diff --git a/src/cliproxy/binary/downloader.ts b/src/cliproxy/binary/downloader.ts
index 9ab46e60..b06a4e08 100644
--- a/src/cliproxy/binary/downloader.ts
+++ b/src/cliproxy/binary/downloader.ts
@@ -1,6 +1,7 @@
 /**
  * Binary Downloader
  * Handles downloading files with retry logic, progress tracking, and redirect following.
+ * Robust handling for transient network errors (socket hang up, ECONNRESET, etc.)
  */
 
 import * as fs from 'fs';
@@ -14,40 +15,111 @@ export interface DownloaderConfig {
   maxRetries: number;
   /** Enable verbose logging */
   verbose: boolean;
+  /** Timeout in milliseconds (default: 120000 for large files) */
+  timeout?: number;
 }
 
 const DEFAULT_CONFIG: DownloaderConfig = {
-  maxRetries: 3,
+  maxRetries: 5,
   verbose: false,
+  timeout: 120000, // 2 minutes for large binaries
 };
 
+/** Error types for categorized handling */
+export type NetworkErrorType = 'socket' | 'timeout' | 'http' | 'redirect' | 'unknown';
+
+/** Categorize error for appropriate retry/reporting */
+export function categorizeError(error: Error): NetworkErrorType {
+  const msg = error.message.toLowerCase();
+  if (msg.includes('socket hang up') || msg.includes('econnreset') || msg.includes('epipe')) {
+    return 'socket';
+  }
+  if (msg.includes('timeout') || msg.includes('etimedout')) {
+    return 'timeout';
+  }
+  if (msg.includes('http ')) {
+    return 'http';
+  }
+  if (msg.includes('redirect')) {
+    return 'redirect';
+  }
+  return 'unknown';
+}
+
+/** Get user-friendly error message */
+export function getErrorMessage(error: Error, attempt: number, maxAttempts: number): string {
+  const type = categorizeError(error);
+  const prefix = `[Attempt ${attempt}/${maxAttempts}]`;
+
+  switch (type) {
+    case 'socket':
+      return `${prefix} Connection dropped (socket hang up) - retrying with fresh connection...`;
+    case 'timeout':
+      return `${prefix} Download timed out - retrying with extended timeout...`;
+    case 'http':
+      return `${prefix} Server error: ${error.message}`;
+    case 'redirect':
+      return `${prefix} Redirect failed: ${error.message}`;
+    default:
+      return `${prefix} Network error: ${error.message}`;
+  }
+}
+
+/** Check if error is retryable */
+export function isRetryableError(error: Error): boolean {
+  const type = categorizeError(error);
+  // Retry socket errors, timeouts, and unknown errors
+  if (type === 'socket' || type === 'timeout' || type === 'unknown') {
+    return true;
+  }
+  if (type === 'http') {
+    const msg = error.message;
+    // Retry 5xx server errors and 429 rate limit (HTTP 5xx matches 500, 502, 503, 504, etc.)
+    return msg.includes('HTTP 5') || msg.includes('HTTP 429');
+  }
+  return false;
+}
+
 /**
  * Download file from URL with progress tracking
+ * @param timeout Timeout in ms (default 120000 for large files)
  */
 export function downloadFile(
   url: string,
   destPath: string,
   onProgress?: ProgressCallback,
-  verbose = false
+  verbose = false,
+  timeout = 120000
 ): Promise<void> {
   return new Promise((resolve, reject) => {
+    let resolved = false;
+
+    const cleanup = (err?: Error) => {
+      if (resolved) return;
+      resolved = true;
+      fs.unlink(destPath, () => {}); // Cleanup partial file
+      reject(err || new Error('Download aborted'));
+    };
+
     const handleResponse = (res: http.IncomingMessage) => {
       // Handle redirects (GitHub releases use 302)
       if (res.statusCode === 301 || res.statusCode === 302) {
         const redirectUrl = res.headers.location;
         if (!redirectUrl) {
-          reject(new Error('Redirect without location header'));
+          cleanup(new Error('Redirect without location header'));
           return;
         }
         if (verbose) {
           console.error(`[cliproxy] Following redirect: ${redirectUrl}`);
         }
-        downloadFile(redirectUrl, destPath, onProgress, verbose).then(resolve).catch(reject);
+        downloadFile(redirectUrl, destPath, onProgress, verbose, timeout)
+          .then(resolve)
+          .catch(reject);
         return;
       }
 
       if (res.statusCode !== 200) {
-        reject(new Error(`HTTP ${res.statusCode}: ${res.statusMessage}`));
+        cleanup(new Error(`HTTP ${res.statusCode}: ${res.statusMessage}`));
         return;
       }
 
