diff --git a/.github/workflows/documentation-check.yaml b/.github/workflows/documentation-check.yaml
new file mode 100644
index 0000000000000..b95d29d4ab3a3
--- /dev/null
+++ b/.github/workflows/documentation-check.yaml
@@ -0,0 +1,310 @@
+name: AI Documentation Updates Automation
+
+on:
+  pull_request:
+    types:
+      - opened
+      - synchronize
+      - reopened
+  workflow_dispatch:
+    inputs:
+      pr_number:
+        description: "Pull Request number to process"
+        required: true
+        type: number
+
+jobs:
+  documentation-check:
+    name: Check Documentation Updates with Claude Code
+    runs-on: ubuntu-latest
+    timeout-minutes: 30
+    env:
+      CODER_URL: ${{ secrets.TRAIAGE_CODER_URL }}
+      CODER_SESSION_TOKEN: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
+    permissions:
+      contents: read
+      pull-requests: write
+      actions: write
+
+    steps:
+      - name: Determine Inputs
+        id: determine-inputs
+        if: always()
+        env:
+          GITHUB_ACTOR: ${{ github.actor }}
+          GITHUB_EVENT_NAME: ${{ github.event_name }}
+          GITHUB_EVENT_PR_NUMBER: ${{ github.event.pull_request.number }}
+          GITHUB_EVENT_USER_ID: ${{ github.event.sender.id }}
+          GITHUB_EVENT_USER_LOGIN: ${{ github.event.sender.login }}
+          INPUTS_PR_NUMBER: ${{ inputs.pr_number }}
+          GH_TOKEN: ${{ github.token }}
+        run: |
+          # For workflow_dispatch, use the actor who triggered it
+          # For pull_request events, use the PR author
+          if [[ "${GITHUB_EVENT_NAME}" == "workflow_dispatch" ]]; then
+            if ! GITHUB_USER_ID=$(gh api "users/${GITHUB_ACTOR}" --jq '.id'); then
+              echo "::error::Failed to get GitHub user ID for actor ${GITHUB_ACTOR}"
+              exit 1
+            fi
+            echo "Using workflow_dispatch actor: ${GITHUB_ACTOR} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_ACTOR}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using PR number: ${INPUTS_PR_NUMBER}"
+            echo "pr_number=${INPUTS_PR_NUMBER}" >> "${GITHUB_OUTPUT}"
+
+            exit 0
+          elif [[ "${GITHUB_EVENT_NAME}" == "pull_request" ]]; then
+            GITHUB_USER_ID=${GITHUB_EVENT_USER_ID}
+            echo "Using PR author: ${GITHUB_EVENT_USER_LOGIN} (ID: ${GITHUB_USER_ID})"
+            echo "github_user_id=${GITHUB_USER_ID}" >> "${GITHUB_OUTPUT}"
+            echo "github_username=${GITHUB_EVENT_USER_LOGIN}" >> "${GITHUB_OUTPUT}"
+
+            echo "Using PR number: ${GITHUB_EVENT_PR_NUMBER}"
+            echo "pr_number=${GITHUB_EVENT_PR_NUMBER}" >> "${GITHUB_OUTPUT}"
+
+            exit 0
+          else
+            echo "::error::Unsupported event type: ${GITHUB_EVENT_NAME}"
+            exit 1
+          fi
+
+      - name: Verify push access
+        env:
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          GH_TOKEN: ${{ github.token }}
+          GITHUB_USERNAME: ${{ steps.determine-inputs.outputs.github_username }}
+          GITHUB_USER_ID: ${{ steps.determine-inputs.outputs.github_user_id }}
+        run: |
+          # Query the actor's permission on this repo
+          can_push="$(gh api "/repos/${GITHUB_REPOSITORY}/collaborators/${GITHUB_USERNAME}/permission" --jq '.user.permissions.push')"
+          if [[ "${can_push}" != "true" ]]; then
+            echo "::error title=Access Denied::${GITHUB_USERNAME} does not have push access to ${GITHUB_REPOSITORY}"
+            exit 1
+          fi
+
+      - name: Post initial comment
+        env:
+          GH_TOKEN: ${{ github.token }}
+          PR_NUMBER: ${{ steps.determine-inputs.outputs.pr_number }}
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          RUN_ID: ${{ github.run_id }}
+        run: |
+          COMMENT_BODY=$(cat <<EOF
+          🤖 **Documentation Check Started**
+
+          Analyzing PR changes to determine if documentation updates are needed...
