diff --git a/.github/workflows/deploy.yaml b/.github/workflows/deploy.yaml
index 1752765e..d3a42a2e 100644
--- a/.github/workflows/deploy.yaml
+++ b/.github/workflows/deploy.yaml
@@ -65,6 +65,110 @@ jobs:
           uv run npx cdk deploy --ci --all --require-approval never
           cd -
 
+      - name: Get stack outputs and run operational checks
+        id: operational_checks
+        env:
+          PROJECT_ID: ${{ steps.short-sha.outputs.sha }}
+        run: |
+          cd integration_tests/cdk
+
+          echo "=== Retrieving Stack Outputs ==="
+
+          # Get list of deployed stacks
+          DEPLOYED_STACKS=$(uv run npx cdk list)
+          echo "Deployed stacks: $DEPLOYED_STACKS"
+
+          # Create outputs file
+          echo "{}" > stack_outputs.json
+
+          # Get outputs from each stack
+          for STACK_NAME in $DEPLOYED_STACKS; do
+            echo "Processing stack: $STACK_NAME"
+
+            # Try to get outputs using AWS CLI
+            STACK_OUTPUTS=$(aws cloudformation describe-stacks \
+              --stack-name "$STACK_NAME" \
+              --query 'Stacks[0].Outputs' \
+              --output json 2>/dev/null || echo "[]")
+
+            if [ "$STACK_OUTPUTS" != "[]" ] && [ "$STACK_OUTPUTS" != "null" ]; then
+              echo "Found outputs for $STACK_NAME:"
+              echo "$STACK_OUTPUTS" | jq .
+
+              # Convert to key-value format and merge with existing outputs
+              TEMP_OUTPUTS=$(echo "$STACK_OUTPUTS" | jq -r 'if . then [.[] | select(.OutputKey and .OutputValue) | {(.OutputKey): .OutputValue}] | add // {} else {} end')
+              echo "$TEMP_OUTPUTS" > temp_stack_outputs.json
+
+              # Merge with existing outputs
+              jq -s '.[0] * .[1]' stack_outputs.json temp_stack_outputs.json > merged.json
+              mv merged.json stack_outputs.json
+            else
+              echo "No outputs found for $STACK_NAME"
+            fi
+          done
+
+          echo "=== Final Combined Outputs ==="
+          cat stack_outputs.json | jq .
+
+          echo "=== Running Operational Checks ==="
+
+          echo "Available CloudFormation output keys:"
+          cat stack_outputs.json | jq -r 'keys[]'
+
+          STAC_API_URL=$(cat stack_outputs.json | jq -r '
+            to_entries[] |
+            select(.key | test("pgstacapistacapioutput"; "i")) |
+            .value' | head -1)
+
+          TITILER_PGSTAC_API_URL=$(cat stack_outputs.json | jq -r '
+            to_entries[] |
+            select(.key | test("titilerpgstacapioutput"; "i")) |
+            .value' | head -1)
+
+          TIPG_API_URL=$(cat stack_outputs.json | jq -r '
+            to_entries[] |
+            select(.key | test("tipgapioutput"; "i")) |
+            .value' | head -1)
+
+          echo "Extracted URLs:"
+          echo "STAC_API_URL: $STAC_API_URL"
+          echo "TITILER_PGSTAC_API_URL: $TITILER_PGSTAC_API_URL"
+          echo "TIPG_API_URL: $TIPG_API_URL"
+
+          # Array of API URLs to check
+          declare -a API_HEALTH_ENDPOINTS=(
+            "STAC_API_URL:${STAC_API_URL}_mgmt/health"
+            "TITILER_PGSTAC_API_URL:${TITILER_PGSTAC_API_URL}healthz"
+            "TIPG_API_URL:${TIPG_API_URL}healthz"
+          )
+
+          # Check each API
+          echo "=== Sleeping for 5 minutes to ensure everything is running ==="
+          sleep 300
+
+          for API_INFO in "${API_HEALTH_ENDPOINTS[@]}"; do
+            API_NAME=$(echo "$API_INFO" | cut -d: -f1)
+            API_URL=$(echo "$API_INFO" | cut -d: -f2-)
+
+            if [ -n "$API_URL" ] && [ "$API_URL" != "null" ]; then
+              echo "Checking $API_NAME at: $API_URL"
+
+              HTTP_STATUS=$(curl -s -o /dev/null -w "%{http_code}" --max-time 30 "$API_URL" || echo "000")
+
+              if [ "$HTTP_STATUS" = "200" ]; then
+                echo "✅ $API_NAME returned 200"
+              else
+                echo "❌ $API_NAME returned $HTTP_STATUS"
+                exit 1
+              fi
+            else
+              echo "⚠️ $API_NAME URL not found in stack outputs"
+            fi
+          done
+
+          echo "=== Operational Checks Complete ==="
+          cd -
+
       - name: Tear down any infrastructure
         if: always()
         env:
diff --git a/.gitignore b/.gitignore
index c3f3211c..f6a1fdb6 100644
--- a/.gitignore
+++ b/.gitignore
@@ -12,3 +12,5 @@ tests/*.egg*
 tests/*venv*
 tests/__pycache__
 integration_tests/cdk/cdk.out
+integration_tests/cdk/stack_outputs.json
+integration_tests/cdk/temp_stack_outputs.json
diff --git a/lib/database/PgBouncer.ts b/lib/database/PgBouncer.ts
index a41aaa65..90067cb8 100644
--- a/lib/database/PgBouncer.ts
+++ b/lib/database/PgBouncer.ts
@@ -4,6 +4,7 @@ import {
   aws_lambda as lambda,
   aws_secretsmanager as secretsmanager,
   CustomResource,
+  Duration,
   Stack,
 } from "aws-cdk-lib";
 import { Construct } from "constructs";
@@ -66,6 +67,7 @@ export class PgBouncer extends Construct {
   public readonly pgbouncerSecret: secretsmanager.Secret;
   public readonly securityGroup: ec2.SecurityGroup;
   public readonly secretUpdateComplete: CustomResource;
+  public readonly healthCheck: CustomResource;
 
   // The max_connections parameter in PgBouncer determines the maximum number of
   // connections to open on the actual database instance. We want that number to
@@ -220,6 +222,47 @@ export class PgBouncer extends Construct {
         },
       }
     );
+
+    // Add health check custom resource
+    const healthCheckFunction = new lambda.Function(
+      this,
+      "HealthCheckFunction",
+      {
+        runtime: lambda.Runtime.NODEJS_20_X,
+        handler: "index.handler",
+        timeout: Duration.minutes(10),
+        code: lambda.Code.fromAsset(
+          path.join(__dirname, "lambda/pgbouncer-health-check")
+        ),
+        description: "PgBouncer health check function",
+      }
+    );
+
+    // Grant SSM permissions for health check
+    healthCheckFunction.addToRolePolicy(
+      new iam.PolicyStatement({
+        actions: [
+          "ssm:SendCommand",
+          "ssm:GetCommandInvocation",
+          "ssm:DescribeInstanceInformation",
+          "ssm:ListCommandInvocations",
+        ],
+        resources: ["*"],
+      })
+    );
+
+    this.healthCheck = new CustomResource(this, "PgBouncerHealthCheck", {
+      serviceToken: healthCheckFunction.functionArn,
+      properties: {
+        InstanceId: this.instance.instanceId,
+        // Add timestamp to force re-execution on stack updates
+        Timestamp: new Date().toISOString(),
+      },
+    });
+
+    // Ensure health check runs after instance is created but before secret update
+    this.healthCheck.node.addDependency(this.instance);
+    this.secretUpdateComplete.node.addDependency(this.healthCheck);
   }
 
   private loadUserDataScript(
diff --git a/lib/database/index.ts b/lib/database/index.ts
index 4b32a346..285a56bd 100644
--- a/lib/database/index.ts
+++ b/lib/database/index.ts
@@ -27,9 +27,47 @@ function hasVpc(
 }
 
 /**
- * An RDS instance with pgSTAC installed. This is a wrapper around the
- * `rds.DatabaseInstance` higher-level construct making use
- * of the BootstrapPgStac construct.