@@ -70,58 +142,94 @@ export function downloadFile(
       res.pipe(fileStream);
 
       fileStream.on('finish', () => {
+        if (resolved) return;
+        resolved = true;
         fileStream.close();
         resolve();
       });
 
-      fileStream.on('error', (err) => {
-        fs.unlink(destPath, () => {}); // Cleanup partial file
-        reject(err);
-      });
-
-      res.on('error', (err) => {
-        fs.unlink(destPath, () => {});
-        reject(err);
-      });
+      fileStream.on('error', cleanup);
+      res.on('error', cleanup);
     };
 
     const protocol = url.startsWith('https') ? https : http;
-    const req = protocol.get(url, handleResponse);
 
-    req.on('error', reject);
-    req.setTimeout(60000, () => {
+    // Use agent: false to prevent connection pooling (allows process to exit)
+    const options = {
+      headers: {
+        'User-Agent': 'CCS-CLIProxyPlus-Downloader/1.0',
+      },
+      agent: false, // Disable connection pooling for clean exit
+    };
+
+    const req = protocol.get(url, options, handleResponse);
+
+    req.on('error', (err) => {
+      if (!resolved) {
+        cleanup(err);
+      }
+    });
+
+    req.setTimeout(timeout, () => {
       req.destroy();
-      reject(new Error('Download timeout (60s)'));
+      if (!resolved) {
+        cleanup(new Error(`Download timeout (${timeout / 1000}s)`));
+      }
     });
   });
 }
 
 /**
  * Download file with retry logic and exponential backoff
+ * Uses smarter backoff for socket errors (longer delays)
  */
 export async function downloadWithRetry(
   url: string,
   destPath: string,
   config: Partial<DownloaderConfig> = {}
 ): Promise<DownloadResult> {
-  const { maxRetries, verbose } = { ...DEFAULT_CONFIG, ...config };
-  let lastError = '';
+  const { maxRetries, verbose, timeout } = { ...DEFAULT_CONFIG, ...config };
+  let lastError: Error | null = null;
   let retries = 0;
+  let currentTimeout = timeout || 120000;
 
   while (retries < maxRetries) {
     try {
-      await downloadFile(url, destPath, undefined, verbose);
+      await downloadFile(url, destPath, undefined, verbose, currentTimeout);
       return { success: true, filePath: destPath, retries };
     } catch (error) {
       const err = error as Error;
-      lastError = err.message;
+      lastError = err;
       retries++;
 
-      if (retries < maxRetries) {
-        // Exponential backoff: 1s, 2s, 4s
-        const delay = Math.pow(2, retries - 1) * 1000;
+      // Check if error is retryable
+      if (!isRetryableError(err)) {
         if (verbose) {
-          console.error(`[cliproxy] Retry ${retries}/${maxRetries} after ${delay}ms: ${lastError}`);
+          console.error(`[cliproxy] Non-retryable error: ${err.message}`);
+        }
+        break;
+      }
+
+      if (retries < maxRetries) {
+        const errorType = categorizeError(err);
+        // Socket errors: longer backoff (2s, 4s, 8s, 16s, 32s)
+        // Timeout errors: increase timeout and use standard backoff
+        // Other errors: standard exponential backoff (1s, 2s, 4s...)
+        let delay: number;
+
+        if (errorType === 'socket') {
+          delay = Math.pow(2, retries) * 1000; // 2s, 4s, 8s, 16s, 32s
+        } else if (errorType === 'timeout') {
+          delay = Math.pow(2, retries - 1) * 1000;
+          currentTimeout = Math.min(currentTimeout * 1.5, 300000); // Increase timeout up to 5 min
+        } else {
+          delay = Math.pow(2, retries - 1) * 1000;
+        }
+
+        // Log with user-friendly message
+        console.error(`[cliproxy] ${getErrorMessage(err, retries, maxRetries)}`);
+        if (verbose) {
+          console.error(`[cliproxy] Waiting ${delay}ms before retry...`);
         }
         await sleep(delay);
       }
@@ -130,16 +238,18 @@ export async function downloadWithRetry(
 
   return {
     success: false,
-    error: `Download failed after ${retries} attempts: ${lastError}`,
+    error: `Download failed after ${retries} attempts: ${lastError?.message || 'Unknown error'}`,
     retries,
   };
 }
 
 /**
- * Fetch text content from URL
+ * Fetch text content from URL (single attempt)
  */
-export function fetchText(url: string, verbose = false): Promise<string> {
+function fetchTextOnce(url: string, verbose = false, timeout = 30000): Promise<string> {
   return new Promise((resolve, reject) => {
+    let resolved = false;
+
     const handleResponse = (res: http.IncomingMessage) => {
       // Handle redirects
       if (res.statusCode === 301 || res.statusCode === 302) {
@@ -148,7 +258,7 @@ export function fetchText(url: string, verbose = false): Promise<string> {
           reject(new Error('Redirect without location header'));
           return;
         }
-        fetchText(redirectUrl, verbose).then(resolve).catch(reject);
+        fetchTextOnce(redirectUrl, verbose, timeout).then(resolve).catch(reject);
         return;
       }
 
