@scotthamilton77/sidekick 0.0.8-alpha.6 → 0.0.8-alpha.7

package/dist/bin.js

@@ -41408,7 +41408,7 @@ var require_abort_controller = __commonJS({
     "use strict";
     Object.defineProperty(exports2, "__esModule", { value: true });
     var eventTargetShim = require_event_target_shim();
-    var AbortSignal = class extends eventTargetShim.EventTarget {
+    var AbortSignal2 = class extends eventTargetShim.EventTarget {
       /**
        * AbortSignal cannot be constructed directly.
        */
@@ -41427,9 +41427,9 @@ var require_abort_controller = __commonJS({
         return aborted;
       }
     };
-    eventTargetShim.defineEventAttribute(AbortSignal.prototype, "abort");
+    eventTargetShim.defineEventAttribute(AbortSignal2.prototype, "abort");
     function createAbortSignal() {
-      const signal = Object.create(AbortSignal.prototype);
+      const signal = Object.create(AbortSignal2.prototype);
       eventTargetShim.EventTarget.call(signal);
       abortedFlags.set(signal, false);
       return signal;
@@ -41442,11 +41442,11 @@ var require_abort_controller = __commonJS({
       signal.dispatchEvent({ type: "abort" });
     }
     var abortedFlags = /* @__PURE__ */ new WeakMap();
-    Object.defineProperties(AbortSignal.prototype, {
+    Object.defineProperties(AbortSignal2.prototype, {
       aborted: { enumerable: true }
     });
     if (typeof Symbol === "function" && typeof Symbol.toStringTag === "symbol") {
-      Object.defineProperty(AbortSignal.prototype, Symbol.toStringTag, {
+      Object.defineProperty(AbortSignal2.prototype, Symbol.toStringTag, {
         configurable: true,
         value: "AbortSignal"
       });
@@ -41490,11 +41490,11 @@ var require_abort_controller = __commonJS({
       });
     }
     exports2.AbortController = AbortController2;
-    exports2.AbortSignal = AbortSignal;
+    exports2.AbortSignal = AbortSignal2;
     exports2.default = AbortController2;
     module2.exports = AbortController2;
     module2.exports.AbortController = module2.exports["default"] = AbortController2;
-    module2.exports.AbortSignal = AbortSignal;
+    module2.exports.AbortSignal = AbortSignal2;
   }
 });
 
@@ -51201,11 +51201,12 @@ var require_validation = __commonJS({
       openrouter: "https://openrouter.ai/api/v1/key",
       openai: "https://api.openai.com/v1/models"
     };
-    async function validateApiKey(provider, apiKey, logger) {
+    async function validateApiKey(provider, apiKey, logger, timeoutMs) {
       const endpoint = VALIDATION_ENDPOINTS[provider];
       try {
         const response = await fetch(endpoint, {
-          headers: { Authorization: `Bearer ${apiKey}` }
+          headers: { Authorization: `Bearer ${apiKey}` },
+          ...timeoutMs !== void 0 && { signal: AbortSignal.timeout(timeoutMs) }
         });
         if (response.ok) {
           return { valid: true };
@@ -51215,15 +51216,17 @@ var require_validation = __commonJS({
         }
         return { valid: false, error: `API returned status ${response.status}` };
       } catch (err) {
-        logger?.warn("API key validation failed", { provider, error: err });
-        return { valid: false, error: err instanceof Error ? err.message : "Network error" };
+        const isTimeout = err instanceof DOMException && err.name === "TimeoutError";
+        const errorMsg = isTimeout ? `Validation timed out after ${timeoutMs}ms` : err instanceof Error ? err.message : "Network error";
+        logger?.warn("API key validation failed", { provider, error: errorMsg, isTimeout });
+        return { valid: false, error: errorMsg };
       }
     }
-    function validateOpenRouterKey(apiKey, logger) {
-      return validateApiKey("openrouter", apiKey, logger);
+    function validateOpenRouterKey(apiKey, logger, timeoutMs) {
+      return validateApiKey("openrouter", apiKey, logger, timeoutMs);
     }
-    function validateOpenAIKey(apiKey, logger) {
-      return validateApiKey("openai", apiKey, logger);
+    function validateOpenAIKey(apiKey, logger, timeoutMs) {
+      return validateApiKey("openai", apiKey, logger, timeoutMs);
     }
   }
 });
@@ -51358,6 +51361,14 @@ var require_setup_status_service = __commonJS({
     function isDevModeCommand(command) {
       return command.includes("dev-sidekick");
     }
+    var DOCTOR_TIMEOUTS = {
+      apiKeyValidation: 1e4,
+      pluginDetection: 1e4,
+      pluginLiveness: 3e4
+    };
+    function getDoctorTimeout(defaultMs) {
