diff --git a/.ci/scripts/generate_skills.sh b/.ci/scripts/generate_skills.sh
new file mode 100755
index 0000000..7aae9d4
--- /dev/null
+++ b/.ci/scripts/generate_skills.sh
@@ -0,0 +1,122 @@
+#!/bin/bash
+set -e
+
+# Ensure VERSION is passed from the environment
+if [ -z "$VERSION" ]; then
+  echo "Error: VERSION environment variable is not set."
+  exit 1
+fi
+
+# SKILL CONFIGURATION
+# Format: "toolset" "description"
+# The skill name is automatically generated as "cloud-sql-postgres-<toolset>"
+SKILLS=(
+  "admin"
+  "Use these skills when you need to provision new Cloud SQL instances, create databases and users, clone existing environments, and monitor the progress of long-running operations."
+
+  "lifecycle"
+  "Use these skills when you need to manage the lifecycle of your instances, including performing backups and restores, checking major version upgrade compatibility, and monitoring overall instance status."
+
+  "data"
+  "Use these skills when you need to explore the database structure, discover schema objects like views or stored procedures, and execute custom SQL queries to interact with your data."
+
+  "health"
+  "Use these skills when you need to audit database health, identify storage bloat, find invalid indexes, analyze table statistics, and manage maintenance configurations like autovacuum."
+
+  "monitor"
+  "Use these skills when you need to troubleshoot performance bottlenecks, analyze query execution plans, identify resource-heavy processes, and monitor system-level PromQL metrics."
+
+  "view-config"
+  "Use these skills when you need to discover and manage PostgreSQL extensions or fine-tune engine-level settings such as memory allocation and server configuration parameters."
+
+  "replication"
+  "Use these skills when you need to monitor replication health, manage sync states between nodes, and audit database roles and security settings to ensure environment integrity."
+
+  "vectorassist"
+  "Use these skills to set up and optimize production-ready vector workloads by simply expressing your intent and performance requirements"
+)
+
+echo "VALIDATING TOOLSETS BEFORE GENERATION"
+
+# Dynamically build the SUPPORTED_TOOLSETS array from the SKILLS array.
+# We use 'set --' to process the array in chunks without index arithmetic.
+SUPPORTED_TOOLSETS=()
+set -- "${SKILLS[@]}"
+while [ $# -gt 0 ]; do
+  SUPPORTED_TOOLSETS+=("$1")
+  shift 2
+done
+
+echo "Currently Supported Toolsets: ${SUPPORTED_TOOLSETS[*]}"
+
+# Fetch the upstream source of truth YAML for this specific version
+RAW_URL="https://raw.githubusercontent.com/googleapis/mcp-toolbox/v${VERSION}/internal/prebuiltconfigs/tools/cloud-sql-postgres.yaml"
+echo "Fetching upstream config from: $RAW_URL"
+UPSTREAM_YAML=$(curl -sL --fail "$RAW_URL" || { echo "Error: Could not fetch upstream YAML for v$VERSION"; exit 1; })
+
+# Extract the list of toolsets
+UPSTREAM_TOOLSETS=$(echo "$UPSTREAM_YAML" | awk '/^toolsets:/{flag=1; next} flag && /^  [a-zA-Z0-9_-]+:/{print $1}' | sed 's/://g')
+
+# Compare upstream toolsets against our supported list
+MISSING_TOOLSETS=false
+
+for upstream_tool in $UPSTREAM_TOOLSETS; do
+  if [ -z "$upstream_tool" ] || [ "$upstream_tool" == "-" ]; then continue; fi
+
+  if [[ ! " ${SUPPORTED_TOOLSETS[*]} " =~ " ${upstream_tool} " ]]; then
+    echo "ERROR: Upstream configuration contains a new toolset: '$upstream_tool'"
+    MISSING_TOOLSETS=true
+  fi
+done
+
+if [ "$MISSING_TOOLSETS" = true ]; then
+  echo "PIPELINE FAILED: Missing Toolset Generators"
+  echo "The source of truth file has toolsets that your script does not support."
+  echo "Please update the SKILLS array in generate_skills.sh to include generators"
+  echo "for the missing toolsets above, then commit your changes to unblock this PR."
+  exit 1
+fi
+
+echo "Validation passed. All upstream toolsets are supported."
+
+echo "BEGINNING SKILL GENERATION"
+
+LICENSE_HEADER="// Copyright 2026 Google LLC
+//
+// Licensed under the Apache License, Version 2.0 (the \"License\");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//      http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an \"AS IS\" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License."
+
+ADDITIONAL_NOTES="Note: The scripts automatically load the environment variables from various .env files. Do not ask the user to set vars unless skill executions fails due to env var absence."