@@ -159,30 +269,90 @@ export function fetchText(url: string, verbose = false): Promise<string> {
 
       let data = '';
       res.on('data', (chunk) => (data += chunk));
-      res.on('end', () => resolve(data));
-      res.on('error', reject);
+      res.on('end', () => {
+        if (!resolved) {
+          resolved = true;
+          resolve(data);
+        }
+      });
+      res.on('error', (err) => {
+        if (!resolved) {
+          resolved = true;
+          reject(err);
+        }
+      });
     };
 
     const protocol = url.startsWith('https') ? https : http;
-    const req = protocol.get(url, handleResponse);
-    req.on('error', reject);
-    req.setTimeout(30000, () => {
+    const options = {
+      headers: {
+        'User-Agent': 'CCS-CLIProxyPlus-Downloader/1.0',
+      },
+      agent: false, // Disable connection pooling for clean exit
+    };
+
+    const req = protocol.get(url, options, handleResponse);
+    req.on('error', (err) => {
+      if (!resolved) {
+        resolved = true;
+        reject(err);
+      }
+    });
+    req.setTimeout(timeout, () => {
       req.destroy();
-      reject(new Error('Request timeout (30s)'));
+      if (!resolved) {
+        resolved = true;
+        reject(new Error(`Request timeout (${timeout / 1000}s)`));
+      }
     });
   });
 }
 
 /**
- * Fetch JSON from URL (for GitHub API)
+ * Fetch text content from URL with retry logic
  */
-export function fetchJson(url: string, verbose = false): Promise<Record<string, unknown>> {
+export async function fetchText(url: string, verbose = false, maxRetries = 3): Promise<string> {
+  let lastError: Error | null = null;
+
+  for (let attempt = 1; attempt <= maxRetries; attempt++) {
+    try {
+      return await fetchTextOnce(url, verbose);
+    } catch (error) {
+      const err = error as Error;
+      lastError = err;
+
+      if (!isRetryableError(err) || attempt === maxRetries) {
+        break;
+      }
+
+      const delay = Math.pow(2, attempt - 1) * 1000;
+      if (verbose) {
+        console.error(`[cliproxy] fetchText retry ${attempt}/${maxRetries}: ${err.message}`);
+      }
+      await sleep(delay);
+    }
+  }
+
+  throw lastError || new Error('fetchText failed');
+}
+
+/**
+ * Fetch JSON from URL (single attempt, for GitHub API)
+ */
+function fetchJsonOnce(
+  url: string,
+  verbose = false,
+  timeout = 15000
+): Promise<Record<string, unknown>> {
   return new Promise((resolve, reject) => {
-    const options = {
+    let resolved = false;
+
+    const options: https.RequestOptions = {
       headers: {
         'User-Agent': 'CCS-CLIProxyPlus-Updater/1.0',
         Accept: 'application/vnd.github.v3+json',
       },
+      agent: false, // Disable connection pooling for clean exit
     };
 
     const handleResponse = (res: http.IncomingMessage) => {
@@ -192,7 +362,7 @@ export function fetchJson(url: string, verbose = false): Promise<Record<string,
           reject(new Error('Redirect without location header'));
           return;
         }
-        fetchJson(redirectUrl, verbose).then(resolve).catch(reject);
+        fetchJsonOnce(redirectUrl, verbose, timeout).then(resolve).catch(reject);
         return;
       }
 
@@ -204,24 +374,71 @@ export function fetchJson(url: string, verbose = false): Promise<Record<string,
       let data = '';
       res.on('data', (chunk) => (data += chunk));
       res.on('end', () => {
+        if (resolved) return;
+        resolved = true;
         try {
           resolve(JSON.parse(data));
         } catch {
           reject(new Error('Invalid JSON from GitHub API'));
         }
       });
-      res.on('error', reject);
+      res.on('error', (err) => {
+        if (!resolved) {
+          resolved = true;
+          reject(err);
+        }
+      });
     };
 
     const req = https.get(url, options, handleResponse);
-    req.on('error', reject);
-    req.setTimeout(10000, () => {
+    req.on('error', (err) => {
+      if (!resolved) {
+        resolved = true;
+        reject(err);
+      }
+    });
+    req.setTimeout(timeout, () => {
       req.destroy();
-      reject(new Error('GitHub API timeout (10s)'));
+      if (!resolved) {
+        resolved = true;
+        reject(new Error(`GitHub API timeout (${timeout / 1000}s)`));
+      }
     });
   });
 }
 