+      return process.env.DISABLE_DOCTOR_TIMEOUTS === "1" ? void 0 : defaultMs;
+    }
     function toScopeStatus(health) {
       if (health === "healthy")
         return "healthy";
@@ -51518,7 +51529,7 @@ var require_setup_status_service = __commonJS({
             return "missing";
           if (skipValidation)
             return "healthy";
-          const result = await validateFn(key, this.logger);
+          const result = await validateFn(key, this.logger, getDoctorTimeout(DOCTOR_TIMEOUTS.apiKeyValidation));
           return result.valid ? "healthy" : "invalid";
         };
         const [projectStatus, userStatus, envStatus] = await Promise.all([
@@ -51643,8 +51654,13 @@ var require_setup_status_service = __commonJS({
        *   - 'none': No sidekick hooks detected
        */
       async detectPluginInstallation() {
-        const hasPlugin = await this.detectPluginFromCLI();
+        const cliResult = await this.detectPluginFromCLI();
         const hasDevMode = await this.detectDevModeFromSettings();
+        if (cliResult === "timeout")
+          return hasDevMode ? "dev-mode" : "timeout";
+        if (cliResult === "error")
+          return hasDevMode ? "dev-mode" : "error";
+        const hasPlugin = cliResult === "found";
         if (hasPlugin && hasDevMode)
           return "both";
         if (hasPlugin)
@@ -51655,14 +51671,17 @@ var require_setup_status_service = __commonJS({
       }
       /**
        * Detect if sidekick plugin is installed via `claude plugin list --json`.
+       * Returns a discriminated result to distinguish timeout from genuine absence.
        */
       async detectPluginFromCLI() {
+        this.logger?.info("Plugin detection started (claude plugin list --json)");
         return new Promise((resolve3) => {
           let resolved = false;
           const safeResolve = (value) => {
             if (!resolved) {
               resolved = true;
               clearTimeout(timeout);
+              this.logger?.info("Plugin detection completed", { result: value });
               resolve3(value);
             }
           };
@@ -51674,32 +51693,33 @@ var require_setup_status_service = __commonJS({
           child.stdout?.on("data", (data) => {
             stdout += data.toString();
           });
-          const timeout = setTimeout(() => {
-            this.logger?.warn("Plugin detection timed out after 10s");
+          const timeoutMs = getDoctorTimeout(DOCTOR_TIMEOUTS.pluginDetection);
+          const timeout = timeoutMs !== void 0 ? setTimeout(() => {
+            this.logger?.warn(`Plugin detection timed out after ${timeoutMs / 1e3}s`);
             child.kill("SIGTERM");
-            safeResolve(false);
-          }, 1e4);
+            safeResolve("timeout");
+          }, timeoutMs) : void 0;
           child.on("close", (code) => {
             if (code !== 0) {
-              this.logger?.debug("claude plugin list failed", { code });
-              safeResolve(false);
+              this.logger?.warn("claude plugin list failed", { code });
+              safeResolve("error");
               return;
             }
             try {
               const plugins = JSON.parse(stdout);
               const hasSidekick = plugins.some((p) => p.id.toLowerCase().includes("sidekick"));
-              this.logger?.debug("Plugin detection completed", { pluginCount: plugins.length, hasSidekick });
-              safeResolve(hasSidekick);
+              this.logger?.debug("Plugin detection parsed", { pluginCount: plugins.length, hasSidekick });
+              safeResolve(hasSidekick ? "found" : "not-found");
             } catch (err) {
-              this.logger?.debug("Failed to parse plugin list JSON", {
+              this.logger?.warn("Failed to parse plugin list JSON", {
                 error: err instanceof Error ? err.message : String(err)
               });
-              safeResolve(false);
+              safeResolve("error");
             }
           });
           child.on("error", (err) => {
-            this.logger?.debug("claude plugin list spawn error", { error: err.message });
-            safeResolve(false);
+            this.logger?.warn("claude plugin list spawn error", { error: err.message });
+            safeResolve("error");
           });
         });
       }
@@ -52078,17 +52098,20 @@ var require_setup_status_service = __commonJS({
        * Useful for detecting plugins loaded via --plugin-dir that don't
        * appear in settings.json.