+ * An RDS instance with pgSTAC installed and PgBouncer connection pooling.
+ *
+ * This construct creates an optimized pgSTAC database setup that includes:
+ * - RDS PostgreSQL instance with pgSTAC extension
+ * - PgBouncer connection pooler (enabled by default)
+ * - Automated health monitoring system
+ * - Optimized database parameters for the selected instance type
+ *
+ * ## Connection Pooling with PgBouncer
+ *
+ * By default, this construct deploys PgBouncer as a connection pooler running on
+ * a dedicated EC2 instance. PgBouncer provides several benefits:
+ *
+ * - **Connection Management**: Pools and reuses database connections to reduce overhead
+ * - **Performance**: Optimizes connection handling for high-traffic applications
+ * - **Scalability**: Allows more concurrent connections than the RDS instance alone
+ * - **Health Monitoring**: Includes comprehensive health checks to ensure availability
+ *
+ * ### PgBouncer Configuration
+ * - Pool mode: Transaction-level pooling (default)
+ * - Maximum client connections: 1000
+ * - Default pool size: 20 connections per database/user combination
+ * - Instance type: t3.micro EC2 instance
+ *
+ * ### Health Check System
+ * The construct includes an automated health check system that validates:
+ * - PgBouncer service is running and listening on port 5432
+ * - Connection tests to ensure accessibility
+ * - Cloud-init setup completion before validation
+ * - Detailed diagnostics for troubleshooting
+ *
+ * ### Connection Details
+ * When PgBouncer is enabled, applications connect through the PgBouncer instance
+ * rather than directly to RDS. The `pgstacSecret` contains connection information
+ * pointing to PgBouncer, and the `connectionTarget` property refers to the
+ * PgBouncer EC2 instance.
+ *
+ * To disable PgBouncer and connect directly to RDS, set `addPgbouncer: false`.
+ *
+ * This is a wrapper around the `rds.DatabaseInstance` higher-level construct
+ * making use of the BootstrapPgStac construct.
  */
 export class PgStacDatabase extends Construct {
   db: rds.DatabaseInstance;
@@ -40,6 +78,7 @@ export class PgStacDatabase extends Construct {
   public readonly connectionTarget: rds.IDatabaseInstance | ec2.Instance;
   public readonly securityGroup?: ec2.SecurityGroup;
   public readonly secretBootstrapper?: CustomResource;
+  public readonly pgbouncerHealthCheck?: CustomResource;
 
   constructor(scope: Construct, id: string, props: PgStacDatabaseProps) {
     super(scope, id);
@@ -186,6 +225,7 @@ export class PgStacDatabase extends Construct {
       this.connectionTarget = this._pgBouncerServer.instance;
       this.securityGroup = this._pgBouncerServer.securityGroup;
       this.secretBootstrapper = this._pgBouncerServer.secretUpdateComplete;
+      this.pgbouncerHealthCheck = this._pgBouncerServer.healthCheck;
     } else {
       this.connectionTarget = this.db;
     }
diff --git a/lib/database/lambda/package-lock.json b/lib/database/lambda/package-lock.json
index 8ad6a3cb..40854983 100644
--- a/lib/database/lambda/package-lock.json
+++ b/lib/database/lambda/package-lock.json
@@ -8,7 +8,8 @@
       "name": "pgbouncer-secret-updater",
       "version": "1.0.0",
       "dependencies": {
-        "@aws-sdk/client-secrets-manager": "^3.0.0"
+        "@aws-sdk/client-secrets-manager": "^3.0.0",
+        "@aws-sdk/client-ssm": "^3.0.0"
       },
       "devDependencies": {
         "@types/aws-lambda": "^8.10.0",
@@ -194,384 +195,2232 @@
         "node": ">=16.0.0"
       }
     },
-    "node_modules/@aws-sdk/client-sso": {
-      "version": "3.721.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/client-sso/-/client-sso-3.721.0.tgz",
-      "integrity": "sha512-UrYAF4ilpO2cZBFddQmbETfo0xKP3CEcantcMQTc0xPY3quHLZhYuBiRae+McWi6yZpH4ErnFZIWeKSJ2OQgqQ==",
+    "node_modules/@aws-sdk/client-ssm": {
+      "version": "3.886.0",
+      "resolved": "https://registry.npmjs.org/@aws-sdk/client-ssm/-/client-ssm-3.886.0.tgz",
+      "integrity": "sha512-yjc10bl01IXcTGyYkn5CKHQRs44nZaYW/pwvvdwiwRnRqhlq1m8xUJhXuz+MOGKKu0lyehDdJ8sN7NcT2lvi0w==",
       "license": "Apache-2.0",
       "dependencies": {
         "@aws-crypto/sha256-browser": "5.2.0",
         "@aws-crypto/sha256-js": "5.2.0",
-        "@aws-sdk/core": "3.716.0",
-        "@aws-sdk/middleware-host-header": "3.714.0",
-        "@aws-sdk/middleware-logger": "3.714.0",
-        "@aws-sdk/middleware-recursion-detection": "3.714.0",
-        "@aws-sdk/middleware-user-agent": "3.721.0",
-        "@aws-sdk/region-config-resolver": "3.714.0",
-        "@aws-sdk/types": "3.714.0",
-        "@aws-sdk/util-endpoints": "3.714.0",
-        "@aws-sdk/util-user-agent-browser": "3.714.0",
-        "@aws-sdk/util-user-agent-node": "3.721.0",
-        "@smithy/config-resolver": "^3.0.13",
-        "@smithy/core": "^2.5.5",
-        "@smithy/fetch-http-handler": "^4.1.2",
-        "@smithy/hash-node": "^3.0.11",
-        "@smithy/invalid-dependency": "^3.0.11",
-        "@smithy/middleware-content-length": "^3.0.13",
-        "@smithy/middleware-endpoint": "^3.2.6",
-        "@smithy/middleware-retry": "^3.0.31",
-        "@smithy/middleware-serde": "^3.0.11",
-        "@smithy/middleware-stack": "^3.0.11",
-        "@smithy/node-config-provider": "^3.1.12",
-        "@smithy/node-http-handler": "^3.3.2",
-        "@smithy/protocol-http": "^4.1.8",
-        "@smithy/smithy-client": "^3.5.1",
-        "@smithy/types": "^3.7.2",
-        "@smithy/url-parser": "^3.0.11",
-        "@smithy/util-base64": "^3.0.0",
-        "@smithy/util-body-length-browser": "^3.0.0",
-        "@smithy/util-body-length-node": "^3.0.0",
-        "@smithy/util-defaults-mode-browser": "^3.0.31",
-        "@smithy/util-defaults-mode-node": "^3.0.31",
-        "@smithy/util-endpoints": "^2.1.7",
-        "@smithy/util-middleware": "^3.0.11",
-        "@smithy/util-retry": "^3.0.11",
-        "@smithy/util-utf8": "^3.0.0",
-        "tslib": "^2.6.2"
+        "@aws-sdk/core": "3.883.0",
+        "@aws-sdk/credential-provider-node": "3.886.0",
+        "@aws-sdk/middleware-host-header": "3.873.0",
+        "@aws-sdk/middleware-logger": "3.876.0",
+        "@aws-sdk/middleware-recursion-detection": "3.886.0",
+        "@aws-sdk/middleware-user-agent": "3.883.0",
+        "@aws-sdk/region-config-resolver": "3.873.0",
+        "@aws-sdk/types": "3.862.0",