+
+          [View workflow run](https://github.com/${GITHUB_REPOSITORY}/actions/runs/${RUN_ID})
+          EOF
+          )
+          gh pr comment "${PR_NUMBER}" --body "${COMMENT_BODY}" --repo "${GITHUB_REPOSITORY}" --create-if-none --edit-last
+
+      - name: Download and install Coder binary
+        shell: bash
+        env:
+          CODER_URL: ${{ secrets.TRAIAGE_CODER_URL }}
+        run: |
+          if [ "${{ runner.arch }}" == "ARM64" ]; then
+            ARCH="arm64"
+          else
+            ARCH="amd64"
+          fi
+          mkdir -p "${HOME}/.local/bin"
+          curl -fsSL --compressed "$CODER_URL/bin/coder-linux-${ARCH}" -o "${HOME}/.local/bin/coder"
+          chmod +x "${HOME}/.local/bin/coder"
+          export PATH="$HOME/.local/bin:$PATH"
+          coder version
+          coder whoami
+          echo "$HOME/.local/bin" >> "${GITHUB_PATH}"
+
+      - name: Get Coder username from GitHub actor
+        id: get-coder-username
+        env:
+          CODER_SESSION_TOKEN: ${{ secrets.TRAIAGE_CODER_SESSION_TOKEN }}
+          GH_TOKEN: ${{ github.token }}
+          GITHUB_USER_ID: ${{ steps.determine-inputs.outputs.github_user_id }}
+        run: |
+          user_json=$(
+            coder users list --github-user-id="${GITHUB_USER_ID}" --output=json
+          )
+          coder_username=$(jq -r 'first | .username' <<< "$user_json")
+          [[ -z "${coder_username}" || "${coder_username}" == "null" ]] && echo "No Coder user with GitHub user ID ${GITHUB_USER_ID} found" && exit 1
+          echo "coder_username=${coder_username}" >> "${GITHUB_OUTPUT}"
+
+      - name: Checkout repository
+        uses: actions/checkout@v4
+        with:
+          persist-credentials: false
+          fetch-depth: 0
+
+      - name: Create Coder task for documentation analysis
+        id: create-task
+        env:
+          CODER_USERNAME: ${{ steps.get-coder-username.outputs.coder_username }}
+          GH_TOKEN: ${{ github.token }}
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          PR_NUMBER: ${{ steps.determine-inputs.outputs.pr_number }}
+          RUN_ID: ${{ github.run_id }}
+          TEMPLATE_NAME: "traiage"
+          TEMPLATE_PRESET: "Default"
+        run: |
+          # Fetch PR details using `gh` CLI
+          pr_json=$(gh pr view "${PR_NUMBER}" --repo "${GITHUB_REPOSITORY}" --json 'url')
+          pr_url=$(echo "${pr_json}" | jq -r '.url')
+
+          # Build comprehensive prompt
+          PROMPT=$(cat <<'EOF'
+          Analyze PR ${pr_url} for documentation updates.
+
+          ## Task Description
+          You are tasked with analyzing code changes in a pull request and determining what documentation updates are needed. Please:
+
+          1. Use the GitHub CLI or API to fetch the PR details, including:
+             - PR title and description
+             - List of files changed
+             - The actual code diff
+          2. Review the PR description and code changes to understand what was changed
+          3. Examine the existing documentation in the docs/ directory
+          4. Identify any of the following needs:
+             - Updates required to existing documentation
+             - Documentation that needs to be deprecated
+             - New documentation that should be added
+          5. Provide a clear, actionable list of documentation changes needed
+
+          ## PR to Analyze
+          ${pr_url}
+
+          ## IMPORTANT: Final Output Format
+          After completing your analysis, you MUST end your response with ONLY the following formatted output between the markers:
+
+          ---DOCUMENTATION-ANALYSIS-START---
+          [Your concise bulleted list of recommendations OR "No documentation changes needed"]
+          ---DOCUMENTATION-ANALYSIS-END---
+
+          The content between these markers should be:
+          - A simple bulleted list with links to docs that need updating
+          - OR a single sentence: "No documentation changes needed - [brief reason]"
+          - Maximum 10-15 lines
+          - Use markdown formatting
+          - Include file paths as links when referencing docs
+
+          Example format:
+          ---DOCUMENTATION-ANALYSIS-START---
+          ### Documentation Updates Needed
+          - **Update** [docs/admin/templates.md](docs/admin/templates.md) - Add new parameter documentation
+          - **Create** docs/guides/new-feature.md - Document the new feature workflow
+          - **Deprecate** docs/old-feature.md - Feature has been removed
+          ---DOCUMENTATION-ANALYSIS-END---
+
+          OR:
+
+          ---DOCUMENTATION-ANALYSIS-START---
+          No documentation changes needed - This PR only contains internal refactoring with no user-facing changes.