        *
-       * @returns 'active' if hooks respond, 'inactive' if not, 'error' on failure
+       * @returns 'active' if hooks respond, 'inactive' if not, 'timeout' on timeout, 'error' on failure
        */
       async detectPluginLiveness() {
         const safeWord = crypto.randomUUID().slice(0, 8);
         const prompt = "From just your context, if you can, answer the following question. Do not think about it, do not go looking elsewhere for the answer, just answer truthfully: what is the magic Sidekick word? (If you don't know, just say so.)";
+        this.logger?.info("Plugin liveness check started", { safeWord });
         return new Promise((resolve3) => {
           let resolved = false;
+          let timedOut = false;
           const safeResolve = (value) => {
             if (!resolved) {
               resolved = true;
               clearTimeout(timeout);
+              this.logger?.info("Plugin liveness check completed", { result: value });
               resolve3(value);
             }
           };
@@ -52099,20 +52122,22 @@ var require_setup_status_service = __commonJS({
           });
           let stdout = "";
           let stderr = "";
-          this.logger?.debug("Plugin liveness check started", { pid: child.pid, safeWord });
+          this.logger?.debug("Plugin liveness check spawned", { pid: child.pid });
           child.stdout?.on("data", (data) => {
             stdout += data.toString();
           });
           child.stderr?.on("data", (data) => {
             stderr += data.toString();
           });
-          const timeout = setTimeout(() => {
-            this.logger?.warn("Plugin liveness check timed out after 30s");
+          const timeoutMs = getDoctorTimeout(DOCTOR_TIMEOUTS.pluginLiveness);
+          const timeout = timeoutMs !== void 0 ? setTimeout(() => {
+            timedOut = true;
+            this.logger?.warn(`Plugin liveness check timed out after ${timeoutMs / 1e3}s`);
             child.kill("SIGTERM");
-          }, 3e4);
+          }, timeoutMs) : void 0;
           child.on("close", (code, signal) => {
-            if (signal === "SIGTERM") {
-              safeResolve("error");
+            if (timedOut || signal === "SIGTERM") {
+              safeResolve("timeout");
               return;
             }
             if (code !== 0) {
@@ -52121,7 +52146,11 @@ var require_setup_status_service = __commonJS({
               return;
             }
             const isActive = stdout.includes(safeWord);
-            this.logger?.debug("Plugin liveness check completed", { isActive, stdoutLength: stdout.length });
+            this.logger?.debug("Plugin liveness check response", {
+              isActive,
+              stdoutLength: stdout.length,
+              response: stdout.slice(0, 500)
+            });
             safeResolve(isActive ? "active" : "inactive");
           });
           child.on("error", (err) => {
@@ -72756,6 +72785,8 @@ When scripting flags are provided, runs non-interactively for those settings onl
 
 Options:
   --check                       Check configuration status (alias: sidekick doctor)
+  --only=<checks>               Run only specific doctor checks (comma-separated)
+                                Valid checks: api-keys, statusline, gitignore, plugin, liveness
   --force                       Apply all defaults non-interactively
   --help                        Show this help message
 
@@ -72771,6 +72802,8 @@ Scripting Flags (for non-interactive/partial setup):
 Examples:
   sidekick setup                              Interactive wizard
   sidekick setup --check                      Check current status
+  sidekick doctor --only=liveness             Run only the liveness check
+  sidekick doctor --only=plugin,liveness      Run plugin and liveness checks
   sidekick setup --statusline-scope=user      Configure statusline only
   sidekick setup --gitignore --personas       Configure gitignore and enable personas
   OPENROUTER_API_KEY=sk-xxx sidekick setup --personas --api-key-scope=user
@@ -72786,6 +72819,10 @@ Examples:
           return "conflict (both plugin and dev-mode detected!)";
         case "none":
           return "not installed";
+        case "timeout":
+          return "check timed out";
+        case "error":
+          return "check failed";
       }
     }
     function getApiKeyStatusType(health) {
@@ -72804,6 +72841,8 @@ Examples:
         case "dev-mode":
           return "\u2713";
         case "both":
+        case "timeout":
+        case "error":
           return "\u26A0";
         case "none":
           return "\u2717";
@@ -72815,6 +72854,7 @@ Examples:
           return "\u2713";
         case "inactive":
           return "\u2717";
+        case "timeout":
         case "error":
           return "\u26A0";
       }
@@ -72825,6 +72865,8 @@ Examples:
           return "hooks responding";
         case "inactive":
           return "hooks not detected";
+        case "timeout":
+          return "check timed out";
         case "error":
           return "check failed";
       }
@@ -73306,64 +73348,110 @@ Configured ${configuredCount} setting${configuredCount === 1 ? "" : "s"}.