+        "@aws-sdk/util-endpoints": "3.879.0",
+        "@aws-sdk/util-user-agent-browser": "3.873.0",
+        "@aws-sdk/util-user-agent-node": "3.883.0",
+        "@smithy/config-resolver": "^4.1.5",
+        "@smithy/core": "^3.9.2",
+        "@smithy/fetch-http-handler": "^5.1.1",
+        "@smithy/hash-node": "^4.0.5",
+        "@smithy/invalid-dependency": "^4.0.5",
+        "@smithy/middleware-content-length": "^4.0.5",
+        "@smithy/middleware-endpoint": "^4.1.21",
+        "@smithy/middleware-retry": "^4.1.22",
+        "@smithy/middleware-serde": "^4.0.9",
+        "@smithy/middleware-stack": "^4.0.5",
+        "@smithy/node-config-provider": "^4.1.4",
+        "@smithy/node-http-handler": "^4.1.1",
+        "@smithy/protocol-http": "^5.1.3",
+        "@smithy/smithy-client": "^4.5.2",
+        "@smithy/types": "^4.3.2",
+        "@smithy/url-parser": "^4.0.5",
+        "@smithy/util-base64": "^4.0.0",
+        "@smithy/util-body-length-browser": "^4.0.0",
+        "@smithy/util-body-length-node": "^4.0.0",
+        "@smithy/util-defaults-mode-browser": "^4.0.29",
+        "@smithy/util-defaults-mode-node": "^4.0.29",
+        "@smithy/util-endpoints": "^3.0.7",
+        "@smithy/util-middleware": "^4.0.5",
+        "@smithy/util-retry": "^4.0.7",
+        "@smithy/util-utf8": "^4.0.0",
+        "@smithy/util-waiter": "^4.0.7",
+        "@types/uuid": "^9.0.1",
+        "tslib": "^2.6.2",
+        "uuid": "^9.0.1"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
       }
     },
-    "node_modules/@aws-sdk/client-sso-oidc": {
-      "version": "3.721.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/client-sso-oidc/-/client-sso-oidc-3.721.0.tgz",
-      "integrity": "sha512-jwsgdUEbNJqs1O0AQtf9M6SI7hFIjxH+IKeKCMca0xVt+Tr1UqLr/qMK/6W8LoMtRFnE0lpBSHW6hvmLp2OCoQ==",
+    "node_modules/@aws-sdk/client-ssm/node_modules/@aws-sdk/client-sso": {
+      "version": "3.886.0",
+      "resolved": "https://registry.npmjs.org/@aws-sdk/client-sso/-/client-sso-3.886.0.tgz",
+      "integrity": "sha512-CwpPZBlONsUO6OvMzNNP9PETZ3dPCQum3nUisk5VuzLTvNd80w2aWeSN/TpcAAbNvcRYbM+FsC4gBm4Q4VWn0g==",
       "license": "Apache-2.0",
       "dependencies": {
         "@aws-crypto/sha256-browser": "5.2.0",
         "@aws-crypto/sha256-js": "5.2.0",
-        "@aws-sdk/core": "3.716.0",
-        "@aws-sdk/credential-provider-node": "3.721.0",
-        "@aws-sdk/middleware-host-header": "3.714.0",
-        "@aws-sdk/middleware-logger": "3.714.0",
-        "@aws-sdk/middleware-recursion-detection": "3.714.0",
-        "@aws-sdk/middleware-user-agent": "3.721.0",
-        "@aws-sdk/region-config-resolver": "3.714.0",
-        "@aws-sdk/types": "3.714.0",
-        "@aws-sdk/util-endpoints": "3.714.0",
-        "@aws-sdk/util-user-agent-browser": "3.714.0",
-        "@aws-sdk/util-user-agent-node": "3.721.0",
-        "@smithy/config-resolver": "^3.0.13",
-        "@smithy/core": "^2.5.5",
-        "@smithy/fetch-http-handler": "^4.1.2",
-        "@smithy/hash-node": "^3.0.11",
-        "@smithy/invalid-dependency": "^3.0.11",
-        "@smithy/middleware-content-length": "^3.0.13",
-        "@smithy/middleware-endpoint": "^3.2.6",
-        "@smithy/middleware-retry": "^3.0.31",
-        "@smithy/middleware-serde": "^3.0.11",
-        "@smithy/middleware-stack": "^3.0.11",
-        "@smithy/node-config-provider": "^3.1.12",
-        "@smithy/node-http-handler": "^3.3.2",
-        "@smithy/protocol-http": "^4.1.8",
-        "@smithy/smithy-client": "^3.5.1",
-        "@smithy/types": "^3.7.2",
-        "@smithy/url-parser": "^3.0.11",
-        "@smithy/util-base64": "^3.0.0",
-        "@smithy/util-body-length-browser": "^3.0.0",
-        "@smithy/util-body-length-node": "^3.0.0",
-        "@smithy/util-defaults-mode-browser": "^3.0.31",
-        "@smithy/util-defaults-mode-node": "^3.0.31",
-        "@smithy/util-endpoints": "^2.1.7",
-        "@smithy/util-middleware": "^3.0.11",
-        "@smithy/util-retry": "^3.0.11",
-        "@smithy/util-utf8": "^3.0.0",
+        "@aws-sdk/core": "3.883.0",
+        "@aws-sdk/middleware-host-header": "3.873.0",
+        "@aws-sdk/middleware-logger": "3.876.0",
+        "@aws-sdk/middleware-recursion-detection": "3.886.0",
+        "@aws-sdk/middleware-user-agent": "3.883.0",
+        "@aws-sdk/region-config-resolver": "3.873.0",
+        "@aws-sdk/types": "3.862.0",
+        "@aws-sdk/util-endpoints": "3.879.0",
+        "@aws-sdk/util-user-agent-browser": "3.873.0",
+        "@aws-sdk/util-user-agent-node": "3.883.0",
+        "@smithy/config-resolver": "^4.1.5",
+        "@smithy/core": "^3.9.2",
+        "@smithy/fetch-http-handler": "^5.1.1",
+        "@smithy/hash-node": "^4.0.5",
+        "@smithy/invalid-dependency": "^4.0.5",
+        "@smithy/middleware-content-length": "^4.0.5",
+        "@smithy/middleware-endpoint": "^4.1.21",
+        "@smithy/middleware-retry": "^4.1.22",
+        "@smithy/middleware-serde": "^4.0.9",
+        "@smithy/middleware-stack": "^4.0.5",
+        "@smithy/node-config-provider": "^4.1.4",
+        "@smithy/node-http-handler": "^4.1.1",
+        "@smithy/protocol-http": "^5.1.3",
+        "@smithy/smithy-client": "^4.5.2",
+        "@smithy/types": "^4.3.2",
+        "@smithy/url-parser": "^4.0.5",
+        "@smithy/util-base64": "^4.0.0",
+        "@smithy/util-body-length-browser": "^4.0.0",
+        "@smithy/util-body-length-node": "^4.0.0",
+        "@smithy/util-defaults-mode-browser": "^4.0.29",
+        "@smithy/util-defaults-mode-node": "^4.0.29",
+        "@smithy/util-endpoints": "^3.0.7",
+        "@smithy/util-middleware": "^4.0.5",
+        "@smithy/util-retry": "^4.0.7",
+        "@smithy/util-utf8": "^4.0.0",
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@aws-sdk/client-ssm/node_modules/@aws-sdk/core": {
+      "version": "3.883.0",
+      "resolved": "https://registry.npmjs.org/@aws-sdk/core/-/core-3.883.0.tgz",
+      "integrity": "sha512-FmkqnqBLkXi4YsBPbF6vzPa0m4XKUuvgKDbamfw4DZX2CzfBZH6UU4IwmjNV3ZM38m0xraHarK8KIbGSadN3wg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@aws-sdk/types": "3.862.0",
+        "@aws-sdk/xml-builder": "3.873.0",
+        "@smithy/core": "^3.9.2",
+        "@smithy/node-config-provider": "^4.1.4",
+        "@smithy/property-provider": "^4.0.5",
+        "@smithy/protocol-http": "^5.1.3",
