diff --git a/docs/getting-started.md b/docs/getting-started.md
index a7c52547..0a5dd318 100644
--- a/docs/getting-started.md
+++ b/docs/getting-started.md
@@ -62,7 +62,7 @@ nightcrow update
 nightcrow update --version 0.1.1
 ```
 
-By default this downloads and verifies the latest binary from the official GitHub Release. Use `--version VER` to roll back to a published patch. Use `--path DIR` for a local checkout or `--git URL` for another source repository; those explicit development modes require Rust and run a locked, forced `cargo install`. Restart the session after updating so the daemon and its panes use the new binary. On Windows, `update` moves the installed executable aside before replacing it.
+By default this downloads and verifies the latest binary from the official GitHub Release. Use `--version VER` to roll back to a published patch. Use `--path DIR` for a local checkout or `--git URL` for another source repository; those explicit development modes require Rust and run a locked, forced `cargo install`. Restart a running session after updating with `nightcrow stop`, then start nightcrow again so the daemon and its panes use the new binary. On Windows, `update` moves the installed executable aside before replacing it; if that parked copy is still in use, cleanup waits for the session or updater to exit. The new binary is already installed, so a second `update` is not needed.
 
 ## Building and testing
 
diff --git a/src/cli/stop.rs b/src/cli/stop.rs
index 71b1ce6c..75c1bf98 100644
--- a/src/cli/stop.rs
+++ b/src/cli/stop.rs
@@ -12,6 +12,7 @@ use crate::daemon::protocol::ServerMessage;
 // bounded cleanup of a full configured session while still rejecting a lost
 // request instead of waiting forever.
 const SHUTDOWN_ACK_TIMEOUT: Duration = Duration::from_secs(20);
+const SHUTDOWN_POLL_INTERVAL: Duration = Duration::from_millis(25);
 
 /// Send a graceful shutdown request to a running daemon.
 pub(crate) fn run_stop(socket: Option<PathBuf>) -> Result<()> {
@@ -41,9 +42,22 @@ pub(crate) fn run_stop(socket: Option<PathBuf>) -> Result<()> {
         .set_read_timeout(Some(SHUTDOWN_ACK_TIMEOUT))
         .context("setting the shutdown acknowledgment timeout")?;
 
-    wait_for_shutdown_ack(&mut stream, Instant::now() + SHUTDOWN_ACK_TIMEOUT)?;
+    let deadline = Instant::now() + SHUTDOWN_ACK_TIMEOUT;
+    wait_for_shutdown_ack(&mut stream, deadline)?;
+    wait_for_daemon_exit(&path, deadline)?;
 
-    println!("nightcrow: daemon is shutting down");
+    println!("nightcrow: daemon stopped");
+    Ok(())
+}
+
+/// Wait until the daemon has dropped its socket and instance lock.
+fn wait_for_daemon_exit(path: &std::path::Path, deadline: Instant) -> Result<()> {
+    while path.exists() {
+        if Instant::now() >= deadline {
+            anyhow::bail!("timed out waiting for the daemon to stop");
+        }
+        std::thread::sleep(SHUTDOWN_POLL_INTERVAL);
+    }
     Ok(())
 }
 
diff --git a/src/cli/stop_tests.rs b/src/cli/stop_tests.rs
index 557def6f..d19dde5f 100644
--- a/src/cli/stop_tests.rs
+++ b/src/cli/stop_tests.rs
@@ -70,6 +70,38 @@ fn clean_eof_is_a_shutdown_acknowledgment() {
     assert!(wait_for_shutdown_ack(&mut Cursor::new(Vec::new()), future_deadline()).is_ok());
 }
 
+#[test]
+fn stop_waits_until_the_daemon_socket_is_released() {
+    let dir = tempfile::tempdir().unwrap();
+    let path = dir.path().join("daemon.sock");
+    std::fs::write(&path, b"socket").unwrap();
+    let release_path = path.clone();
+    let releaser = std::thread::spawn(move || {
+        std::thread::sleep(Duration::from_millis(50));
+        std::fs::remove_file(release_path).unwrap();
+    });
+
+    wait_for_daemon_exit(&path, future_deadline()).expect("waits for socket release");
+
+    releaser.join().unwrap();
+    assert!(!path.exists());
+}
+
+#[test]
+fn stop_fails_when_the_daemon_socket_is_not_released() {
+    let dir = tempfile::tempdir().unwrap();
+    let path = dir.path().join("daemon.sock");
+    std::fs::write(&path, b"socket").unwrap();
+
+    let error = wait_for_daemon_exit(&path, Instant::now()).expect_err("expired deadline");
+
+    assert!(
+        error
+            .to_string()
+            .contains("timed out waiting for the daemon to stop")
+    );
+}
+
 #[test]
 fn reset_and_abort_are_shutdown_acknowledgments() {
     for kind in [