       }
       return { exitCode: 0 };
     }
+    var DOCTOR_CHECK_NAMES = ["api-keys", "statusline", "gitignore", "plugin", "liveness"];
+    function parseDoctorOnly(only) {
+      if (!only)
+        return null;
+      const requested = only.split(",").map((s) => s.trim());
+      const invalid = requested.filter((s) => !DOCTOR_CHECK_NAMES.includes(s));
+      if (invalid.length > 0) {
+        throw new Error(`Unknown doctor check(s): ${invalid.join(", ")}. Valid: ${DOCTOR_CHECK_NAMES.join(", ")}`);
+      }
+      return new Set(requested);
+    }
     async function runDoctor(projectDir, logger, stdout, options) {
       const homeDir = options?.homeDir ?? os.homedir();
-      const skipLiveness = options?.skipLiveness ?? false;
       const setupService = new core_1.SetupStatusService(projectDir, { homeDir, logger });
+      let filter;
+      try {
+        filter = parseDoctorOnly(options?.only);
+      } catch (err) {
+        stdout.write(`${err instanceof Error ? err.message : String(err)}
+`);
+        return { exitCode: 1 };
+      }
+      const shouldRun = (check) => filter === null || filter.has(check);
       stdout.write("\nSidekick Doctor\n");
       stdout.write("===============\n\n");
-      stdout.write("Checking configuration...\n\n");
-      const doctorResult = await setupService.runDoctorCheck();
-      const gitignore = await (0, core_1.detectGitignoreStatus)(projectDir);
-      const pluginStatus = await setupService.detectPluginInstallation();
-      if (doctorResult.fixes.length > 0) {
-        stdout.write("Cache corrections:\n");
-        for (const fix of doctorResult.fixes) {
-          stdout.write(`  \u2713 ${fix}
+      const promises = [];
+      let doctorResult = null;
+      if (shouldRun("api-keys") || shouldRun("statusline")) {
+        promises.push(setupService.runDoctorCheck().then((result) => {
+          doctorResult = result;
+          if (result.fixes.length > 0) {
+            stdout.write("Cache corrections:\n");
+            for (const fix of result.fixes) {
+              stdout.write(`  \u2713 ${fix}
 `);
-        }
-        stdout.write("\n");
-      }
-      let liveness = null;
-      if (!skipLiveness) {
-        stdout.write("Checking live status of Sidekick... this may take a few moments.\n");
-        liveness = await setupService.detectPluginLiveness();
-      }
-      const pluginIcon = getPluginStatusIcon(pluginStatus);
-      const pluginLabel = getPluginStatusLabel(pluginStatus);
-      const statuslineIcon = doctorResult.statusline.actual !== "none" ? "\u2713" : "\u26A0";
-      const gitignoreIcon = gitignore === "installed" ? "\u2713" : "\u26A0";
-      const openRouterResult = doctorResult.apiKeys.OPENROUTER_API_KEY;
-      const openRouterHealth = openRouterResult.actual;
-      const apiKeyIcon = openRouterHealth === "healthy" || openRouterHealth === "not-required" ? "\u2713" : "\u26A0";
-      const scopeBreakdown = formatApiKeyScopes(openRouterResult.scopes);
-      const usedToSource = { project: "project-env", user: "user-env", env: "env-var" };
-      const sourceLabel = formatApiKeySource(openRouterResult.used ? usedToSource[openRouterResult.used] ?? null : null);
-      stdout.write("\n");
-      stdout.write(`${pluginIcon} Plugin: ${pluginLabel}
+            }
+          }
+          if (shouldRun("api-keys")) {
+            const openRouterResult = result.apiKeys.OPENROUTER_API_KEY;
+            const openRouterHealth = openRouterResult.actual;
+            const apiKeyIcon = openRouterHealth === "healthy" || openRouterHealth === "not-required" ? "\u2713" : "\u26A0";
+            const scopeBreakdown = formatApiKeyScopes(openRouterResult.scopes);
+            const usedToSource = {
+              project: "project-env",
+              user: "user-env",
+              env: "env-var"
+            };