+        "@smithy/signature-v4": "^5.1.3",
+        "@smithy/smithy-client": "^4.5.2",
+        "@smithy/types": "^4.3.2",
+        "@smithy/util-base64": "^4.0.0",
+        "@smithy/util-body-length-browser": "^4.0.0",
+        "@smithy/util-middleware": "^4.0.5",
+        "@smithy/util-utf8": "^4.0.0",
+        "fast-xml-parser": "5.2.5",
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
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+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/@smithy/util-defaults-mode-node/-/util-defaults-mode-node-4.1.1.tgz",
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-        "@smithy/types": "^3.7.2",
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+        "@smithy/credential-provider-imds": "^4.1.1",
+        "@smithy/node-config-provider": "^4.2.1",
+        "@smithy/property-provider": "^4.1.1",
+        "@smithy/smithy-client": "^4.6.1",
+        "@smithy/types": "^4.5.0",
         "tslib": "^2.6.2"
       },
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-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
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+      "version": "3.1.1",
+      "resolved": "https://registry.npmjs.org/@smithy/util-endpoints/-/util-endpoints-3.1.1.tgz",
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       "license": "Apache-2.0",
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-        "@smithy/shared-ini-file-loader": "^3.1.12",
-        "@smithy/types": "^3.7.2",
+        "@smithy/node-config-provider": "^4.2.1",
+        "@smithy/types": "^4.5.0",
         "tslib": "^2.6.2"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
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-    "node_modules/@aws-sdk/credential-provider-web-identity": {
-      "version": "3.716.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/credential-provider-web-identity/-/credential-provider-web-identity-3.716.0.tgz",
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+    "node_modules/@aws-sdk/nested-clients/node_modules/@smithy/util-hex-encoding": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/@smithy/util-hex-encoding/-/util-hex-encoding-4.1.0.tgz",
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-        "@smithy/types": "^3.7.2",
         "tslib": "^2.6.2"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@aws-sdk/nested-clients/node_modules/@smithy/util-middleware": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/@smithy/util-middleware/-/util-middleware-4.1.1.tgz",
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+      "license": "Apache-2.0",
+      "dependencies": {
+        "@smithy/types": "^4.5.0",
+        "tslib": "^2.6.2"
       },
-      "peerDependencies": {
-        "@aws-sdk/client-sts": "^3.716.0"
+      "engines": {
+        "node": ">=18.0.0"
       }
     },
-    "node_modules/@aws-sdk/middleware-host-header": {
-      "version": "3.714.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/middleware-host-header/-/middleware-host-header-3.714.0.tgz",
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+    "node_modules/@aws-sdk/nested-clients/node_modules/@smithy/util-retry": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/@smithy/util-retry/-/util-retry-4.1.1.tgz",
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-        "@aws-sdk/types": "3.714.0",
-        "@smithy/protocol-http": "^4.1.8",
-        "@smithy/types": "^3.7.2",
+        "@smithy/service-error-classification": "^4.1.1",
+        "@smithy/types": "^4.5.0",
         "tslib": "^2.6.2"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
       }
     },
-    "node_modules/@aws-sdk/middleware-logger": {
-      "version": "3.714.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/middleware-logger/-/middleware-logger-3.714.0.tgz",
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+    "node_modules/@aws-sdk/nested-clients/node_modules/@smithy/util-stream": {
+      "version": "4.3.1",
+      "resolved": "https://registry.npmjs.org/@smithy/util-stream/-/util-stream-4.3.1.tgz",
+      "integrity": "sha512-khKkW/Jqkgh6caxMWbMuox9+YfGlsk9OnHOYCGVEdYQb/XVzcORXHLYUubHmmda0pubEDncofUrPNniS9d+uAA==",
       "license": "Apache-2.0",
       "dependencies": {
-        "@aws-sdk/types": "3.714.0",
-        "@smithy/types": "^3.7.2",
+        "@smithy/fetch-http-handler": "^5.2.1",
+        "@smithy/node-http-handler": "^4.2.1",
+        "@smithy/types": "^4.5.0",
+        "@smithy/util-base64": "^4.1.0",
+        "@smithy/util-buffer-from": "^4.1.0",
+        "@smithy/util-hex-encoding": "^4.1.0",
+        "@smithy/util-utf8": "^4.1.0",
         "tslib": "^2.6.2"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
       }
     },
-    "node_modules/@aws-sdk/middleware-recursion-detection": {
-      "version": "3.714.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/middleware-recursion-detection/-/middleware-recursion-detection-3.714.0.tgz",
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+    "node_modules/@aws-sdk/nested-clients/node_modules/@smithy/util-uri-escape": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/@smithy/util-uri-escape/-/util-uri-escape-4.1.0.tgz",
+      "integrity": "sha512-b0EFQkq35K5NHUYxU72JuoheM6+pytEVUGlTwiFxWFpmddA+Bpz3LgsPRIpBk8lnPE47yT7AF2Egc3jVnKLuPg==",
       "license": "Apache-2.0",
       "dependencies": {
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-        "@smithy/protocol-http": "^4.1.8",
-        "@smithy/types": "^3.7.2",
         "tslib": "^2.6.2"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
       }
     },
-    "node_modules/@aws-sdk/middleware-user-agent": {
-      "version": "3.721.0",
-      "resolved": "https://registry.npmjs.org/@aws-sdk/middleware-user-agent/-/middleware-user-agent-3.721.0.tgz",
-      "integrity": "sha512-Z3Vksb970ArsfLlARW4KVpqO+pQ1cvvGTrTQPxWDsmOzg1kU92t9oWXGW+1M/x6bHbMQlI/EulQ/D8ZE/Pu46Q==",
+    "node_modules/@aws-sdk/nested-clients/node_modules/@smithy/util-utf8": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/@smithy/util-utf8/-/util-utf8-4.1.0.tgz",
+      "integrity": "sha512-mEu1/UIXAdNYuBcyEPbjScKi/+MQVXNIuY/7Cm5XLIWe319kDrT5SizBE95jqtmEXoDbGoZxKLCMttdZdqTZKQ==",
       "license": "Apache-2.0",
       "dependencies": {
-        "@aws-sdk/core": "3.716.0",
-        "@aws-sdk/types": "3.714.0",
