diff --git a/cli/src/connection.rs b/cli/src/connection.rs
index d532943..f749dbb 100644
--- a/cli/src/connection.rs
+++ b/cli/src/connection.rs
@@ -119,7 +119,7 @@ fn get_pid_path(session: &str) -> PathBuf {
 }
 
 /// Clean up stale socket and PID files for a session
-fn cleanup_stale_files(session: &str) {
+pub fn cleanup_stale_files(session: &str) {
     let pid_path = get_pid_path(session);
     let _ = fs::remove_file(&pid_path);
     let stream_path = get_socket_dir().join(format!("{}.stream", session));
@@ -429,6 +429,21 @@ pub fn ensure_daemon(session: &str, opts: &DaemonOptions) -> Result<DaemonResult
                     let _ = stderr.read_to_string(&mut stderr_output);
                 }
                 let stderr_trimmed = stderr_output.trim();
+
+                // If the daemon failed because another instance won the bind
+                // race ("Address already in use"), check whether that winner is
+                // now accepting connections and piggyback on it.
+                if stderr_trimmed.contains("Address already in use")
+                    || stderr_trimmed.contains("Failed to bind")
+                {
+                    thread::sleep(Duration::from_millis(200));
+                    if daemon_ready(session) {
+                        return Ok(DaemonResult {
+                            already_running: true,
+                        });
+                    }
+                }
+
                 if !stderr_trimmed.is_empty() {
                     let msg = if stderr_trimmed.len() > 500 {
                         let mut end = 500;
diff --git a/cli/src/main.rs b/cli/src/main.rs
index 979f592..e43d6a7 100644
--- a/cli/src/main.rs
+++ b/cli/src/main.rs
@@ -21,7 +21,7 @@ use windows_sys::Win32::Foundation::CloseHandle;
 use windows_sys::Win32::System::Threading::{OpenProcess, PROCESS_QUERY_LIMITED_INFORMATION};
 
 use commands::{gen_id, parse_command, ParseError};
-use connection::{ensure_daemon, get_socket_dir, send_command, DaemonOptions};
+use connection::{cleanup_stale_files, ensure_daemon, get_socket_dir, send_command, DaemonOptions};
 use flags::{clean_args, parse_flags, Flags};
 use install::run_install;
 use output::{
@@ -380,7 +380,7 @@ fn run_dashboard_stop(json_mode: bool) {
 
 fn run_close_all(flags: &Flags) {
     let socket_dir = get_socket_dir();
-    let mut sessions: Vec<String> = Vec::new();
+    let mut sessions: Vec<(String, u32)> = Vec::new();
 
     if let Ok(entries) = fs::read_dir(&socket_dir) {
         for entry in entries.flatten() {
@@ -409,9 +409,33 @@ fn run_close_all(flags: &Flags) {
                             }
                         };
                         if running {
-                            sessions.push(session_name.to_string());
+                            sessions.push((session_name.to_string(), pid));
+                        } else {
+                            // Process is gone but stale files remain; clean them up
+                            cleanup_stale_files(session_name);
                         }
                     }
+                } else {
+                    // PID file exists but is unreadable; clean up stale files
+                    cleanup_stale_files(session_name);
+                }
+            }
+        }
+    }
+
+    // Also scan for orphaned .sock files without corresponding .pid files
+    #[cfg(unix)]
+    if let Ok(entries) = fs::read_dir(&socket_dir) {
+        for entry in entries.flatten() {
+            let name = entry.file_name().to_string_lossy().to_string();
+            if let Some(session_name) = name.strip_suffix(".sock") {
+                if session_name.is_empty() {
+                    continue;
+                }
+                let pid_path = socket_dir.join(format!("{}.pid", session_name));
+                if !pid_path.exists() {
+                    // Orphaned socket file with no PID file; remove it
+                    cleanup_stale_files(session_name);
                 }
             }
         }
@@ -432,7 +456,7 @@ fn run_close_all(flags: &Flags) {
     let mut closed: Vec<String> = Vec::new();
     let mut failed: Vec<(String, String)> = Vec::new();
 
-    for session in &sessions {
+    for (session, pid) in &sessions {
         let cmd = json!({ "id": gen_id(), "action": "close" });
         match send_command(cmd, session) {
             Ok(resp) if resp.success => closed.push(session.clone()),
@@ -440,7 +464,25 @@ fn run_close_all(flags: &Flags) {
                 let err = resp.error.unwrap_or_else(|| "Unknown error".to_string());
                 failed.push((session.clone(), err));
             }
-            Err(e) => failed.push((session.clone(), e.to_string())),
+            Err(_) => {
+                // Daemon is unreachable despite its process existing.
+                // Force-kill the process and clean up stale files so future
+                // sessions are not poisoned.
+                #[cfg(unix)]
+                unsafe {
+                    libc::kill(*pid as i32, libc::SIGKILL);
+                }
+                #[cfg(windows)]
+                unsafe {
+                    let handle = OpenProcess(1, 0, *pid); // PROCESS_TERMINATE = 1
+                    if handle != 0 {
+                        windows_sys::Win32::System::Threading::TerminateProcess(handle, 1);
+                        CloseHandle(handle);
+                    }
+                }
+                cleanup_stale_files(session);
+                closed.push(session.clone());
+            }
         }
     }