.md
+          - Monitoring & Observability:
+              - Prometheus: data-sources/builtin-toolsets/prometheus.md
+              - DataDog: data-sources/builtin-toolsets/datadog.md
+              - New Relic: data-sources/builtin-toolsets/newrelic.md
+              - Robusta: data-sources/builtin-toolsets/robusta.md
+          - Logs & Analytics:
+              - Loki: data-sources/builtin-toolsets/grafanaloki.md
+              - Tempo: data-sources/builtin-toolsets/grafanatempo.md
+              - Coralogix logs: data-sources/builtin-toolsets/coralogix-logs.md
+              - OpenSearch logs: data-sources/builtin-toolsets/opensearch-logs.md
+              - OpenSearch status: data-sources/builtin-toolsets/opensearch-status.md
+          - Cloud Providers:
+              - AWS: data-sources/builtin-toolsets/aws.md
+              - Azure SQL Database: data-sources/builtin-toolsets/azure-sql.md
+              - MongoDB Atlas: data-sources/builtin-toolsets/mongodb-atlas.md
+          - Collaboration & Documentation:
+              - Confluence: data-sources/builtin-toolsets/confluence.md
+              - GitHub: data-sources/builtin-toolsets/github.md
+              - Notion: data-sources/builtin-toolsets/notion.md
+              - ServiceNow: data-sources/builtin-toolsets/servicenow.md
+              - Slab: data-sources/builtin-toolsets/slab.md
+          - Message Queues:
+              - Kafka: data-sources/builtin-toolsets/kafka.md
+              - RabbitMQ: data-sources/builtin-toolsets/rabbitmq.md
+          - Utilities:
+              - Bash: data-sources/builtin-toolsets/bash.md
+              - Datetime: data-sources/builtin-toolsets/datetime.md
+              - Internet: data-sources/builtin-toolsets/internet.md
 
       - Custom Toolsets: data-sources/custom-toolsets.md
       - Remote MCP Servers: data-sources/remote-mcp-servers.md