diff --git a/.claude-plugin/check_update.sh b/.claude-plugin/check_update.sh
new file mode 100755
index 00000000..e7a744c1
--- /dev/null
+++ b/.claude-plugin/check_update.sh
@@ -0,0 +1,78 @@
+#!/bin/bash
+# Version update check for Databricks AI Dev Kit.
+# Stdout from this script is injected as context Claude can see at session start.
+# Silent on success (up to date) or failure (network error, missing files).
+
+# Find the installed version. Check multiple locations:
+# 1. Plugin mode: VERSION at plugin root
+# 2. Project-scoped install: .ai-dev-kit/version in project dir
+# 3. Global install: ~/.ai-dev-kit/version
+# 4. Fallback: script-relative
+VERSION_FILE=""
+for candidate in \
+    "${CLAUDE_PLUGIN_ROOT:+$CLAUDE_PLUGIN_ROOT/VERSION}" \
+    "${CLAUDE_PROJECT_DIR:+$CLAUDE_PROJECT_DIR/.ai-dev-kit/version}" \
+    "$HOME/.ai-dev-kit/version" \
+    "$(cd "$(dirname "${BASH_SOURCE[0]}")/.." && pwd)/VERSION"; do
+    [ -n "$candidate" ] && [ -f "$candidate" ] && VERSION_FILE="$candidate" && break
+done
+CACHE_FILE="$HOME/.ai-dev-kit/.update-check"
+REMOTE_URL="https://raw.githubusercontent.com/databricks-solutions/ai-dev-kit/main/VERSION"
+CACHE_TTL=86400  # 24 hours
+
+[ ! -f "$VERSION_FILE" ] && exit 0
+local_ver=$(cat "$VERSION_FILE" 2>/dev/null)
+[ -z "$local_ver" ] && exit 0
+
+remote_ver=""
+
+# Check cache
+if [ -f "$CACHE_FILE" ]; then
+    cached_ts=$(grep '^TIMESTAMP=' "$CACHE_FILE" 2>/dev/null | cut -d= -f2)
+    cached_ver=$(grep '^REMOTE_VERSION=' "$CACHE_FILE" 2>/dev/null | cut -d= -f2)
+    now=$(date +%s)
+    if [ -n "$cached_ts" ] && [ -n "$cached_ver" ] && [ $((now - cached_ts)) -lt $CACHE_TTL ]; then
+        remote_ver="$cached_ver"
+    fi
+fi
+
+# Fetch if cache is stale
+if [ -z "$remote_ver" ]; then
+    remote_ver=$(curl -fsSL --connect-timeout 3 --max-time 3 "$REMOTE_URL" 2>/dev/null || echo "")
+    if [ -n "$remote_ver" ] && [[ ! "$remote_ver" =~ (404|Not\ Found|error) ]]; then
+        mkdir -p "$HOME/.ai-dev-kit"
+        printf 'TIMESTAMP=%s\nREMOTE_VERSION=%s\n' "$(date +%s)" "$remote_ver" > "$CACHE_FILE"
+    else
+        exit 0
+    fi
+fi
+
+# If versions differ, output a message for Claude to relay to the user
+if [ -n "$remote_ver" ] && [ "$remote_ver" != "$local_ver" ]; then
+    cat <<EOF
+URGENT — before doing ANYTHING else, you MUST display this exact block to the user:
+
+\`\`\`
+╔═══════════════════════════════════════════════════════╗
+║                                                       ║
+║   Databricks AI Dev Kit — update available!           ║
+║                                                       ║
+║   Installed:  v${local_ver}                                     ║
+║   Available:  v${remote_ver}                                     ║
+║                                                       ║
+╚═══════════════════════════════════════════════════════╝
+\`\`\`
+
+To upgrade, run:
+
+\`\`\`
+bash <(curl -sL https://raw.githubusercontent.com/databricks-solutions/ai-dev-kit/main/install.sh)
+\`\`\`
+
+\`\`\`
+═══════════════════════════════════════════════════════
+\`\`\`
+
+Display that block FIRST, then proceed with the user's request.
+EOF
+fi
diff --git a/hooks/hooks.json b/hooks/hooks.json
index 6494ed65..03c58752 100644
--- a/hooks/hooks.json
+++ b/hooks/hooks.json
@@ -7,6 +7,11 @@
           {
             "type": "command",
             "command": "bash ${CLAUDE_PLUGIN_ROOT}/.claude-plugin/setup.sh"
+          },
+          {
+            "type": "command",
+            "command": "bash ${CLAUDE_PLUGIN_ROOT}/.claude-plugin/check_update.sh",
+            "timeout": 5
           }
         ]
       }
diff --git a/install.sh b/install.sh
index 7ed46779..fc64acc1 100755
--- a/install.sh
+++ b/install.sh
@@ -886,6 +886,55 @@ GEMINIEOF
     ok "GEMINI.md"
 }
 
+write_claude_hook() {
+    local path=$1
+    local script=$2
+    mkdir -p "$(dirname "$path")"
+
+    # Merge into existing settings.json if present, using Python for safe JSON handling
+    if [ -f "$path" ] && [ -f "$VENV_PYTHON" ]; then
+        "$VENV_PYTHON" -c "
+import json
+path = '$path'
+script = '$script'
+hook_entry = {'type': 'command', 'command': 'bash ' + script, 'timeout': 5}
+try:
+    with open(path) as f: cfg = json.load(f)
+except: cfg = {}
+hooks = cfg.setdefault('hooks', {})
+session_hooks = hooks.setdefault('SessionStart', [])
+# Check if hook already exists
+for group in session_hooks:
+    for h in group.get('hooks', []):
+        if 'check_update.sh' in h.get('command', ''):
+            exit(0)  # Already configured
+# Append new hook group
+session_hooks.append({'hooks': [hook_entry]})
+with open(path, 'w') as f: json.dump(cfg, f, indent=2); f.write('\n')
+" 2>/dev/null && return
+    fi
+
+    # Fallback: write new file (only if no existing file)
+    [ -f "$path" ] && return  # Don't overwrite existing settings without Python
+    cat > "$path" << EOF
+{
+  "hooks": {
+    "SessionStart": [
+      {
+        "hooks": [
+          {
+            "type": "command",
+            "command": "bash $script",
+            "timeout": 5
+          }
+        ]
+      }
+    ]
+  }
+}
+EOF
+}
+
 write_mcp_configs() {
     step "Configuring MCP"
     
@@ -895,6 +944,14 @@ write_mcp_configs() {
             claude)
                 [ "$SCOPE" = "global" ] && write_mcp_json "$HOME/.claude/mcp.json" || write_mcp_json "$base_dir/.mcp.json"
                 ok "Claude MCP config"
+                # Add version check hook to Claude settings
+                local check_script="$REPO_DIR/.claude-plugin/check_update.sh"
+                if [ "$SCOPE" = "global" ]; then
+                    write_claude_hook "$HOME/.claude/settings.json" "$check_script"
+                else
+                    write_claude_hook "$base_dir/.claude/settings.json" "$check_script"
+                fi
+                ok "Claude update check hook"
                 ;;
             cursor)
                 if [ "$SCOPE" = "global" ]; then