-        "@aws-sdk/util-endpoints": "3.714.0",
-        "@smithy/core": "^2.5.5",
-        "@smithy/protocol-http": "^4.1.8",
-        "@smithy/types": "^3.7.2",
+        "@smithy/util-buffer-from": "^4.1.0",
         "tslib": "^2.6.2"
       },
       "engines": {
-        "node": ">=16.0.0"
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@aws-sdk/nested-clients/node_modules/fast-xml-parser": {
+      "version": "5.2.5",
+      "resolved": "https://registry.npmjs.org/fast-xml-parser/-/fast-xml-parser-5.2.5.tgz",
+      "integrity": "sha512-pfX9uG9Ki0yekDHx2SiuRIyFdyAr1kMIMitPvb0YBo8SUfKvia7w7FIyd/l6av85pFYRhZscS75MwMnbvY+hcQ==",
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/NaturalIntelligence"
+        }
+      ],
+      "license": "MIT",
+      "dependencies": {
+        "strnum": "^2.1.0"
+      },
+      "bin": {
+        "fxparser": "src/cli/cli.js"
       }
     },
+    "node_modules/@aws-sdk/nested-clients/node_modules/strnum": {
+      "version": "2.1.1",
+      "resolved": "https://registry.npmjs.org/strnum/-/strnum-2.1.1.tgz",
+      "integrity": "sha512-7ZvoFTiCnGxBtDqJ//Cu6fWtZtc7Y3x+QOirG15wztbdngGSkht27o2pyGWrVy0b4WAy3jbKmnoK6g5VlVNUUw==",
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/NaturalIntelligence"
+        }
+      ],
+      "license": "MIT"
+    },
     "node_modules/@aws-sdk/region-config-resolver": {
       "version": "3.714.0",
       "resolved": "https://registry.npmjs.org/@aws-sdk/region-config-resolver/-/region-config-resolver-3.714.0.tgz",
@@ -684,6 +2533,40 @@
         }
       }
     },
+    "node_modules/@aws-sdk/xml-builder": {
+      "version": "3.873.0",
+      "resolved": "https://registry.npmjs.org/@aws-sdk/xml-builder/-/xml-builder-3.873.0.tgz",
+      "integrity": "sha512-kLO7k7cGJ6KaHiExSJWojZurF7SnGMDHXRuQunFnEoD0n1yB6Lqy/S/zHiQ7oJnBhPr9q0TW9qFkrsZb1Uc54w==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@smithy/types": "^4.3.2",
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@aws-sdk/xml-builder/node_modules/@smithy/types": {
+      "version": "4.5.0",
+      "resolved": "https://registry.npmjs.org/@smithy/types/-/types-4.5.0.tgz",
+      "integrity": "sha512-RkUpIOsVlAwUIZXO1dsz8Zm+N72LClFfsNqf173catVlvRZiwPy0x2u0JLEA4byreOPKDZPGjmPDylMoP8ZJRg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@aws/lambda-invoke-store": {
+      "version": "0.0.1",
+      "resolved": "https://registry.npmjs.org/@aws/lambda-invoke-store/-/lambda-invoke-store-0.0.1.tgz",
+      "integrity": "sha512-ORHRQ2tmvnBXc8t/X9Z8IcSbBA4xTLKuN873FopzklHMeqBst7YG0d+AX97inkvDX+NChYtSr+qGfcqGFaI8Zw==",
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
     "node_modules/@smithy/abort-controller": {
       "version": "3.1.9",
       "resolved": "https://registry.npmjs.org/@smithy/abort-controller/-/abort-controller-3.1.9.tgz",
@@ -1237,6 +3120,45 @@
         "node": ">=16.0.0"
       }
     },
+    "node_modules/@smithy/util-waiter": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/@smithy/util-waiter/-/util-waiter-4.1.1.tgz",
+      "integrity": "sha512-PJBmyayrlfxM7nbqjomF4YcT1sApQwZio0NHSsT0EzhJqljRmvhzqZua43TyEs80nJk2Cn2FGPg/N8phH6KeCQ==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@smithy/abort-controller": "^4.1.1",
+        "@smithy/types": "^4.5.0",
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@smithy/util-waiter/node_modules/@smithy/abort-controller": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/@smithy/abort-controller/-/abort-controller-4.1.1.tgz",
+      "integrity": "sha512-vkzula+IwRvPR6oKQhMYioM3A/oX/lFCZiwuxkQbRhqJS2S4YRY2k7k/SyR2jMf3607HLtbEwlRxi0ndXHMjRg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@smithy/types": "^4.5.0",
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
+    "node_modules/@smithy/util-waiter/node_modules/@smithy/types": {
+      "version": "4.5.0",
+      "resolved": "https://registry.npmjs.org/@smithy/types/-/types-4.5.0.tgz",
+      "integrity": "sha512-RkUpIOsVlAwUIZXO1dsz8Zm+N72LClFfsNqf173catVlvRZiwPy0x2u0JLEA4byreOPKDZPGjmPDylMoP8ZJRg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "tslib": "^2.6.2"
+      },
+      "engines": {
+        "node": ">=18.0.0"
+      }
+    },
     "node_modules/@types/aws-lambda": {
       "version": "8.10.147",
       "resolved": "https://registry.npmjs.org/@types/aws-lambda/-/aws-lambda-8.10.147.tgz",
diff --git a/lib/database/lambda/package.json b/lib/database/lambda/package.json
index b540bd0a..396adadf 100644
--- a/lib/database/lambda/package.json
+++ b/lib/database/lambda/package.json
@@ -2,7 +2,8 @@
   "name": "pgbouncer-secret-updater",
   "version": "1.0.0",
   "dependencies": {
-    "@aws-sdk/client-secrets-manager": "^3.0.0"
+    "@aws-sdk/client-secrets-manager": "^3.0.0",
+    "@aws-sdk/client-ssm": "^3.0.0"
   },
   "devDependencies": {
     "@types/aws-lambda": "^8.10.0",
diff --git a/lib/database/lambda/pgbouncer-health-check/health-check.sh b/lib/database/lambda/pgbouncer-health-check/health-check.sh
new file mode 100644
index 00000000..1ad1fce0
--- /dev/null
+++ b/lib/database/lambda/pgbouncer-health-check/health-check.sh
@@ -0,0 +1,135 @@
+#!/bin/bash
+set -euo pipefail
+
+echo '=== PGBOUNCER HEALTH CHECK START ==='
+echo 'Health check started at:' $(date)
+echo ''
+
+# Wait for cloud-init to complete before checking pgbouncer
+echo '=== WAITING: Cloud-init completion check ==='
+MAX_WAIT=300  # 5 minutes max wait
+WAIT_COUNT=0
+while [ $WAIT_COUNT -lt $MAX_WAIT ]; do
+  if command -v cloud-init >/dev/null 2>&1; then
+    CLOUD_INIT_STATUS=$(cloud-init status --format=json 2>/dev/null | grep '"status":' | sed 's/.*"status": *"\([^"]*\)".*/\1/' 2>/dev/null)
+    echo "Cloud-init status: $CLOUD_INIT_STATUS (waited ${WAIT_COUNT}s)"
+    if [ "$CLOUD_INIT_STATUS" = "done" ]; then
+      echo 'SUCCESS: Cloud-init has completed'
+      break
+    elif [ "$CLOUD_INIT_STATUS" = "error" ]; then
+      echo 'CLOUD-INIT SETUP FAILED:'
+      cloud-init status --long 2>&1 || true
+      echo ''
+      echo 'Setup script errors:'
+      tail -n 20 /var/log/cloud-init-output.log 2>&1 || echo 'Could not read setup logs'
+      exit 1
+    fi
+  else
+    echo 'Cloud-init command not available, assuming setup is complete'
+    break
+  fi
+
+  if [ $WAIT_COUNT -eq 0 ]; then
+    echo 'Cloud-init is still running, waiting for completion...'
