diff --git a/plugin/scripts/smart-install.js b/plugin/scripts/smart-install.js
index f1f3b7ff..af44017b 100644
--- a/plugin/scripts/smart-install.js
+++ b/plugin/scripts/smart-install.js
@@ -65,6 +65,36 @@ function getBunPath() {
   return null;
 }
 
+/**
+ * Minimum required bun version
+ * v1.1.14+ required for .changes property and multi-statement SQL support
+ */
+const MIN_BUN_VERSION = '1.1.14';
+
+/**
+ * Compare semver versions
+ */
+function compareVersions(v1, v2) {
+  const parts1 = v1.split('.').map(Number);
+  const parts2 = v2.split('.').map(Number);
+  for (let i = 0; i < 3; i++) {
+    const p1 = parts1[i] || 0;
+    const p2 = parts2[i] || 0;
+    if (p1 > p2) return 1;
+    if (p1 < p2) return -1;
+  }
+  return 0;
+}
+
+/**
+ * Check if bun version meets minimum requirements
+ */
+function isBunVersionSufficient() {
+  const version = getBunVersion();
+  if (!version) return false;
+  return compareVersions(version, MIN_BUN_VERSION) >= 0;
+}
+
 /**
  * Get Bun version if installed
  */
@@ -377,7 +407,7 @@ function installDeps() {
 
 // Main execution
 try {
-  // Step 1: Ensure Bun is installed (REQUIRED)
+  // Step 1: Ensure Bun is installed and meets minimum version (REQUIRED)
   if (!isBunInstalled()) {
     installBun();
 
@@ -389,6 +419,25 @@ try {
     }
   }
 
+  // Step 1.5: Ensure Bun version is sufficient
+  if (!isBunVersionSufficient()) {
+    const currentVersion = getBunVersion();
+    console.error(`⚠️  Bun ${currentVersion} is outdated. Minimum required: ${MIN_BUN_VERSION}`);
+    console.error('   Upgrading bun...');
+    try {
+      execSync('bun upgrade', { stdio: 'inherit', shell: IS_WINDOWS });
+      if (!isBunVersionSufficient()) {
+        console.error(`❌ Bun upgrade failed. Please manually upgrade: bun upgrade`);
+        process.exit(1);
+      }
+      console.error(`✅ Bun upgraded to ${getBunVersion()}`);
+    } catch (error) {
+      console.error(`❌ Failed to upgrade bun: ${error.message}`);
+      console.error('   Please manually upgrade: bun upgrade');
+      process.exit(1);
+    }
+  }
+
   // Step 2: Ensure uv is installed (REQUIRED for vector search)
   if (!isUvInstalled()) {
     installUv();