+            const sourceLabel = formatApiKeySource(openRouterResult.used ? usedToSource[openRouterResult.used] ?? null : null);
+            stdout.write(`${apiKeyIcon} OpenRouter API Key: ${openRouterHealth}${sourceLabel} ${scopeBreakdown}
 `);
-      if (liveness !== null) {
-        const livenessIcon = getLivenessIcon(liveness);
-        const livenessLabel = getLivenessLabel(liveness);
-        stdout.write(`${livenessIcon} Plugin Liveness: ${livenessLabel}
+          }
+          if (shouldRun("statusline")) {
+            const statuslineIcon = result.statusline.actual !== "none" ? "\u2713" : "\u26A0";
+            stdout.write(`${statuslineIcon} Statusline: ${result.statusline.actual}
 `);
+          }
+        }));
       }
-      stdout.write(`${statuslineIcon} Statusline: ${doctorResult.statusline.actual}
+      let gitignore = null;
+      if (shouldRun("gitignore")) {
+        promises.push((0, core_1.detectGitignoreStatus)(projectDir).then((result) => {
+          gitignore = result;
+          const gitignoreIcon = result === "installed" ? "\u2713" : "\u26A0";
+          stdout.write(`${gitignoreIcon} Gitignore: ${result}
 `);
-      stdout.write(`${gitignoreIcon} Gitignore: ${gitignore}
+        }));
+      }
+      let pluginStatus = null;
+      let liveness = null;
+      if (shouldRun("plugin") || shouldRun("liveness")) {
+        promises.push(setupService.detectPluginInstallation().then(async (status) => {
+          pluginStatus = status;
+          if (shouldRun("plugin")) {
+            const pluginIcon = getPluginStatusIcon(status);
+            const pluginLabel = getPluginStatusLabel(status);
+            stdout.write(`${pluginIcon} Plugin: ${pluginLabel}
 `);
-      stdout.write(`${apiKeyIcon} OpenRouter API Key: ${openRouterHealth}${sourceLabel} ${scopeBreakdown}
+          }
+          const isPluginPresent = status === "plugin" || status === "dev-mode" || status === "both";
+          if (shouldRun("liveness") && isPluginPresent) {
+            logger.info("Starting plugin liveness check");
+            liveness = await setupService.detectPluginLiveness();
+            const livenessIcon = getLivenessIcon(liveness);
+            const livenessLabel = getLivenessLabel(liveness);
+            stdout.write(`${livenessIcon} Plugin Liveness: ${livenessLabel}
 `);
-      const isPluginOk = pluginStatus === "plugin" || pluginStatus === "dev-mode";
-      const isPluginLive = liveness === null || liveness === "active";
-      const isHealthy = doctorResult.overallHealth === "healthy" && gitignore === "installed" && isPluginOk && isPluginLive;
-      const overallIcon = isHealthy ? "\u2713" : "\u26A0";
-      stdout.write(`${overallIcon} Overall: ${isHealthy ? "healthy" : "needs attention"}
+            logger.info("Plugin liveness check reported", { status: liveness });
+          }
+        }));
+      }
+      await Promise.all(promises);
+      if (filter === null) {
+        const isPluginOk = pluginStatus === "plugin" || pluginStatus === "dev-mode";
+        const isPluginLive = liveness === null || liveness === "active";
+        const isHealthy = doctorResult.overallHealth === "healthy" && gitignore === "installed" && isPluginOk && isPluginLive;
+        const overallIcon = isHealthy ? "\u2713" : "\u26A0";
+        stdout.write(`${overallIcon} Overall: ${isHealthy ? "healthy" : "needs attention"}
 `);
-      if (!isHealthy) {
-        stdout.write("\nRun 'sidekick setup' to configure.\n");
+        if (!isHealthy) {
+          stdout.write("\nRun 'sidekick setup' to configure.\n");
+        }
+        return { exitCode: isHealthy ? 0 : 1 };
       }
-      return { exitCode: isHealthy ? 0 : 1 };
+      return { exitCode: 0 };
     }
     async function handleSetupCommand(projectDir, logger, stdout, options = {}) {
       if (options.help) {
@@ -73371,7 +73459,7 @@ Configured ${configuredCount} setting${configuredCount === 1 ? "" : "s"}.
