diff --git a/cmd/inbucket/main.go b/cmd/inbucket/main.go
index 3b70cb3..834c05c 100644
--- a/cmd/inbucket/main.go
+++ b/cmd/inbucket/main.go
@@ -15,18 +15,10 @@ import (
 	"time"
 
 	"github.com/inbucket/inbucket/pkg/config"
-	"github.com/inbucket/inbucket/pkg/message"
-	"github.com/inbucket/inbucket/pkg/msghub"
-	"github.com/inbucket/inbucket/pkg/policy"
-	"github.com/inbucket/inbucket/pkg/rest"
-	"github.com/inbucket/inbucket/pkg/server/pop3"
-	"github.com/inbucket/inbucket/pkg/server/smtp"
-	"github.com/inbucket/inbucket/pkg/server/web"
+	"github.com/inbucket/inbucket/pkg/server"
 	"github.com/inbucket/inbucket/pkg/storage"
 	"github.com/inbucket/inbucket/pkg/storage/file"
 	"github.com/inbucket/inbucket/pkg/storage/mem"
-	"github.com/inbucket/inbucket/pkg/stringutil"
-	"github.com/inbucket/inbucket/pkg/webui"
 	"github.com/rs/zerolog"
 	"github.com/rs/zerolog/log"
 )
@@ -114,36 +106,16 @@ func main() {
 		}
 	}
 
-	// Configure internal services.
-	rootCtx, rootCancel := context.WithCancel(context.Background())
-	shutdownChan := make(chan bool)
-	store, err := storage.FromConfig(conf.Storage)
+	// Configure and start internal services.
+	svcCtx, svcCancel := context.WithCancel(context.Background())
+	services, err := server.FullAssembly(conf)
 	if err != nil {
+		startupLog.Fatal().Err(err).Msg("Fatal error during startup")
 		removePIDFile(*pidfile)
-		startupLog.Fatal().Err(err).Str("module", "storage").Msg("Fatal storage error")
 	}
-	msgHub := msghub.New(rootCtx, conf.Web.MonitorHistory)
-	addrPolicy := &policy.Addressing{Config: conf}
-	mmanager := &message.StoreManager{AddrPolicy: addrPolicy, Store: store, Hub: msgHub}
-
-	// Start Retention scanner.
-	retentionScanner := storage.NewRetentionScanner(conf.Storage, store, shutdownChan)
-	retentionScanner.Start()
-
-	// Configure routes and start HTTP server.
-	prefix := stringutil.MakePathPrefixer(conf.Web.BasePath)
-	webui.SetupRoutes(web.Router.PathPrefix(prefix("/serve/")).Subrouter())
-	rest.SetupRoutes(web.Router.PathPrefix(prefix("/api/")).Subrouter())
-	web.Initialize(conf, shutdownChan, mmanager, msgHub)
-	go web.Start(rootCtx)
-
-	// Start POP3 server.
-	pop3Server := pop3.New(conf.POP3, shutdownChan, store)
-	go pop3Server.Start(rootCtx)
-
-	// Start SMTP server.
-	smtpServer := smtp.NewServer(conf.SMTP, shutdownChan, mmanager, addrPolicy)
-	go smtpServer.Start(rootCtx)
+	services.Start(svcCtx, func() {
+		startupLog.Debug().Msg("All services report ready")
+	})
 
 	// Loop forever waiting for signals or shutdown channel.
 signalLoop:
@@ -155,24 +127,27 @@ signalLoop:
 				// Shutdown requested
 				log.Info().Str("phase", "shutdown").Str("signal", "SIGINT").
 					Msg("Received SIGINT, shutting down")
-				close(shutdownChan)
+				svcCancel()
+				break signalLoop
 			case syscall.SIGTERM:
 				// Shutdown requested
 				log.Info().Str("phase", "shutdown").Str("signal", "SIGTERM").
 					Msg("Received SIGTERM, shutting down")
-				close(shutdownChan)
+				svcCancel()
+				break signalLoop
 			}
-		case <-shutdownChan:
-			rootCancel()
+		case <-services.Notify():
+			log.Info().Str("phase", "shutdown").Msg("Shutting down due to service failure")
+			svcCancel()
 			break signalLoop
 		}
 	}
 
