fix(plugins): retry claude plugin install|update without -y on an old CLI

An older Claude Code has no -y on `plugin install|update` and exits with
"error: unknown option '-y'", so the dashboard's Update now chain failed at
its plugin_update step (and so did Update all, the plugin buttons and the
superpowers auto-install). Those versions also predate the confirmation
prompt -y answers, so every wrapper now retries the same argv without it
when, and only when, the CLI rejects the flag. /agenthub-update, which the
failure message points users to, falls back the same way.

plugins/agenthub/commands/agenthub-update.md

@@ -17,7 +17,9 @@ if [ -z "$MARKETPLACE" ]; then
   echo "agenthub is not installed as a plugin (checkout install?) - nothing to update this way."
 else
   claude plugin marketplace update "$MARKETPLACE"
-  claude plugin update "agenthub@$MARKETPLACE" -y
+  # An older Claude Code has no `-y` (and no prompt for it to answer).
+  claude plugin update "agenthub@$MARKETPLACE" -y 2>/dev/null ||
+    claude plugin update "agenthub@$MARKETPLACE"
 fi
 ```
 

scripts/cc-update-all-helper.js

@@ -83,6 +83,21 @@ function resolveClaude() {
 }
 
 function run(cmd, args, timeout) {
+  try {
+    return runOnce(cmd, args, timeout);
+  } catch (err) {
+    // An older Claude Code rejects `-y` ("unknown option") and never prompts,
+    // so the same command without the flag is the right retry.
+    if (!args.includes("-y") || !/unknown option '-y'/.test(String(err.stderr || ""))) throw err;
+    return runOnce(
+      cmd,
+      args.filter((a) => a !== "-y"),
+      timeout
+    );
+  }
+}
+
+function runOnce(cmd, args, timeout) {
   log(`$ ${cmd} ${args.join(" ")}`);
   const out = execFileSync(cmd, args, {
     encoding: "utf8",

scripts/plugin-update-helper.js

@@ -102,6 +102,21 @@ function findNewRoot(exclude) {
 }
 
 function run(cmd, args, timeout) {
+  try {
+    return runOnce(cmd, args, timeout);
+  } catch (err) {
+    // An older Claude Code rejects `-y` ("unknown option") and never prompts,
+    // so the same command without the flag is the right retry.
+    if (!args.includes("-y") || !/unknown option '-y'/.test(String(err.stderr || ""))) throw err;
+    return runOnce(
+      cmd,
+      args.filter((a) => a !== "-y"),
+      timeout
+    );
+  }
+}
+
+function runOnce(cmd, args, timeout) {
   log(`$ ${cmd} ${args.join(" ")}`);
   const out = execFileSync(cmd, args, {
     encoding: "utf8",

server/__tests__/cc-plugin-cli.test.js

@@ -116,6 +116,22 @@ describe("cc-plugin-cli argv construction", () => {
     }
   });
 
+  it("retries without -y on a Claude Code too old to know the flag", async () => {
+    // Older CLIs answer `error: unknown option '-y'` and exit 1; they also
+    // never prompt, so the same command without the flag is the right retry.
+    const restore = stubClaude(
+      'for a in "$@"; do [ "$a" = "-y" ] && { echo "error: unknown option \'-y\'" >&2; exit 1; }; done\n' +
+        'for a in "$@"; do echo "$a"; done'
+    );
+    try {
+      const r = await cli.pluginUpdate({ spec: "demo@m" });
+      assert.equal(r.ok, true);
+      assert.deepEqual(argvOf(r), ["plugin", "update", "demo@m"]);
+    } finally {
+      restore();
+    }
+  });
+
   it("passes -y on install so a non-TTY run never waits for a prompt", async () => {
     const restore = stubClaude();
     try {

server/lib/cc-plugin-cli.js

@@ -130,7 +130,23 @@ function serialize(fn) {
  * @param {{timeoutMs?:number}} [opts]
  * @returns {Promise<{ok:boolean, code:number|null, stdout:string, stderr:string, args:string[]}>}
  */
-function runClaude(args, opts = {}) {
+// A Claude Code older than `plugin install|update -y` rejects the flag outright.
+// It also predates the confirmation prompt the flag answers, so the same
+// command without it is the correct retry, not a weaker one.
+const NO_YES_FLAG = /unknown option '-y'/;
+
+async function runClaude(args, opts = {}) {
+  const result = await runClaudeOnce(args, opts);
+  if (!result.ok && args.includes("-y") && NO_YES_FLAG.test(result.stderr)) {
+    return runClaudeOnce(
+      args.filter((a) => a !== "-y"),
+      opts
+    );
+  }
+  return result;
+}
+
+function runClaudeOnce(args, opts = {}) {
   const timeout = opts.timeoutMs || DEFAULT_TIMEOUT_MS;
   return new Promise((resolve, reject) => {
     // Only pin CLAUDE_CONFIG_DIR when the operator explicitly set CLAUDE_HOME

server/lib/skill-plugins.js

@@ -128,6 +128,18 @@ function missingSkillPlugins() {
  * @returns {{ok: boolean, output: string}}
  */
 function runClaudePlugin(args, timeoutMs) {
+  const result = runClaudePluginOnce(args, timeoutMs);
+  // An older Claude Code rejects `-y` and never prompts; retry without it.
+  if (!result.ok && args.includes("-y") && /unknown option '-y'/.test(result.output)) {
+    return runClaudePluginOnce(
+      args.filter((a) => a !== "-y"),
+      timeoutMs
+    );
+  }
+  return result;
+}
+
+function runClaudePluginOnce(args, timeoutMs) {
   const env = { ...process.env };
   if (process.env.CLAUDE_HOME) env.CLAUDE_CONFIG_DIR = getClaudeHome();
   const result = spawnSync("claude", args, {