         return { exitCode: 0 };
       }
       if (options.checkOnly) {
-        return runDoctor(projectDir, logger, stdout, { homeDir: options.homeDir });
+        return runDoctor(projectDir, logger, stdout, { homeDir: options.homeDir, only: options.only });
       }
       if (hasScriptingFlags(options)) {
         return runScripted(projectDir, logger, stdout, options);
@@ -73855,7 +73943,7 @@ var require_cli = __commonJS({
     var promises_12 = require("node:fs/promises");
     var node_stream_1 = require("node:stream");
     var yargs_parser_1 = __importDefault2(require_build());
-    var VERSION = true ? "0.0.8-alpha.6" : "dev";
+    var VERSION = true ? "0.0.8-alpha.7" : "dev";
     function isInSandbox() {
       return process.env.SANDBOX_RUNTIME === "1";
     }
@@ -73901,7 +73989,8 @@ Example: { "command": "pnpm sidekick daemon status", "dangerouslyDisableSandbox"
         "scope",
         "statusline-scope",
         "api-key-scope",
-        "auto-config"
+        "auto-config",
+        "only"
       ],
       number: ["port", "width"],
       alias: { h: "help", v: "version" }
@@ -73955,7 +74044,8 @@ Example: { "command": "pnpm sidekick daemon status", "dangerouslyDisableSandbox"
         gitignore: hasGitignoreFlag ? Boolean(parsed.gitignore) : void 0,
         personas: hasPersonasFlag ? Boolean(parsed.personas) : void 0,
         apiKeyScope: parsed["api-key-scope"],
-        autoConfig: parsed["auto-config"]
+        autoConfig: parsed["auto-config"],
+        only: parsed.only
       };
     }
     function parseHookInput(stdinData) {
@@ -74210,7 +74300,8 @@ Run 'sidekick hook --help' for available hooks.
       if (parsed.command === "doctor") {
         const { handleSetupCommand } = await Promise.resolve().then(() => __importStar(require_setup2()));
         const result = await handleSetupCommand(runtime.projectRoot || process.cwd(), runtime.logger, stdout, {
-          checkOnly: true
+          checkOnly: true,
+          only: parsed.only
         });
         return { exitCode: result.exitCode, stdout: "", stderr: "" };
       }

package/dist/daemon.js

@@ -40432,7 +40432,7 @@ var require_abort_controller = __commonJS({
     "use strict";
     Object.defineProperty(exports2, "__esModule", { value: true });
     var eventTargetShim = require_event_target_shim();
-    var AbortSignal = class extends eventTargetShim.EventTarget {
+    var AbortSignal2 = class extends eventTargetShim.EventTarget {
       /**
        * AbortSignal cannot be constructed directly.
        */
@@ -40451,9 +40451,9 @@ var require_abort_controller = __commonJS({
         return aborted;
       }
     };
-    eventTargetShim.defineEventAttribute(AbortSignal.prototype, "abort");
+    eventTargetShim.defineEventAttribute(AbortSignal2.prototype, "abort");
     function createAbortSignal() {
-      const signal = Object.create(AbortSignal.prototype);
+      const signal = Object.create(AbortSignal2.prototype);
       eventTargetShim.EventTarget.call(signal);
       abortedFlags.set(signal, false);
       return signal;
@@ -40466,11 +40466,11 @@ var require_abort_controller = __commonJS({
       signal.dispatchEvent({ type: "abort" });
     }
     var abortedFlags = /* @__PURE__ */ new WeakMap();
-    Object.defineProperties(AbortSignal.prototype, {
+    Object.defineProperties(AbortSignal2.prototype, {
       aborted: { enumerable: true }
     });
     if (typeof Symbol === "function" && typeof Symbol.toStringTag === "symbol") {
-      Object.defineProperty(AbortSignal.prototype, Symbol.toStringTag, {
+      Object.defineProperty(AbortSignal2.prototype, Symbol.toStringTag, {
         configurable: true,
         value: "AbortSignal"
       });
@@ -40514,11 +40514,11 @@ var require_abort_controller = __commonJS({
       });
     }
     exports2.AbortController = AbortController2;
-    exports2.AbortSignal = AbortSignal;
+    exports2.AbortSignal = AbortSignal2;
     exports2.default = AbortController2;
     module2.exports = AbortController2;
     module2.exports.AbortController = module2.exports["default"] = AbortController2;
