diff --git a/.github/scripts/generate_skills.sh b/.github/scripts/generate_skills.sh
new file mode 100755
index 0000000..7cc9f30
--- /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 "$VERSION" ]; then
+  echo "Error: VERSION environment variable is not set."
+  exit 1
+fi
+
+# SKILL CONFIGURATION
+# Format: "skill-name" "prebuilt" "toolset" "description"
+# Looker ships two separate prebuilt configs (looker, looker-dev), each with its
+# own toolset, and the skill names do not follow a "<prefix>-<toolset>"
+# convention, so prebuilt + toolset + name are all configured explicitly.
+SKILLS=(
+  "looker"
+  "looker"
+  "looker_tools"
+  "These skills are designed for data discovery and business intelligence. "
+
+  "looker-dev"
+  "looker-dev"
+  "looker_dev_tools"
+  "These skills are built for LookML developers, data engineers, and administrators who manage the backbone of Looker."
+)
+
+echo "VALIDATING TOOLSETS BEFORE GENERATION"
+
+# Collect the unique prebuilt configs referenced by the SKILLS array.
+PREBUILTS=()
+set -- "${SKILLS[@]}"
+while [ $# -gt 0 ]; do
+  prebuilt="$2"
+  case " ${PREBUILTS[*]} " in
+    *" ${prebuilt} "*) ;;
+    *) PREBUILTS+=("$prebuilt") ;;
+  esac
+  shift 4
+done
+
+# Validate each prebuilt's upstream toolsets against the toolsets we generate
+# from that prebuilt. A new upstream toolset fails the job until a generator is
+# added to the SKILLS array.
+for prebuilt in "${PREBUILTS[@]}"; do
+  # Supported toolsets for this specific prebuilt.
+  SUPPORTED_TOOLSETS=()
+  set -- "${SKILLS[@]}"
+  while [ $# -gt 0 ]; do
+    if [ "$2" = "$prebuilt" ]; then
+      SUPPORTED_TOOLSETS+=("$3")
+    fi
+    shift 4
+  done
+
+  echo "Prebuilt '$prebuilt' supported toolsets: ${SUPPORTED_TOOLSETS[*]}"
+
+  # Fetch the upstream source of truth YAML for this prebuilt and version.
+  RAW_URL="https://raw.githubusercontent.com/googleapis/mcp-toolbox/v${VERSION}/internal/prebuiltconfigs/tools/${prebuilt}.yaml"
+  echo "Fetching upstream config from: $RAW_URL"
+  UPSTREAM_YAML=$(curl -sL --fail "$RAW_URL" || { echo "Error: Could not fetch upstream YAML for $prebuilt v$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}')
+
+  for upstream_tool in $UPSTREAM_TOOLSETS; do
+    if [ -z "$upstream_tool" ] || [ "$upstream_tool" == "-" ]; then continue; fi
+
+    if [[ ! " ${SUPPORTED_TOOLSETS[*]} " =~ " ${upstream_tool} " ]]; then
+      echo "ERROR: Upstream config '$prebuilt' contains a new toolset: '$upstream_tool'"
+      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 a generator"
+      echo "for the missing toolset above, then commit your changes to unblock this PR."
+      exit 1
+    fi
+  done
+done
+
+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 SKILL_NAME="$1"
+  local PREBUILT="$2"
+  local TOOLSET="$3"
+  local SKILL_DESC="$4"
+
+  echo "Generating skill: $SKILL_NAME (prebuilt: $PREBUILT)..."
+
+  npx "@toolbox-sdk/server@${VERSION}" --prebuilt "$PREBUILT" skills-generate \
+    --name "$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" "$3" "$4"
+  shift 4
+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