diff --git a/src/cli/update/replace.rs b/src/cli/update/replace.rs
index 45b50421..4a3700c4 100644
--- a/src/cli/update/replace.rs
+++ b/src/cli/update/replace.rs
@@ -14,11 +14,6 @@ pub(super) fn replace_target(
             target.display()
         )
     })?;
-    if parked.is_some() {
-        println!(
-            "nightcrow: moved the installed binary aside — a running session keeps using it until it exits"
-        );
-    }
 
     match install(target).and_then(|()| {
         if target.is_file() {
@@ -47,18 +42,19 @@ pub(super) fn replace_target(
 }
 
 fn finish_success(parked: Option<&Path>) -> Result<()> {
-    if let Some(parked) = parked
-        && !self_replace::discard(parked)
-    {
-        println!(
-            "nightcrow: the previous binary is still in use and was left at {} — it is removed on a later start",
-            parked.display()
-        );
-    }
-    println!("nightcrow: updated — restart the session to run the new version");
+    let cleanup_pending = parked.is_some_and(|parked| !self_replace::discard(parked));
+    println!("{}", success_message(cleanup_pending));
     Ok(())
 }
 
+fn success_message(cleanup_pending: bool) -> &'static str {
+    if cleanup_pending {
+        "nightcrow: update installed successfully.\nnightcrow: the parked old binary is still in use by the running session or updater; cleanup is pending.\nnightcrow: no second update is needed. If a session is running, run `nightcrow stop`, then start nightcrow again to use the new version."
+    } else {
+        "nightcrow: update installed successfully.\nnightcrow: no second update is needed. If a session is running, run `nightcrow stop`, then start nightcrow again to use the new version."
+    }
+}
+
 fn rollback(target: &Path, parked: Option<&Path>) -> Result<()> {
     if target.exists() {
         std::fs::remove_file(target).with_context(|| {
diff --git a/src/cli/update/replace_tests.rs b/src/cli/update/replace_tests.rs
index 1ac9caee..e834ec46 100644
--- a/src/cli/update/replace_tests.rs
+++ b/src/cli/update/replace_tests.rs
@@ -30,3 +30,19 @@ fn a_successful_install_replaces_the_previous_binary() {
 
     assert_eq!(std::fs::read(&target).unwrap(), b"new");
 }
+
+#[test]
+fn successful_update_message_explains_pending_cleanup_without_a_path() {
+    assert_eq!(
+        success_message(true),
+        "nightcrow: update installed successfully.\nnightcrow: the parked old binary is still in use by the running session or updater; cleanup is pending.\nnightcrow: no second update is needed. If a session is running, run `nightcrow stop`, then start nightcrow again to use the new version."
+    );
+}
+
+#[test]
+fn successful_update_message_explains_restart_after_cleanup() {
+    assert_eq!(
+        success_message(false),
+        "nightcrow: update installed successfully.\nnightcrow: no second update is needed. If a session is running, run `nightcrow stop`, then start nightcrow again to use the new version."
+    );
+}
diff --git a/src/daemon/serve_tests/status.rs b/src/daemon/serve_tests/status.rs
index 09546fa1..c4954745 100644
--- a/src/daemon/serve_tests/status.rs
+++ b/src/daemon/serve_tests/status.rs
@@ -81,18 +81,21 @@ fn an_invalid_first_request_is_refused_without_attaching() {
 fn stop_request_is_still_accepted_before_attach() {
     let dir = tempfile::TempDir::new().unwrap();
     let daemon = daemon(&dir, &[]);
-
-    crate::cli::run_stop(Some(daemon.path().to_path_buf())).expect("stop request succeeds");
-
-    assert_eq!(
-        daemon
-            .shutdown_rx
-            .recv_timeout(std::time::Duration::from_millis(100))
-            .expect("the daemon receives the stop signal"),
-        crate::platform::signals::Shutdown::Terminate
-    );
+    let path = daemon.path().to_path_buf();
+    let stopping = std::thread::spawn(move || crate::cli::run_stop(Some(path)));
+
+    let signal = daemon
+        .shutdown_rx
+        .recv_timeout(std::time::Duration::from_millis(100))
+        .expect("the daemon receives the stop signal");
+    assert_eq!(signal, crate::platform::signals::Shutdown::Terminate);
     assert_eq!(daemon.session.clients.len(), 0);
     assert!(daemon.session.bridges.lock().unwrap().is_empty());
+    drop(daemon);
+    stopping
+        .join()
+        .expect("stop request thread does not panic")
+        .expect("stop request succeeds");
 }
 
 #[test]