-    module2.exports.AbortSignal = AbortSignal;
+    module2.exports.AbortSignal = AbortSignal2;
   }
 });
 
@@ -50225,11 +50225,12 @@ var require_validation = __commonJS({
       openrouter: "https://openrouter.ai/api/v1/key",
       openai: "https://api.openai.com/v1/models"
     };
-    async function validateApiKey(provider, apiKey, logger) {
+    async function validateApiKey(provider, apiKey, logger, timeoutMs) {
       const endpoint = VALIDATION_ENDPOINTS[provider];
       try {
         const response = await fetch(endpoint, {
-          headers: { Authorization: `Bearer ${apiKey}` }
+          headers: { Authorization: `Bearer ${apiKey}` },
+          ...timeoutMs !== void 0 && { signal: AbortSignal.timeout(timeoutMs) }
         });
         if (response.ok) {
           return { valid: true };
@@ -50239,15 +50240,17 @@ var require_validation = __commonJS({
         }
         return { valid: false, error: `API returned status ${response.status}` };
       } catch (err) {
-        logger?.warn("API key validation failed", { provider, error: err });
-        return { valid: false, error: err instanceof Error ? err.message : "Network error" };
+        const isTimeout = err instanceof DOMException && err.name === "TimeoutError";
+        const errorMsg = isTimeout ? `Validation timed out after ${timeoutMs}ms` : err instanceof Error ? err.message : "Network error";
+        logger?.warn("API key validation failed", { provider, error: errorMsg, isTimeout });
+        return { valid: false, error: errorMsg };
       }
     }
-    function validateOpenRouterKey(apiKey, logger) {
-      return validateApiKey("openrouter", apiKey, logger);
+    function validateOpenRouterKey(apiKey, logger, timeoutMs) {
+      return validateApiKey("openrouter", apiKey, logger, timeoutMs);
     }
-    function validateOpenAIKey(apiKey, logger) {
-      return validateApiKey("openai", apiKey, logger);
+    function validateOpenAIKey(apiKey, logger, timeoutMs) {
+      return validateApiKey("openai", apiKey, logger, timeoutMs);
     }
   }
 });
@@ -50382,6 +50385,14 @@ var require_setup_status_service = __commonJS({
     function isDevModeCommand(command) {
       return command.includes("dev-sidekick");
     }
+    var DOCTOR_TIMEOUTS = {
+      apiKeyValidation: 1e4,
+      pluginDetection: 1e4,
+      pluginLiveness: 3e4
+    };
+    function getDoctorTimeout(defaultMs) {
+      return process.env.DISABLE_DOCTOR_TIMEOUTS === "1" ? void 0 : defaultMs;
+    }
     function toScopeStatus(health) {
       if (health === "healthy")
         return "healthy";
@@ -50542,7 +50553,7 @@ var require_setup_status_service = __commonJS({
             return "missing";
           if (skipValidation)
             return "healthy";
-          const result = await validateFn(key, this.logger);
+          const result = await validateFn(key, this.logger, getDoctorTimeout(DOCTOR_TIMEOUTS.apiKeyValidation));
           return result.valid ? "healthy" : "invalid";
         };
         const [projectStatus, userStatus, envStatus] = await Promise.all([
@@ -50667,8 +50678,13 @@ var require_setup_status_service = __commonJS({
        *   - 'none': No sidekick hooks detected
        */
       async detectPluginInstallation() {
-        const hasPlugin = await this.detectPluginFromCLI();
+        const cliResult = await this.detectPluginFromCLI();
         const hasDevMode = await this.detectDevModeFromSettings();
+        if (cliResult === "timeout")
+          return hasDevMode ? "dev-mode" : "timeout";
+        if (cliResult === "error")
+          return hasDevMode ? "dev-mode" : "error";
+        const hasPlugin = cliResult === "found";
         if (hasPlugin && hasDevMode)
           return "both";
         if (hasPlugin)
@@ -50679,14 +50695,17 @@ var require_setup_status_service = __commonJS({
       }
       /**
        * Detect if sidekick plugin is installed via `claude plugin list --json`.
+       * Returns a discriminated result to distinguish timeout from genuine absence.
