diff --git a/web/src/server/fwd.ts b/web/src/server/fwd.ts
index c8e36688..6194acfc 100755
--- a/web/src/server/fwd.ts
+++ b/web/src/server/fwd.ts
@@ -17,6 +17,7 @@ import chalk from 'chalk';
 import { PtyManager } from './pty/index.js';
 import { VERSION, BUILD_DATE, GIT_COMMIT } from './version.js';
 import { createLogger, closeLogger } from './utils/logger.js';
+import { generateSessionName } from './utils/session-naming.js';
 
 const logger = createLogger('fwd');
 
@@ -79,8 +80,8 @@ export async function startVibeTunnelForward(args: string[]) {
   const ptyManager = new PtyManager(controlPath);
 
   try {
-    // Create the session
-    const sessionName = `fwd_${command[0]}_${Date.now()}`;
+    // Create a human-readable session name
+    const sessionName = generateSessionName(command, cwd);
 
     // Pre-generate session ID if not provided
     const finalSessionId = sessionId || `fwd_${Date.now()}`;
diff --git a/web/src/server/routes/sessions.ts b/web/src/server/routes/sessions.ts
index 04fddf87..6c0de36a 100644
--- a/web/src/server/routes/sessions.ts
+++ b/web/src/server/routes/sessions.ts
@@ -7,6 +7,7 @@ import { RemoteRegistry } from '../services/remote-registry.js';
 import { ActivityMonitor } from '../services/activity-monitor.js';
 import { cellsToText } from '../../shared/terminal-text-formatter.js';
 import { createLogger } from '../utils/logger.js';
+import { generateSessionName } from '../utils/session-naming.js';
 import chalk from 'chalk';
 import * as fs from 'fs';
 import * as path from 'path';
@@ -186,7 +187,8 @@ export function createSessionRoutes(config: SessionRoutesConfig): Router {
         try {
           // Generate session ID
           const sessionId = generateSessionId();
-          const sessionName = name || `session_${Date.now()}`;
+          const sessionName =
+            name || generateSessionName(command, resolvePath(workingDir, process.cwd()));
 
           // Request Mac app to spawn terminal
           logger.log(
@@ -227,9 +229,8 @@ export function createSessionRoutes(config: SessionRoutesConfig): Router {
       }
 
       // Create local session
-      const sessionName =
-        name || `session_${Date.now()}_${Math.random().toString(36).substr(2, 9)}`;
       const cwd = resolvePath(workingDir, process.cwd());
+      const sessionName = name || generateSessionName(command, cwd);
 
       logger.log(chalk.blue(`creating session: ${command.join(' ')} in ${cwd}`));
 
diff --git a/web/src/server/utils/session-naming.ts b/web/src/server/utils/session-naming.ts
new file mode 100644
index 00000000..58cefa87
--- /dev/null
+++ b/web/src/server/utils/session-naming.ts
@@ -0,0 +1,49 @@
+import * as path from 'path';
+import * as os from 'os';
+
+/**
+ * Abbreviate a file path to make it more readable
+ * Examples:
+ *   /Users/john/Projects/myproject -> ~/Projects/myproject
+ *   /Users/john/Development/vibetunnel/web -> ~/Dev/vibetunnel/web
+ *   /very/long/path/to/some/directory -> …/some/directory
+ */
+export function abbreviatePath(fullPath: string): string {
+  if (!fullPath) return '';
+
+  const homedir = os.homedir();
+  let abbreviated = fullPath;
+
+  // Replace home directory with ~
+  if (fullPath.startsWith(homedir)) {
+    abbreviated = '~' + fullPath.slice(homedir.length);
+  }
+
+  // Common abbreviations
+  abbreviated = abbreviated
+    .replace('/Development/', '/Dev/')
+    .replace('/Documents/', '/Docs/')
+    .replace('/Applications/', '/Apps/');
+
+  // If still long, show only last 2 path components
+  const parts = abbreviated.split('/').filter((p) => p);
+  if (parts.length > 3) {
+    return '…/' + parts.slice(-2).join('/');
+  }
+
+  return abbreviated;
+}
+
+/**
+ * Generate a human-readable session name
+ * Format: commandName (abbreviatedPath)
+ * Examples:
+ *   claude (~/Dev/vibetunnel/web)
+ *   bash (~/Projects/myapp)
+ *   python3 (~)
+ */
+export function generateSessionName(command: string[], workingDir: string): string {
+  const commandName = path.basename(command[0]);
+  const abbrevCwd = abbreviatePath(workingDir);
+  return abbrevCwd ? `${commandName} (${abbrevCwd})` : commandName;
+}