+  fi
+
+  sleep 10
+  WAIT_COUNT=$((WAIT_COUNT + 10))
+done
+
+if [ $WAIT_COUNT -ge $MAX_WAIT ]; then
+  echo 'WARNING: Timed out waiting for cloud-init to complete after 10 minutes'
+  echo 'Current cloud-init status:'
+  cloud-init status --long || true
+  echo 'Proceeding with health check anyway...'
+fi
+
+echo 'Cloud-init wait complete, now checking pgbouncer...'
+echo ''
+
+# Critical check: Verify pgbouncer service is active
+echo '=== CRITICAL: PgBouncer service status ==='
+if systemctl is-active --quiet pgbouncer; then
+  echo 'SUCCESS: PgBouncer service is active'
+  systemctl status pgbouncer --no-pager --lines=5
+else
+  echo 'FAILURE: PgBouncer service is NOT active'
+  echo 'Service status:'
+  systemctl status pgbouncer --no-pager --lines=10 || echo 'Could not get service status'
+  echo 'Service is-active result:' $(systemctl is-active pgbouncer)
+  echo 'Service is-enabled result:' $(systemctl is-enabled pgbouncer)
+  echo 'Last 20 lines of pgbouncer systemd logs:'
+  journalctl -u pgbouncer --no-pager -n 20 || echo 'Could not get pgbouncer logs'
+  echo ''
+  echo '=== SETUP DIAGNOSTICS: Cloud-init output log ==='
+  if [ -f /var/log/cloud-init-output.log ]; then
+    echo 'Last 50 lines of cloud-init-output.log to help diagnose setup issues:'
+    tail -n 50 /var/log/cloud-init-output.log
+  else
+    echo 'Cloud-init-output.log not found'
+  fi
+  echo ''
+  echo '=== SETUP DIAGNOSTICS: Cloud-init status ==='
+  if command -v cloud-init >/dev/null 2>&1; then
+    cloud-init status --long || echo 'Could not get cloud-init status'
+  else
+    echo 'cloud-init command not available'
+  fi
+  exit 1
+fi
+
+# Critical check: Verify pgbouncer is listening on port 5432
+echo '=== CRITICAL: Network listening check ==='
+if ss -tlnp | grep -q ':5432.*pgbouncer' || netstat -tlnp 2>/dev/null | grep -q ':5432.*pgbouncer'; then
+  echo 'SUCCESS: PgBouncer is listening on port 5432'
+  ss -tlnp | grep :5432 | head -3 2>/dev/null || netstat -tlnp 2>/dev/null | grep :5432 | head -3
+else
+  echo 'FAILURE: PgBouncer is NOT listening on port 5432'
+  echo 'All processes listening on 5432:'
+  ss -tlnp | grep :5432 2>/dev/null || netstat -tlnp 2>/dev/null | grep :5432 || echo 'No processes listening on port 5432'
+  echo 'All pgbouncer processes:'
+  ps aux | grep pgbouncer | grep -v grep || echo 'No pgbouncer processes running'
+  exit 1
+fi
+
+# Critical check: Test TCP connection to pgbouncer
+echo '=== CRITICAL: Connection test ==='
+if timeout 10 bash -c "</dev/tcp/localhost/5432"; then
+  echo 'SUCCESS: TCP connection to localhost:5432 successful'
+else
+  echo 'FAILURE: TCP connection to localhost:5432 failed'
+  echo 'Connection test failed - pgbouncer may not be responding'
+  exit 1
+fi
+
+# Detailed diagnostics (only if basic checks pass)
+echo '=== DIAGNOSTICS: Additional information ==='
+echo 'System uptime:' $(uptime)
+
+# Check pgbouncer configuration
+if [ -f /etc/pgbouncer/pgbouncer.ini ]; then
+  echo 'PgBouncer config exists:'
+  ls -la /etc/pgbouncer/pgbouncer.ini
+  echo 'Key config settings:'
+  grep -E '^(listen_|pool_mode|max_|default_pool_size)' /etc/pgbouncer/pgbouncer.ini | head -10
+else
+  echo 'WARNING: PgBouncer config not found'
+fi
+
+# Check pgbouncer logs for recent activity
+if [ -f /var/log/pgbouncer/pgbouncer.log ]; then
+  echo 'Recent pgbouncer log entries (last 10 lines):'
+  tail -n 10 /var/log/pgbouncer/pgbouncer.log
+else
+  echo 'PgBouncer log not found'
+fi
+
+# Check if setup is still running (should be done by now)
+if pgrep -af cloud-init > /dev/null || pgrep -af 'pgbouncer.*setup' > /dev/null; then
+  echo 'WARNING: Setup processes still running - this may indicate setup incomplete'
+  ps aux | grep -E '(cloud-init|setup)' | grep -v grep || true
+fi
+
+echo '=== SUCCESS: All critical checks passed ==='
+echo 'PgBouncer is running and accessible on port 5432'
+echo 'Health check completed at:' $(date)
diff --git a/lib/database/lambda/pgbouncer-health-check/index.ts b/lib/database/lambda/pgbouncer-health-check/index.ts
new file mode 100644
index 00000000..4ed5cd5c
--- /dev/null
+++ b/lib/database/lambda/pgbouncer-health-check/index.ts
@@ -0,0 +1,321 @@
+import {
+  SSMClient,
+  SendCommandCommand,
+  GetCommandInvocationCommand,
+  DescribeInstanceInformationCommand,
+} from "@aws-sdk/client-ssm";
+import { CloudFormationCustomResourceEvent, Context } from "aws-lambda";
+import * as https from "https";
+import * as url from "url";
+import * as fs from "fs";
+import * as path from "path";
+
+const ssmClient = new SSMClient();
+
+interface ResponseData {
+  Message?: string;
+  Output?: string;
+  Reason?: string;
+}
+
+interface HealthCheckResult {
+  success: boolean;
+  output?: string;
+  error?: string;
+}
+
+const sleep = (ms: number): Promise<void> =>
+  new Promise((resolve) => setTimeout(resolve, ms));
+
+async function sendResponse(
+  event: CloudFormationCustomResourceEvent,
+  context: Context,
+  responseStatus: "SUCCESS" | "FAILED",
+  responseData: ResponseData,
+  physicalResourceId?: string
+): Promise<void> {
+  const responseBody = JSON.stringify({
+    Status: responseStatus,
+    Reason:
+      responseData.Reason ||
+      `See CloudWatch Log Stream: ${context.logStreamName}`,
+    PhysicalResourceId: physicalResourceId || context.logStreamName,
+    StackId: event.StackId,
+    RequestId: event.RequestId,
+    LogicalResourceId: event.LogicalResourceId,
+    Data: responseData,
+  });
+
+  const parsedUrl = url.parse(event.ResponseURL);
+
+  return new Promise((resolve, reject) => {
+    const options = {
+      hostname: parsedUrl.hostname,
+      port: 443,
+      path: parsedUrl.path,
+      method: "PUT",
+      headers: {
+        "Content-Type": "",
+        "Content-Length": responseBody.length,
+      },
+    };
+
+    const req = https.request(options, (res) => {
+      console.log(`STATUS: ${res.statusCode}`);
+      console.log(`HEADERS: ${JSON.stringify(res.headers)}`);
+      resolve();
+    });
+
+    req.on("error", (err) => {
+      console.log("sendResponse Error:", err);
+      reject(err);
+    });
+
+    req.write(responseBody);
+    req.end();
+  });
+}
+
+async function waitForInstanceReady(
+  instanceId: string,
+  maxWaitMinutes: number = 8
+): Promise<boolean> {
+  console.log(
+    `Waiting for instance ${instanceId} to be ready for SSM commands...`
+  );
+  const maxAttempts = maxWaitMinutes * 4; // Check every 15 seconds
+
+  for (let attempt = 1; attempt <= maxAttempts; attempt++) {
+    try {
+      const command = new DescribeInstanceInformationCommand({
+        InstanceInformationFilterList: [
+          {
+            key: "InstanceIds",
+            valueSet: [instanceId],
+          },
+        ],
+      });
+
+      const result = await ssmClient.send(command);
+
+      if (
+        result.InstanceInformationList &&
+        result.InstanceInformationList.length > 0
+      ) {
+        const instance = result.InstanceInformationList[0];
+        if (instance.PingStatus === "Online") {
+          console.log(
+            `Instance ${instanceId} is online and ready for SSM commands`
+          );
+          return true;
+        }