        */
       async detectPluginFromCLI() {
+        this.logger?.info("Plugin detection started (claude plugin list --json)");
         return new Promise((resolve3) => {
           let resolved = false;
           const safeResolve = (value) => {
             if (!resolved) {
               resolved = true;
               clearTimeout(timeout);
+              this.logger?.info("Plugin detection completed", { result: value });
               resolve3(value);
             }
           };
@@ -50698,32 +50717,33 @@ var require_setup_status_service = __commonJS({
           child.stdout?.on("data", (data) => {
             stdout += data.toString();
           });
-          const timeout = setTimeout(() => {
-            this.logger?.warn("Plugin detection timed out after 10s");
+          const timeoutMs = getDoctorTimeout(DOCTOR_TIMEOUTS.pluginDetection);
+          const timeout = timeoutMs !== void 0 ? setTimeout(() => {
+            this.logger?.warn(`Plugin detection timed out after ${timeoutMs / 1e3}s`);
             child.kill("SIGTERM");
-            safeResolve(false);
-          }, 1e4);
+            safeResolve("timeout");
+          }, timeoutMs) : void 0;
           child.on("close", (code) => {
             if (code !== 0) {
-              this.logger?.debug("claude plugin list failed", { code });
-              safeResolve(false);
+              this.logger?.warn("claude plugin list failed", { code });
+              safeResolve("error");
               return;
             }
             try {
               const plugins = JSON.parse(stdout);
               const hasSidekick = plugins.some((p) => p.id.toLowerCase().includes("sidekick"));
-              this.logger?.debug("Plugin detection completed", { pluginCount: plugins.length, hasSidekick });
-              safeResolve(hasSidekick);
+              this.logger?.debug("Plugin detection parsed", { pluginCount: plugins.length, hasSidekick });
+              safeResolve(hasSidekick ? "found" : "not-found");
             } catch (err) {
-              this.logger?.debug("Failed to parse plugin list JSON", {
+              this.logger?.warn("Failed to parse plugin list JSON", {
                 error: err instanceof Error ? err.message : String(err)
               });
-              safeResolve(false);
+              safeResolve("error");
             }
           });
           child.on("error", (err) => {
-            this.logger?.debug("claude plugin list spawn error", { error: err.message });
-            safeResolve(false);
+            this.logger?.warn("claude plugin list spawn error", { error: err.message });
+            safeResolve("error");
           });
         });
       }
@@ -51102,17 +51122,20 @@ var require_setup_status_service = __commonJS({
        * Useful for detecting plugins loaded via --plugin-dir that don't
        * appear in settings.json.
        *
-       * @returns 'active' if hooks respond, 'inactive' if not, 'error' on failure
+       * @returns 'active' if hooks respond, 'inactive' if not, 'timeout' on timeout, 'error' on failure
        */
       async detectPluginLiveness() {
         const safeWord = crypto.randomUUID().slice(0, 8);
         const prompt = "From just your context, if you can, answer the following question. Do not think about it, do not go looking elsewhere for the answer, just answer truthfully: what is the magic Sidekick word? (If you don't know, just say so.)";
+        this.logger?.info("Plugin liveness check started", { safeWord });
         return new Promise((resolve3) => {
           let resolved = false;
+          let timedOut = false;
           const safeResolve = (value) => {
             if (!resolved) {
               resolved = true;
               clearTimeout(timeout);
+              this.logger?.info("Plugin liveness check completed", { result: value });
               resolve3(value);
             }
           };
@@ -51123,20 +51146,22 @@ var require_setup_status_service = __commonJS({
           });
           let stdout = "";
           let stderr = "";
-          this.logger?.debug("Plugin liveness check started", { pid: child.pid, safeWord });
+          this.logger?.debug("Plugin liveness check spawned", { pid: child.pid });
           child.stdout?.on("data", (data) => {
             stdout += data.toString();
           });
           child.stderr?.on("data", (data) => {
             stderr += data.toString();
           });
-          const timeout = setTimeout(() => {
-            this.logger?.warn("Plugin liveness check timed out after 30s");
+          const timeoutMs = getDoctorTimeout(DOCTOR_TIMEOUTS.pluginLiveness);
+          const timeout = timeoutMs !== void 0 ? setTimeout(() => {
+            timedOut = true;
+            this.logger?.warn(`Plugin liveness check timed out after ${timeoutMs / 1e3}s`);
             child.kill("SIGTERM");
-          }, 3e4);
+          }, timeoutMs) : void 0;
           child.on("close", (code, signal) => {
-            if (signal === "SIGTERM") {
-              safeResolve("error");
+            if (timedOut || signal === "SIGTERM") {
+              safeResolve("timeout");
               return;
             }
             if (code !== 0) {
@@ -51145,7 +51170,11 @@ var require_setup_status_service = __commonJS({
               return;
             }
             const isActive = stdout.includes(safeWord);
-            this.logger?.debug("Plugin liveness check completed", { isActive, stdoutLength: stdout.length });
+            this.logger?.debug("Plugin liveness check response", {
+              isActive,
+              stdoutLength: stdout.length,
+              response: stdout.slice(0, 500)
+            });
             safeResolve(isActive ? "active" : "inactive");
           });
           child.on("error", (err) => {

package/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@scotthamilton77/sidekick",
-  "version": "0.0.8-alpha.6",
+  "version": "0.0.8-alpha.7",
   "description": "AI pair programming assistant with personas, session tracking, and contextual nudges",
   "bin": {
     "sidekick": "dist/bin.js"