 	// Wait for active connections to finish.
 	go timedExit(*pidfile)
-	smtpServer.Drain()
-	pop3Server.Drain()
-	retentionScanner.Join()
+	services.SMTPServer.Drain()
+	services.POP3Server.Drain()
+	services.RetentionScanner.Join()
 	removePIDFile(*pidfile)
 	closeLog()
 }
diff --git a/pkg/msghub/hub.go b/pkg/msghub/hub.go
index 77e06ee..59f5445 100644
--- a/pkg/msghub/hub.go
+++ b/pkg/msghub/hub.go
@@ -36,27 +36,26 @@ type Hub struct {
 // New constructs a new Hub which will cache historyLen messages in memory for playback to future
 // listeners.  A goroutine is created to handle incoming messages; it will run until the provided
 // context is canceled.
-func New(ctx context.Context, historyLen int) *Hub {
-	h := &Hub{
+func New(historyLen int) *Hub {
+	return &Hub{
 		history:   ring.New(historyLen),
 		listeners: make(map[Listener]struct{}),
 		opChan:    make(chan func(h *Hub), opChanLen),
 	}
+}
 
-	go func() {
-		for {
-			select {
-			case <-ctx.Done():
-				// Shutdown
-				close(h.opChan)
-				return
-			case op := <-h.opChan:
-				op(h)
-			}
+// Start Hub processing loop.
+func (hub *Hub) Start(ctx context.Context) {
+	for {
+		select {
+		case <-ctx.Done():
+			// Shutdown
+			close(hub.opChan)
+			return
+		case op := <-hub.opChan:
+			op(hub)
 		}
-	}()
-
-	return h
+	}
 }
 
 // Dispatch queues a message for broadcast by the hub.  The message will be placed into the
diff --git a/pkg/msghub/hub_test.go b/pkg/msghub/hub_test.go
index db77c7f..5e0ec5c 100644
--- a/pkg/msghub/hub_test.go
+++ b/pkg/msghub/hub_test.go
@@ -52,9 +52,7 @@ func (l *testListener) String() string {
 }
 
 func TestHubNew(t *testing.T) {
-	ctx, cancel := context.WithCancel(context.Background())
-	defer cancel()
-	hub := New(ctx, 5)
+	hub := New(5)
 	if hub == nil {
 		t.Fatal("New() == nil, expected a new Hub")
 	}
@@ -63,29 +61,32 @@ func TestHubNew(t *testing.T) {
 func TestHubZeroLen(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 0)
+	hub := New(0)
+	go hub.Start(ctx)
 	m := Message{}
 	for i := 0; i < 100; i++ {
 		hub.Dispatch(m)
 	}
-	// Just making sure Hub doesn't panic
+	// Ensures Hub doesn't panic
 }
 
 func TestHubZeroListeners(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 5)
+	hub := New(5)
+	go hub.Start(ctx)
 	m := Message{}
 	for i := 0; i < 100; i++ {
 		hub.Dispatch(m)
 	}
-	// Just making sure Hub doesn't panic
+	// Ensures Hub doesn't panic
 }
 
 func TestHubOneListener(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 5)
+	hub := New(5)
+	go hub.Start(ctx)
 	m := Message{}
 	l := newTestListener(1)
 
@@ -103,7 +104,8 @@ func TestHubOneListener(t *testing.T) {
 func TestHubRemoveListener(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 5)
+	hub := New(5)
+	go hub.Start(ctx)
 	m := Message{}
 	l := newTestListener(1)
 
@@ -125,7 +127,8 @@ func TestHubRemoveListener(t *testing.T) {
 func TestHubRemoveListenerOnError(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 5)
+	hub := New(5)
+	go hub.Start(ctx)
 	m := Message{}
 
