diff --git a/TODO.md b/TODO.md
index d0b7920..852356e 100644
--- a/TODO.md
+++ b/TODO.md
@@ -27,6 +27,10 @@ real 5 GiB limit (https://git.eeqj.de/sneak/routewatch/issues/3).
 
 # Completed Steps
 
+- 2026-10-14: the daemon exits with status 1 when it cannot listen on its
+  port, for example because the port is in use, instead of running on without
+  its web server; any other error from `Run` also stops it with status 1
+  (closes #73)
 - 2026-10-03: `/api/v1/stats` serves the prefix distribution from memory,
   seeded at startup and adjusted on every live-route write, so a request no
   longer reads every live route (closes #30)
diff --git a/internal/routewatch/cli.go b/internal/routewatch/cli.go
index d857de7..6c2bd6c 100644
--- a/internal/routewatch/cli.go
+++ b/internal/routewatch/cli.go
@@ -20,6 +20,8 @@ const (
 	debugInterval = 60 * time.Second
 	// bytesPerMB is bytes per megabyte
 	bytesPerMB = 1024 * 1024
+	// failureExitCode is the exit status when RouteWatch stops on an error
+	failureExitCode = 1
 )
 
 // logDebugStats logs goroutine count and memory usage
@@ -83,6 +85,9 @@ func CLIEntry() {
 					go func() {
 						if err := rw.Run(ctx); err != nil {
 							logger.Error("RouteWatch error", "error", err)
+							if err := shutdowner.Shutdown(fx.ExitCode(failureExitCode)); err != nil {
+								logger.Error("Failed to shutdown gracefully", "error", err)
+							}
 						}
 					}()
 
diff --git a/internal/server/server.go b/internal/server/server.go
index 10f8649..16ba2b3 100644
--- a/internal/server/server.go
+++ b/internal/server/server.go
@@ -3,6 +3,8 @@ package server
 
 import (
 	"context"
+	"fmt"
+	"net"
 	"net/http"
 	"strconv"
 	"time"
@@ -53,9 +55,12 @@ func New(db database.Store, streamer *streamer.Streamer, logger *logger.Logger,
 	return s
 }
 
-// Start starts the HTTP server
+// Start listens on the configured port and serves HTTP in the background.
+// It returns an error if it cannot listen, for example because the port is
+// already in use.
 func (s *Server) Start() error {
 	const (
+		network           = "tcp"
 		readHeaderTimeout = 40 * time.Second
 		readTimeout       = 60 * time.Second
 		writeTimeout      = 60 * time.Second
@@ -73,10 +78,15 @@ func (s *Server) Start() error {
 
 	s.logger.Info("Starting HTTP server", "port", s.port, "addr", s.srv.Addr)
 
-	// Start in goroutine but log when actually listening
+	listener, err := net.Listen(network, s.srv.Addr)
+	if err != nil {
+		return fmt.Errorf("starting HTTP server: %w", err)
+	}
+
+	s.logger.Info("HTTP server listening", "addr", listener.Addr().String())
+
 	go func() {
-		s.logger.Info("HTTP server listening", "addr", s.srv.Addr)
-		if err := s.srv.ListenAndServe(); err != nil && err != http.ErrServerClosed {
+		if err := s.srv.Serve(listener); err != nil && err != http.ErrServerClosed {
 			s.logger.Error("HTTP server error", "error", err)
 		}
 	}()
diff --git a/internal/server/server_test.go b/internal/server/server_test.go
new file mode 100644
index 0000000..ff7c7d2
--- /dev/null
+++ b/internal/server/server_test.go
@@ -0,0 +1,33 @@
+package server
+
+import (
+	"context"
+	"net"
+	"testing"
+
+	"git.eeqj.de/sneak/routewatch/internal/config"
+	"git.eeqj.de/sneak/routewatch/internal/logger"
+	"git.eeqj.de/sneak/routewatch/internal/metrics"
+	"git.eeqj.de/sneak/routewatch/internal/streamer"
+)
+
+// TestStartFailsWhenPortIsHeld holds a port with a listener of its own and
+// checks that Start on that port returns an error. Before the fix Start
+// listened in a goroutine, only logged the failure and returned nil, so the
+// daemon kept running without its web server.
+func TestStartFailsWhenPortIsHeld(t *testing.T) {
+	held, err := net.Listen("tcp", ":0")
+	if err != nil {
+		t.Fatalf("failed to open the test listener: %v", err)
+	}
+	defer func() { _ = held.Close() }()
+
+	port := held.Addr().(*net.TCPAddr).Port
+	log := logger.New()
+	s := New(nil, streamer.New(log, metrics.New()), log, &config.Config{Port: port})
+	defer func() { _ = s.Stop(context.Background()) }()
+
+	if err := s.Start(); err == nil {
+		t.Fatalf("Start returned nil while port %d was held by another listener", port)
+	}
+}