+/**
+ * Fetch JSON from URL (for GitHub API) with retry logic
+ */
+export async function fetchJson(
+  url: string,
+  verbose = false,
+  maxRetries = 3
+): Promise<Record<string, unknown>> {
+  let lastError: Error | null = null;
+
+  for (let attempt = 1; attempt <= maxRetries; attempt++) {
+    try {
+      return await fetchJsonOnce(url, verbose);
+    } catch (error) {
+      const err = error as Error;
+      lastError = err;
+
+      if (!isRetryableError(err) || attempt === maxRetries) {
+        break;
+      }
+
+      const delay = Math.pow(2, attempt - 1) * 1000;
+      if (verbose) {
+        console.error(`[cliproxy] GitHub API retry ${attempt}/${maxRetries}: ${err.message}`);
+      }
+      await sleep(delay);
+    }
+  }
+
+  throw lastError || new Error('fetchJson failed');
+}
+
 /**
  * Sleep helper
  */
diff --git a/src/cliproxy/cliproxy-executor.ts b/src/cliproxy/cliproxy-executor.ts
index 16e08434..6152be27 100644
--- a/src/cliproxy/cliproxy-executor.ts
+++ b/src/cliproxy/cliproxy-executor.ts
@@ -424,13 +424,17 @@ export async function execClaudeWithCLIProxy(
       if (proxyStatus.running && proxyStatus.verified) {
         // Healthy proxy found - join it
         if (proxyStatus.pid) {
-          sessionId = reclaimOrphanedProxy(cfg.port, proxyStatus.pid) ?? undefined;
+          sessionId = reclaimOrphanedProxy(cfg.port, proxyStatus.pid, verbose) ?? undefined;
         }
         if (sessionId) {
           console.log(info(`Joined existing CLIProxy on port ${cfg.port} (${proxyStatus.method})`));
         } else {
-          // Failed to register session, but proxy is running - continue anyway
-          log(`Failed to register session but proxy is healthy, continuing...`);
+          // Failed to register session - proxy is running but we can't track it
+          // This happens when port-process detection fails (permissions, platform issues)
+          console.log(
+            info(`Using existing CLIProxy on port ${cfg.port} (session tracking unavailable)`)
+          );
+          log(`PID=${proxyStatus.pid ?? 'unknown'}, session registration skipped`);
         }
         return; // Exit lock early, skip spawning
       }
@@ -441,7 +445,7 @@ export async function execClaudeWithCLIProxy(
         const becameHealthy = await waitForProxyHealthy(cfg.port, cfg.timeout);
         if (becameHealthy) {
           if (proxyStatus.pid) {
-            sessionId = reclaimOrphanedProxy(cfg.port, proxyStatus.pid) ?? undefined;
+            sessionId = reclaimOrphanedProxy(cfg.port, proxyStatus.pid, verbose) ?? undefined;
           }
           console.log(info(`Joined CLIProxy after startup wait`));
           return; // Exit lock early
@@ -459,7 +463,7 @@ export async function execClaudeWithCLIProxy(
         // Last resort: try HTTP health check (handles Windows PID-XXXXX case)
         const isActuallyOurs = await waitForProxyHealthy(cfg.port, 1000);
         if (isActuallyOurs) {
-          sessionId = reclaimOrphanedProxy(cfg.port, proxyStatus.blocker.pid) ?? undefined;
+          sessionId = reclaimOrphanedProxy(cfg.port, proxyStatus.blocker.pid, verbose) ?? undefined;
           console.log(info(`Reclaimed CLIProxy with unrecognized process name`));
           return;
         }
diff --git a/src/cliproxy/proxy-detector.ts b/src/cliproxy/proxy-detector.ts
index b2afe545..1a7bc812 100644
--- a/src/cliproxy/proxy-detector.ts
+++ b/src/cliproxy/proxy-detector.ts
@@ -73,12 +73,25 @@ export async function detectRunningProxy(
     // Proxy is running and responsive
     // Try to get PID from session lock if available
     const lock = getExistingProxy(port);
-    log(`HTTP check passed, proxy healthy (PID: ${lock?.pid ?? 'unknown'})`);
+    let pid = lock?.pid;
+
+    // If no PID from session lock, try port-process detection
+    // This handles orphaned proxies (running but no sessions.json)
+    if (!pid) {
+      log('No PID from session lock, checking port process...');
+      const portProcess = await getPortProcess(port);
+      if (portProcess) {
+        pid = portProcess.pid;
+        log(`Got PID from port process: ${pid}`);
+      }
+    }
+
+    log(`HTTP check passed, proxy healthy (PID: ${pid ?? 'unknown'})`);
     return {
       running: true,
       verified: true,
       method: 'http',
-      pid: lock?.pid,
+      pid,
       sessionCount: lock?.sessions?.length,
     };
   }