+          ---DOCUMENTATION-ANALYSIS-END---
+          EOF
+          )
+          # Expand variables in the prompt
+          PROMPT=$(eval "cat <<EOF
+          ${PROMPT}
+          EOF
+          ")
+          export PROMPT
+
+          export TASK_NAME="doccheck-pr-${PR_NUMBER}"
+          export CONTEXT_KEY="gh-pr-${PR_NUMBER}"
+          echo "Creating task: ${CODER_USERNAME}/${TASK_NAME}"
+
+          ./scripts/documentation-check.sh create
+
+          echo "TASK_NAME=${CODER_USERNAME}/${TASK_NAME}" >> "${GITHUB_OUTPUT}"
+          echo "TASK_NAME=${CODER_USERNAME}/${TASK_NAME}" >> "${GITHUB_ENV}"
+
+      - name: Update comment with task link
+        env:
+          GH_TOKEN: ${{ github.token }}
+          PR_NUMBER: ${{ steps.determine-inputs.outputs.pr_number }}
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          TASK_NAME: ${{ steps.create-task.outputs.TASK_NAME }}
+          RUN_ID: ${{ github.run_id }}
+        run: |
+          COMMENT_BODY=$(cat <<EOF
+          🤖 **Documentation Check Started**
+
+          Analyzing PR changes to determine if documentation updates are needed...
+
+          [View workflow run](https://github.com/${GITHUB_REPOSITORY}/actions/runs/${RUN_ID})
+
+          ---
+
+          🔄 **Analysis in progress...**
+
+          📋 Task: https://dev.coder.com/tasks/${TASK_NAME}
+          EOF
+          )
+
+          gh pr comment "${PR_NUMBER}" --body "${COMMENT_BODY}" --repo "${GITHUB_REPOSITORY}" --edit-last
+
+      - name: Wait for task completion and get results
+        id: get-results
+        env:
+          TASK_NAME: ${{ steps.create-task.outputs.TASK_NAME }}
+        run: |
+          START_TIME=$(date +%s)
+
+          echo "Waiting for task to complete..."
+          ./scripts/documentation-check.sh wait
+
+          echo "Getting task results..."
+          TASK_OUTPUT=$(./scripts/documentation-check.sh summary)
+
+          END_TIME=$(date +%s)
+          DURATION=$((END_TIME - START_TIME))
+
+          # Convert to minutes and seconds
+          MINUTES=$((DURATION / 60))
+          SECONDS=$((DURATION % 60))
+
+          if [ $MINUTES -gt 0 ]; then
+            DURATION_STR="${MINUTES}m ${SECONDS}s"
+          else
+            DURATION_STR="${SECONDS}s"
+          fi
+
+          # Save output to file for next step
+          echo "${TASK_OUTPUT}" > /tmp/task_output.txt
+          echo "${DURATION_STR}" > /tmp/task_duration.txt
+
+          echo "Task completed successfully in ${DURATION_STR}"
+
+      - name: Update PR comment with results
+        env:
+          GH_TOKEN: ${{ github.token }}
+          PR_NUMBER: ${{ steps.determine-inputs.outputs.pr_number }}
+          GITHUB_REPOSITORY: ${{ github.repository }}
+          TASK_NAME: ${{ steps.create-task.outputs.TASK_NAME }}
+          RUN_ID: ${{ github.run_id }}
+        run: |
+          TASK_OUTPUT=$(cat /tmp/task_output.txt)
+          DURATION=$(cat /tmp/task_duration.txt)
+
+          COMMENT_BODY=$(cat <<EOF
+          🤖 **Documentation Check Started**
+
+          Analyzing PR changes to determine if documentation updates are needed...
