diff --git a/installer/package.json b/installer/package.json
index 04cd9997..c764709a 100644
--- a/installer/package.json
+++ b/installer/package.json
@@ -1,6 +1,6 @@
 {
   "name": "syncable-cli-skills",
-  "version": "0.1.3",
+  "version": "0.1.5",
   "type": "module",
   "description": "Install Syncable CLI skills for AI coding agents (Claude Code, Cursor, Windsurf, Codex, Gemini CLI)",
   "license": "GPL-3.0",
diff --git a/installer/src/index.ts b/installer/src/index.ts
index f01e740c..ab78d98d 100644
--- a/installer/src/index.ts
+++ b/installer/src/index.ts
@@ -210,7 +210,8 @@ program
       if (syncCtlStatus.status === 'ok') {
         console.log(chalk.green(`  ✓ sync-ctl v${syncCtlStatus.version}`));
       } else if (syncCtlStatus.status === 'outdated') {
-        console.log(chalk.yellow(`  ⚠ sync-ctl v${syncCtlStatus.version} (outdated)`));
+        const latestInfo = syncCtlStatus.latestVersion ? ` → ${syncCtlStatus.latestVersion} available` : '';
+        console.log(chalk.yellow(`  ⚠ sync-ctl v${syncCtlStatus.version} (outdated${latestInfo})`));
       } else {
         console.log(chalk.red('  ✗ sync-ctl not found'));
       }
@@ -236,21 +237,30 @@ program
       if (syncCtlStatus.status === 'missing' || syncCtlStatus.status === 'outdated') {
         const cargoNow = await checkCargo();
         if (cargoNow.status === 'ok') {
-          const message = syncCtlStatus.status === 'outdated'
-            ? 'Update syncable-cli via cargo?'
-            : 'Install syncable-cli via cargo?';
-          const { installCli } = opts.yes
-            ? { installCli: true }
-            : await inquirer.prompt([{ type: 'confirm', name: 'installCli', message, default: true }]);
-
-          if (installCli) {
-            const spinner = ora('  Running: cargo install syncable-cli').start();
-            const force = syncCtlStatus.status === 'outdated';
-            const success = await installSyncCtl(force);
+          if (syncCtlStatus.status === 'outdated') {
+            // Always auto-upgrade to latest — no prompt needed
+            const latestLabel = syncCtlStatus.latestVersion ? ` to v${syncCtlStatus.latestVersion}` : '';
+            const spinner = ora(`  Upgrading sync-ctl${latestLabel}...`).start();
+            const success = await installSyncCtl(true); // force = true for upgrade
             if (success) {
-              spinner.succeed('  sync-ctl installed');
+              spinner.succeed(`  sync-ctl upgraded${latestLabel}`);
             } else {
-              spinner.fail('  Failed to install sync-ctl. Try: cargo install syncable-cli');
+              spinner.fail('  Failed to upgrade sync-ctl. Try: cargo install syncable-cli --force');
+            }
+          } else {
+            // Missing — ask to install
+            const { installCli } = opts.yes
+              ? { installCli: true }
+              : await inquirer.prompt([{ type: 'confirm', name: 'installCli', message: 'Install syncable-cli via cargo?', default: true }]);
+
+            if (installCli) {
+              const spinner = ora('  Running: cargo install syncable-cli').start();
+              const success = await installSyncCtl(false);
+              if (success) {
+                spinner.succeed('  sync-ctl installed');
+              } else {
+                spinner.fail('  Failed to install sync-ctl. Try: cargo install syncable-cli');
+              }
             }
           }
         }
@@ -441,7 +451,8 @@ program
     const projectOnlyFlag = opts.projectOnly ? ['--project-only'] : [];
     const verboseFlag = opts.verbose ? ['--verbose'] : [];
     await program.commands.find((c) => c.name() === 'uninstall')!.parseAsync(['node', 'x', ...agentsFlag, ...yesFlag]);
-    await program.commands.find((c) => c.name() === 'install')!.parseAsync(['node', 'x', '--skip-cli', ...agentsFlag, ...yesFlag, ...dryRunFlag, ...globalOnlyFlag, ...projectOnlyFlag, ...verboseFlag]);
+    // NOTE: Do NOT pass --skip-cli here — update must always check for and install the latest sync-ctl
+    await program.commands.find((c) => c.name() === 'install')!.parseAsync(['node', 'x', ...agentsFlag, ...yesFlag, ...dryRunFlag, ...globalOnlyFlag, ...projectOnlyFlag, ...verboseFlag]);
   });
 
 program
diff --git a/installer/src/prerequisites/check.ts b/installer/src/prerequisites/check.ts
index ad3761ab..93f6cfcd 100644
--- a/installer/src/prerequisites/check.ts
+++ b/installer/src/prerequisites/check.ts
@@ -2,10 +2,12 @@ import { execCommand, commandExists, parseVersion, compareVersions, cargoBinDir
 import { MIN_SYNC_CTL_VERSION } from '../constants.js';
 import fs from 'fs';
 import path from 'path';
+import https from 'https';
 
 export interface PrereqStatus {
   status: 'ok' | 'missing' | 'outdated';
   version?: string;
+  latestVersion?: string;
 }
 
 export function checkNodeVersion(): PrereqStatus {
@@ -31,6 +33,34 @@ export async function checkCargo(): Promise<PrereqStatus> {
   }
 }
 
+/**
+ * Fetch the latest syncable-cli version from crates.io.
+ * Returns null if the lookup fails (network error, timeout, etc.)
+ */
+export async function getLatestCratesVersion(): Promise<string | null> {
+  return new Promise((resolve) => {
+    const req = https.get(
+      'https://crates.io/api/v1/crates/syncable-cli',
+      { headers: { 'User-Agent': 'syncable-cli-skills-installer' }, timeout: 5_000 },
+      (res) => {
+        let data = '';
+        res.on('data', (chunk: Buffer) => { data += chunk; });
+        res.on('end', () => {
+          try {
+            const json = JSON.parse(data);
+            const version = json?.crate?.max_version || json?.versions?.[0]?.num;
+            resolve(version || null);
+          } catch {
+            resolve(null);
+          }
+        });
+      },
+    );
+    req.on('error', () => resolve(null));
+    req.on('timeout', () => { req.destroy(); resolve(null); });
+  });
+}
+
 export async function checkSyncCtl(): Promise<PrereqStatus> {
   try {
     const { stdout } = await execCommand('sync-ctl --version');
@@ -39,12 +69,24 @@ export async function checkSyncCtl(): Promise<PrereqStatus> {
       return { status: 'ok', version: stdout.trim() };
     }
 
+    const currentStr = `${version.major}.${version.minor}.${version.patch}`;
+
+    // First check: is it below the hard minimum?
     const minVersion = parseVersion(MIN_SYNC_CTL_VERSION);
     if (minVersion && compareVersions(version, minVersion) < 0) {
-      return { status: 'outdated', version: `${version.major}.${version.minor}.${version.patch}` };
+      return { status: 'outdated', version: currentStr };
+    }
+
+    // Second check: is there a newer version on crates.io?
+    const latestStr = await getLatestCratesVersion();
+    if (latestStr) {
+      const latest = parseVersion(latestStr);
+      if (latest && compareVersions(version, latest) < 0) {
+        return { status: 'outdated', version: currentStr, latestVersion: latestStr };
+      }
     }
 
-    return { status: 'ok', version: `${version.major}.${version.minor}.${version.patch}` };
+    return { status: 'ok', version: currentStr };
   } catch {
     return { status: 'missing' };
   }