diff --git a/.github/scripts/generate_skills.sh b/.github/scripts/generate_skills.sh
new file mode 100755
index 0000000..8b17916
--- /dev/null
+++ b/.github/scripts/generate_skills.sh
@@ -0,0 +1,124 @@
+#!/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. Each toolset is its own YAML document:
+#   kind: toolset
+#   name: <toolset>
+UPSTREAM_TOOLSETS=$(echo "$UPSTREAM_YAML" | awk '$1=="kind:" && $2=="toolset"{f=1; next} f && $1=="name:"{print $2; f=0}')
+
+# 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/.github/workflows/skills-generate.yml b/.github/workflows/skills-generate.yml
new file mode 100644
index 0000000..e31c015
--- /dev/null
+++ b/.github/workflows/skills-generate.yml
@@ -0,0 +1,57 @@
+# 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.
+
+name: Generate Skills
+
+on:
+  pull_request:
+    paths:
+      - "toolbox_version.txt"
+
+jobs:
+  generate-skills:
+    # Only run for same-repo PRs (e.g. renovate's toolbox bump), where the
+    # built-in GITHUB_TOKEN can push back to the PR branch.
+    if: github.event.pull_request.head.repo.full_name == github.repository
+    runs-on: ubuntu-latest
+    permissions:
+      contents: write
+    steps:
+      - name: Check out PR branch
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6
+        with:
+          ref: ${{ github.head_ref }}
+
+      - name: Generate skills
+        run: |
+          VERSION="$(tr -d '\n' < toolbox_version.txt)"
+          echo "Detected toolbox version: $VERSION"
+          export VERSION
+          chmod +x ./.github/scripts/generate_skills.sh
+          ./.github/scripts/generate_skills.sh
+
+      - name: Commit and push regenerated skills
+        run: |
+          if [ -z "$(git status --porcelain)" ]; then
+            echo "No skill changes generated. Nothing to commit."
+            exit 0
+          fi
+
+          echo "Changes detected. Committing regenerated skills..."
+          git config user.name "release-please[bot]"
+          git config user.email "55107282+release-please[bot]@users.noreply.github.com"
+
+          git add .
+          git commit -m "chore: auto-generate skills for toolbox v$(tr -d '\n' < toolbox_version.txt)"
+          git push