+        console.log(
+          `Instance ${instanceId} ping status: ${instance.PingStatus}, attempt ${attempt}/${maxAttempts}`
+        );
+      } else {
+        console.log(
+          `Instance ${instanceId} not found in SSM, attempt ${attempt}/${maxAttempts}`
+        );
+      }
+    } catch (error) {
+      const errorMessage =
+        error instanceof Error ? error.message : "Unknown error";
+      console.log(
+        `Error checking instance readiness (attempt ${attempt}/${maxAttempts}):`,
+        errorMessage
+      );
+    }
+
+    if (attempt < maxAttempts) {
+      await sleep(15000); // Wait 15 seconds between attempts
+    }
+  }
+
+  throw new Error(
+    `Instance ${instanceId} did not become ready for SSM commands within ${maxWaitMinutes} minutes`
+  );
+}
+
+async function checkPgBouncerHealth(
+  instanceId: string
+): Promise<HealthCheckResult> {
+  console.log(`Running health check on instance ${instanceId}`);
+
+  // Load health check script from file
+  const scriptPath = path.join(__dirname, "health-check.sh");
+  let healthCheckScript: string;
+
+  try {
+    healthCheckScript = fs.readFileSync(scriptPath, "utf8");
+  } catch (error) {
+    console.error("Failed to load health check script:", error);
+    return {
+      success: false,
+      error: `Failed to load health check script: ${error}`,
+    };
+  }
+
+  // Use the entire script as a single command
+  const healthCheckCommands = [healthCheckScript];
+
+  const command = new SendCommandCommand({
+    InstanceIds: [instanceId],
+    DocumentName: "AWS-RunShellScript",
+    Parameters: {
+      commands: healthCheckCommands,
+      executionTimeout: ["600"], // 10 minutes timeout
+    },
+    Comment: "PgBouncer comprehensive health check with setup validation",
+    TimeoutSeconds: 600,
+  });
+
+  try {
+    console.log("Sending SSM command...");
+    const result = await ssmClient.send(command);
+    const commandId = result.Command?.CommandId;
+
+    if (!commandId) {
+      return {
+        success: false,
+        error: "Failed to get command ID from SSM response",
+      };
+    }
+
+    console.log(`Command sent with ID: ${commandId}`);
+
+    // Wait for command to complete
+    const maxAttempts = 60; // 10 minutes with 10-second intervals
+    for (let attempt = 1; attempt <= maxAttempts; attempt++) {
+      await sleep(10000); // Wait 10 seconds between status checks
+
+      try {
+        const invocationCommand = new GetCommandInvocationCommand({
+          CommandId: commandId,
+          InstanceId: instanceId,
+        });
+
+        const invocation = await ssmClient.send(invocationCommand);
+
+        console.log(
+          `Command status (attempt ${attempt}): ${invocation.Status}`
+        );
+
+        if (invocation.Status === "Success") {
+          console.log("Health check passed!");
+          console.log("STDOUT:", invocation.StandardOutputContent);
+          return {
+            success: true,
+            output: invocation.StandardOutputContent,
+          };
+        } else if (invocation.Status === "Failed") {
+          console.log("Health check failed!");
+          console.log("STDOUT:", invocation.StandardOutputContent);
+          console.log("STDERR:", invocation.StandardErrorContent);
+          return {
+            success: false,
+            error: `Health check failed: ${invocation.StandardErrorContent}`,
+            output: invocation.StandardOutputContent,
+          };
+        } else if (
+          ["Cancelled", "TimedOut", "Cancelling"].includes(
+            invocation.Status || ""
+          )
+        ) {
+          return {
+            success: false,
+            error: `Health check ${invocation.Status?.toLowerCase()}`,
+          };
+        }
+        // Continue waiting for InProgress, Pending, Delayed states
+      } catch (error: any) {
+        if (error.name === "InvocationDoesNotExist") {
+          console.log(
+            `Command invocation not yet available (attempt ${attempt})`
+          );
+          continue;
+        }
+        throw error;
+      }
+    }
+
+    return {
+      success: false,
+      error: "Health check timed out waiting for command completion",
+    };
+  } catch (error) {
+    const errorMessage =
+      error instanceof Error ? error.message : "Unknown error";
+    console.log("Error running health check:", error);
+    return {
+      success: false,
+      error: `Health check error: ${errorMessage}`,
+    };
+  }
+}
+
+export const handler = async (
+  event: CloudFormationCustomResourceEvent,
+  context: Context
+): Promise<void> => {
+  console.log("Event:", JSON.stringify(event, null, 2));
+
+  const instanceId = event.ResourceProperties?.InstanceId;
+  const requestType = event.RequestType;
+
+  try {
+    if (requestType === "Delete") {
+      console.log("Delete request - no action needed");
+      await sendResponse(event, context, "SUCCESS", {});
+      return;
+    }
+
+    if (!instanceId) {
+      throw new Error("InstanceId is required");
+    }
+
+    console.log(`Processing ${requestType} request for instance ${instanceId}`);
+
+    // Wait for instance to be ready for SSM
+    await waitForInstanceReady(instanceId);
+
+    // Run health check
+    const healthResult = await checkPgBouncerHealth(instanceId);
+
+    if (healthResult.success) {
+      console.log("PgBouncer health check passed");
+      await sendResponse(
+        event,
+        context,
+        "SUCCESS",
+        {
+          Message: "PgBouncer is healthy",
+        },
+        `pgbouncer-health-${instanceId}`
+      );
+    } else {
+      console.log("PgBouncer health check failed:", healthResult.error);
+      await sendResponse(
+        event,
+        context,
+        "FAILED",
+        {
+          Reason: `PgBouncer health check failed: ${healthResult.error}`,
+        },
+        `pgbouncer-health-${instanceId}`
+      );
+    }
+  } catch (error) {
+    const errorMessage =
+      error instanceof Error ? error.message : "Unknown error occurred";
+    console.log("Handler error:", error);
+    await sendResponse(
+      event,
+      context,
+      "FAILED",
+      {
+        Reason: errorMessage,
+      },
+      `pgbouncer-health-${instanceId || "unknown"}`
+    );
+  }
+};
diff --git a/lib/database/pgbouncer-setup.sh b/lib/database/pgbouncer-setup.sh
index ed5d5f94..e0274518 100644
--- a/lib/database/pgbouncer-setup.sh
+++ b/lib/database/pgbouncer-setup.sh
@@ -14,26 +14,46 @@ MAX_DB_CONNECTIONS=${MAX_DB_CONNECTIONS}
 MAX_USER_CONNECTIONS=${MAX_USER_CONNECTIONS}
 CLOUDWATCH_CONFIG="/opt/aws/amazon-cloudwatch-agent/bin/config.json"
 
-# Add the postgres repository
-curl https://www.postgresql.org/media/keys/ACCC4CF8.asc | sudo apt-key add -
-sudo sh -c 'echo "deb http://apt.postgresql.org/pub/repos/apt $(lsb_release -cs)-pgdg main" > /etc/apt/sources.list.d/pgdg.list'
+wait_for_dpkg_lock() {
+    local max_wait=300
+    local elapsed=0
 
-# Install required packages
+    while [ $elapsed -lt $max_wait ]; do
+        if ! fuser /var/lib/dpkg/lock-frontend /var/lib/dpkg/lock 2>/dev/null; then
+            echo "dpkg locks are free, proceeding..."