+
+# Base Command Function
+generate_skill() {
+  local TOOLSET="$1"
+  local SKILL_DESC="$2"
+  local SKILL_NAME="cloud-sql-postgres-$TOOLSET"
+
+  echo "Generating skill: $SKILL_NAME..."
+  
+  npx "@toolbox-sdk/server@${VERSION}" --prebuilt cloud-sql-postgres skills-generate \
+    --name "$SKILL_NAME" \
+    --description "$SKILL_DESC" \
+    --toolset="$TOOLSET" \
+    --license-header "$LICENSE_HEADER" \
+    --additional-notes="$ADDITIONAL_NOTES"
+}
+
+set -- "${SKILLS[@]}"
+while [ $# -gt 0 ]; do
+  generate_skill "$1" "$2"
+  shift 2
+done
+
+echo "All skills generated successfully!"
diff --git a/.ci/skills-gen.cloudbuild.yaml b/.ci/skills-gen.cloudbuild.yaml
new file mode 100644
index 0000000..977f994
--- /dev/null
+++ b/.ci/skills-gen.cloudbuild.yaml
@@ -0,0 +1,99 @@
+# Copyright 2026 Google LLC
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+steps:
+  - id: "setup-ssh"
+    name: "gcr.io/cloud-builders/git"
+    entrypoint: "bash"
+    secretEnv:
+      - "GITHUB_TOKEN"
+    volumes:
+      - name: "ssh-keys"
+        path: /root/.ssh
+    args:
+      - -c
+      - |
+        # Write the secret key to the shared volume and secure it
+        printf "%s\n" "$$GITHUB_TOKEN" > /root/.ssh/id_ed25519
+        chmod 400 /root/.ssh/id_ed25519
+
+        # Scan GitHub's server to prevent interactive prompts
+        ssh-keyscan -t rsa github.com > /root/.ssh/known_hosts
+
+  - id: "generate-skills"
+    name: "node:20"
+    waitFor: ["setup-ssh"]
+    entrypoint: "bash"
+    env:
+      - "CLOUD_SQL_POSTGRES_PROJECT=$PROJECT_ID"
+      - "CLOUD_SQL_POSTGRES_INSTANCE=$_CLOUD_SQL_POSTGRES_INSTANCE"
+      - "CLOUD_SQL_POSTGRES_DATABASE=$_DATABASE_NAME"
+      - "CLOUD_SQL_POSTGRES_REGION=$_REGION"
+    secretEnv:
+      - "CLOUD_SQL_POSTGRES_USER"
+      - "CLOUD_SQL_POSTGRES_PASSWORD"
+    args:
+      - -c
+      - |
+        export VERSION=$$(cat toolbox_version.txt | tr -d '\n')
+        echo "Detected toolbox version: $$VERSION"
+
+        chmod +x ./.ci/scripts/generate_skills.sh
+        ./.ci/scripts/generate_skills.sh
+
+  - id: "commit-and-push"
+    name: "gcr.io/cloud-builders/git"
+    waitFor: ["generate-skills"]
+    entrypoint: "bash"
+    volumes:
+      - name: "ssh-keys"
+        path: /root/.ssh
+    args:
+      - -c
+      - |
+        git config --global --add safe.directory '*'
+
+        if [ -z "$$(git status --porcelain)" ]; then
+          echo "No new files generated. Exiting without committing."
+          exit 0
+        fi
+
+        echo "Changes detected. Preparing to commit..."
+        git config user.name "release-please[bot]"
+        git config user.email "55107282+release-please[bot]@users.noreply.github.com"
+
+        git remote set-url origin git@github.com:gemini-cli-extensions/cloud-sql-postgresql.git
+        git add .
+        git commit -m "chore: auto-generate skills based on toolbox_version.txt update"
+        git push origin HEAD:$_HEAD_BRANCH
+
+availableSecrets:
+  secretManager:
+    - versionName: projects/$PROJECT_ID/secrets/cloud_sql_pg_user/versions/latest
+      env: "CLOUD_SQL_POSTGRES_USER"
+    - versionName: projects/$PROJECT_ID/secrets/cloud_sql_pg_pass/versions/latest
+      env: "CLOUD_SQL_POSTGRES_PASSWORD"
+    - versionName: projects/$PROJECT_ID/secrets/github_token_cloud_sql_postgresql/versions/latest
+      env: "GITHUB_TOKEN"
+
+options:
+  logging: CLOUD_LOGGING_ONLY
+  automapSubstitutions: true
+  substitutionOption: "ALLOW_LOOSE"
+  dynamicSubstitutions: true
+
+substitutions:
+  _DATABASE_NAME: "test_database"
+  _REGION: "us-central1"
+  _CLOUD_SQL_POSTGRES_INSTANCE: "cloud-sql-pg-testing"