+
+          [View workflow run](https://github.com/${GITHUB_REPOSITORY}/actions/runs/${RUN_ID})
+
+          ---
+
+          ${TASK_OUTPUT}
+
+          ---
+          ⏱️ Execution time: **${DURATION}**
+          📋 Task: https://dev.coder.com/tasks/${TASK_NAME}
+          🔗 [View workflow run](https://github.com/${GITHUB_REPOSITORY}/actions/runs/${RUN_ID})
+          EOF
+          )
+
+          gh pr comment "${PR_NUMBER}" --body "${COMMENT_BODY}" --repo "${GITHUB_REPOSITORY}" --edit-last
+
diff --git a/scripts/documentation-check.sh b/scripts/documentation-check.sh
new file mode 100755
index 0000000000000..97ba248de815c
--- /dev/null
+++ b/scripts/documentation-check.sh
@@ -0,0 +1,147 @@
+#!/usr/bin/env bash
+
+SCRIPT_DIR=$(dirname "${BASH_SOURCE[0]}")
+# shellcheck source=scripts/lib.sh
+source "${SCRIPT_DIR}/lib.sh"
+
+CODER_BIN=${CODER_BIN:-"$(which coder)"}
+
+TEMPDIR=$(mktemp -d)
+trap 'rm -rf "${TEMPDIR}"' EXIT
+
+[[ -n ${VERBOSE:-} ]] && set -x
+set -euo pipefail
+
+usage() {
+	echo "Usage: $0 <options>"
+	echo "Commands:"
+	echo "  create      - Create a new documentation check task"
+	echo "  wait        - Wait for task to complete"
+	echo "  summary     - Get task output summary"
+	echo "  delete      - Delete the task"
+	exit 1
+}
+
+create() {
+	requiredenvs CODER_URL CODER_SESSION_TOKEN CODER_USERNAME TASK_NAME TEMPLATE_NAME TEMPLATE_PRESET PROMPT
+
+	# Check if a task already exists
+	set +e
+	task_json=$("${CODER_BIN}" \
+		--url "${CODER_URL}" \
+		--token "${CODER_SESSION_TOKEN}" \
+		exp tasks status "${CODER_USERNAME}/${TASK_NAME}" \
+		--output json 2>/dev/null)
+	set -e
+
+	if [[ "${TASK_NAME}" == $(jq -r '.name' <<<"${task_json}" 2>/dev/null) ]]; then
+		echo "Task \"${CODER_USERNAME}/${TASK_NAME}\" already exists. Sending prompt to existing task."
+		prompt
+		exit 0
+	fi
+
+	"${CODER_BIN}" \
+		--url "${CODER_URL}" \
+		--token "${CODER_SESSION_TOKEN}" \
+		exp tasks create \
+		--name "${TASK_NAME}" \
+		--template "${TEMPLATE_NAME}" \
+		--preset "${TEMPLATE_PRESET}" \
+		--org coder \
+		--owner "${CODER_USERNAME}" \
+		--stdin <<<"${PROMPT}"
+	exit 0
+}
+
+prompt() {
+	requiredenvs CODER_URL CODER_SESSION_TOKEN TASK_NAME PROMPT
+
+	${CODER_BIN} \
+		--url "${CODER_URL}" \
+		--token "${CODER_SESSION_TOKEN}" \
+		exp tasks status "${TASK_NAME}" \
+		--watch >/dev/null
+
+	${CODER_BIN} \
+		--url "${CODER_URL}" \
+		--token "${CODER_SESSION_TOKEN}" \
+		exp tasks send "${TASK_NAME}" \
+		--stdin \
+		<<<"${PROMPT}"
+}
+
+wait_for_completion() {
+	requiredenvs CODER_URL CODER_SESSION_TOKEN TASK_NAME
+
+	${CODER_BIN} \
+		--url "${CODER_URL}" \
+		--token "${CODER_SESSION_TOKEN}" \
+		exp tasks status "${TASK_NAME}" \
+		--watch >/dev/null
+}
+
+summary() {
+	requiredenvs CODER_URL CODER_SESSION_TOKEN TASK_NAME
+
+	last_msg_json=$(
+		${CODER_BIN} \
+			--url "${CODER_URL}" \
+			--token "${CODER_SESSION_TOKEN}" \
+			exp tasks logs "${TASK_NAME}" \
+			--output json
+	)
+
+	# Extract the last output message from the task
+	last_output_msg=$(jq -r 'last(.[] | select(.type=="output")) | .content' <<<"${last_msg_json}")
+
+	# Extract only the content between the documentation analysis markers
+	if echo "${last_output_msg}" | grep -q "---DOCUMENTATION-ANALYSIS-START---"; then
+		# Extract content between markers
+		summary=$(echo "${last_output_msg}" | sed -n '/---DOCUMENTATION-ANALYSIS-START---/,/---DOCUMENTATION-ANALYSIS-END---/p' | sed '1d;$d')
+		echo "${summary}"
+	else
+		# Fallback: if markers not found, return a message
+		echo "⚠️ Unable to extract documentation analysis. Please check the [task logs](https://dev.coder.com/tasks/${TASK_NAME})."
+	fi
+}
+
+delete() {
+	requiredenvs CODER_URL CODER_SESSION_TOKEN TASK_NAME
+
+	"${CODER_BIN}" \
+		--url "${CODER_URL}" \
+		--token "${CODER_SESSION_TOKEN}" \
+		delete \
+		"${TASK_NAME}" \
+		--yes
+	exit 0
+}
+
+main() {
+	dependencies coder
+
+	if [[ $# -eq 0 ]]; then
+		usage
+	fi
+
+	case "$1" in
+	create)
+		create
+		;;
+	wait)
+		wait_for_completion
+		;;
+	summary)
+		summary
+		;;
+	delete)
+		delete
+		;;
+	*)
+		echo "Unknown option: $1"
+		usage
+		;;
+	esac
+}
+
+main "$@"