+            return 0
+        fi
 
-# Function that makes sure we don't hit a dpkg lock error
-wait_for_dpkg_lock() {
-  while fuser /var/lib/dpkg/lock-frontend /var/lib/dpkg/lock >/dev/null 2>&1; do
-    echo "Waiting for dpkg lock to be released..."
-    sleep 2
-  done
+        echo "Waiting for dpkg locks... (${elapsed}s elapsed)"
+        fuser -v /var/lib/dpkg/lock-frontend /var/lib/dpkg/lock 2>/dev/null || true
+
+        sleep 5
+        elapsed=$((elapsed + 5))
+    done
+
+    echo "ERROR: Timeout waiting for dpkg locks after ${max_wait} seconds"
+    return 1
 }
 
-wait_for_dpkg_lock
+if systemctl is-active --quiet unattended-upgrades 2>/dev/null; then
+    echo "Stopping unattended-upgrades service temporarily..."
+    systemctl stop unattended-upgrades
+fi
+
 export DEBIAN_FRONTEND=noninteractive
 
+curl -fsSL https://www.postgresql.org/media/keys/ACCC4CF8.asc | gpg --dearmor -o /etc/apt/trusted.gpg.d/postgresql.gpg
+echo "deb http://apt.postgresql.org/pub/repos/apt $(lsb_release -cs)-pgdg main" > /etc/apt/sources.list.d/pgdg.list
+
+wait_for_dpkg_lock
 apt-get update
+
+wait_for_dpkg_lock
 apt-get upgrade -y
+
+wait_for_dpkg_lock
 apt-get install -y pgbouncer jq
+
 snap install aws-cli --classic
 
 echo "Fetching secret from ARN: ${SECRET_ARN}"
@@ -112,7 +132,6 @@ chmod 640 /var/log/pgbouncer/pgbouncer.log
 systemctl enable pgbouncer
 systemctl restart pgbouncer
 
-
 cat <<EOC > /etc/logrotate.d/pgbouncer
 /var/log/pgbouncer/pgbouncer.log {
     daily
@@ -172,6 +191,7 @@ if ! wget -q https://s3.amazonaws.com/amazoncloudwatch-agent/ubuntu/amd64/latest
   exit 1
 fi
 
+wait_for_dpkg_lock
 if ! dpkg -i amazon-cloudwatch-agent.deb; then
   echo 'Failed to install CloudWatch agent' | logger -t pgbouncer-setup
   exit 1
@@ -259,3 +279,98 @@ if ! systemctl is-active amazon-cloudwatch-agent; then
   echo 'CloudWatch agent failed to start' | logger -t pgbouncer-setup
   exit 1
 fi
+
+# Configure unattended-upgrades for security updates on this long-lived instance
+echo "Configuring unattended-upgrades for security updates..."
+
+# Create optimized unattended-upgrades configuration
+cat > /etc/apt/apt.conf.d/50unattended-upgrades << 'EOF'
+// Automatically upgrade packages from these origins
+Unattended-Upgrade::Allowed-Origins {
+    "${distro_id}:${distro_codename}-security";
+    "${distro_id}ESMApps:${distro_codename}-apps-security";
+    "${distro_id}ESM:${distro_codename}-infra-security";
+    // Add PostgreSQL security updates
+    "apt.postgresql.org:${distro_codename}-pgdg main";
+};
+
+// Do not automatically upgrade these packages - keep manual control
+Unattended-Upgrade::Package-Blacklist {
+    "pgbouncer";
+    "postgresql*";
+    "libpq*";
+};
+
+// Automatically reboot if required after security updates
+// Only during maintenance window
+Unattended-Upgrade::Automatic-Reboot "true";
+Unattended-Upgrade::Automatic-Reboot-Time "02:00";
+
+// Remove unused automatically installed kernel-related packages
+Unattended-Upgrade::Remove-Unused-Kernel-Packages "true";
+
+// Remove unused dependencies
+Unattended-Upgrade::Remove-Unused-Dependencies "true";
+
+// Automatically remove new unused dependencies after the upgrade
+Unattended-Upgrade::Remove-New-Unused-Dependencies "true";
+
+// Split the upgrade into the smallest possible chunks
+Unattended-Upgrade::MinimalSteps "true";
+
+// Install updates in the background
+Unattended-Upgrade::InstallOnShutdown "false";
+EOF
+
+# Configure automatic update schedule
+cat > /etc/apt/apt.conf.d/20auto-upgrades << 'EOF'
+// Enable automatic updates
+APT::Periodic::Update-Package-Lists "1";
+APT::Periodic::Unattended-Upgrade "1";
+
+// Download upgradeable packages
+APT::Periodic::Download-Upgradeable-Packages "1";
+
+// Clean local download archive
+APT::Periodic::AutocleanInterval "7";
+
+// Verbose logging for debugging
+APT::Periodic::Verbose "2";
+EOF
+
+# Configure systemd timer for predictable timing
+mkdir -p /etc/systemd/system/apt-daily.timer.d/
+mkdir -p /etc/systemd/system/apt-daily-upgrade.timer.d/
+
+cat > /etc/systemd/system/apt-daily.timer.d/override.conf << 'EOF'
+[Timer]
+# Run at 1 AM daily instead of random times
+OnCalendar=
+OnCalendar=01:00
+RandomizedDelaySec=0
+EOF
+
+cat > /etc/systemd/system/apt-daily-upgrade.timer.d/override.conf << 'EOF'
+[Timer]
+# Run upgrades at 1:30 AM, after the update check
+OnCalendar=
+OnCalendar=01:30
+RandomizedDelaySec=0
+EOF
+
+# Reload systemd and re-enable unattended-upgrades
+systemctl daemon-reload
+systemctl enable unattended-upgrades
+systemctl start unattended-upgrades
+
+# Enable and configure the timers
+systemctl enable apt-daily.timer
+systemctl enable apt-daily-upgrade.timer
+
+echo "Setup complete!"
+echo "- PgBouncer: configured and running"
+echo "- CloudWatch: monitoring enabled"
+echo "- Security updates: enabled (daily at 1:00-1:30 AM)"
+echo "- Auto-reboot: enabled at 2:00 AM if required"
+echo "- PgBouncer packages: protected from auto-updates"
+echo "- Health monitoring: running every minute via cron"