 	// error after 1 means listener should receive 2 messages before being removed
@@ -151,7 +154,8 @@ func TestHubRemoveListenerOnError(t *testing.T) {
 func TestHubHistoryReplay(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 100)
+	hub := New(100)
+	go hub.Start(ctx)
 	l1 := newTestListener(3)
 	hub.AddListener(l1)
 
@@ -194,7 +198,8 @@ func TestHubHistoryReplay(t *testing.T) {
 func TestHubHistoryReplayWrap(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
-	hub := New(ctx, 5)
+	hub := New(5)
+	go hub.Start(ctx)
 	l1 := newTestListener(20)
 	hub.AddListener(l1)
 
@@ -236,7 +241,8 @@ func TestHubHistoryReplayWrap(t *testing.T) {
 
 func TestHubContextCancel(t *testing.T) {
 	ctx, cancel := context.WithCancel(context.Background())
-	hub := New(ctx, 5)
+	hub := New(5)
+	go hub.Start(ctx)
 	m := Message{}
 	l := newTestListener(1)
 
diff --git a/pkg/rest/testutils_test.go b/pkg/rest/testutils_test.go
index 9936b52..a64f411 100644
--- a/pkg/rest/testutils_test.go
+++ b/pkg/rest/testutils_test.go
@@ -48,9 +48,8 @@ func setupWebServer(mm message.Manager) *bytes.Buffer {
 			UIDir: "../ui",
 		},
 	}
-	shutdownChan := make(chan bool)
 	SetupRoutes(web.Router.PathPrefix("/api/").Subrouter())
-	web.Initialize(cfg, shutdownChan, mm, &msghub.Hub{})
+	web.NewServer(cfg, mm, &msghub.Hub{})
 
 	return buf
 }
diff --git a/pkg/server/lifecycle.go b/pkg/server/lifecycle.go
new file mode 100644
index 0000000..79b477d
--- /dev/null
+++ b/pkg/server/lifecycle.go
@@ -0,0 +1,105 @@
+package server
+
+import (
+	"context"
+	"sync"
+
+	"github.com/inbucket/inbucket/pkg/config"
+	"github.com/inbucket/inbucket/pkg/message"
+	"github.com/inbucket/inbucket/pkg/msghub"
+	"github.com/inbucket/inbucket/pkg/policy"
+	"github.com/inbucket/inbucket/pkg/rest"
+	"github.com/inbucket/inbucket/pkg/server/pop3"
+	"github.com/inbucket/inbucket/pkg/server/smtp"
+	"github.com/inbucket/inbucket/pkg/server/web"
+	"github.com/inbucket/inbucket/pkg/storage"
+	"github.com/inbucket/inbucket/pkg/stringutil"
+	"github.com/inbucket/inbucket/pkg/webui"
+)
+
+// Services holds the configured services.
+type Services struct {
+	MsgHub           *msghub.Hub
+	POP3Server       *pop3.Server
+	RetentionScanner *storage.RetentionScanner
+	SMTPServer       *smtp.Server
+	WebServer        *web.Server
+	notify           chan error      // Combined notification for failed services.
+	ready            *sync.WaitGroup // Tracks services that have not reported ready.
+}
+
+// FullAssembly wires up a complete Inbucket environment.
+func FullAssembly(conf *config.Root) (*Services, error) {
+	// Configure storage.
+	store, err := storage.FromConfig(conf.Storage)
+	if err != nil {
+		return nil, err
+	}
+
+	addrPolicy := &policy.Addressing{Config: conf}
+	msgHub := msghub.New(conf.Web.MonitorHistory)
+	mmanager := &message.StoreManager{AddrPolicy: addrPolicy, Store: store, Hub: msgHub}
+
+	// Start Retention scanner.
+	retentionScanner := storage.NewRetentionScanner(conf.Storage, store)
+
+	// Configure routes and build HTTP server.
+	prefix := stringutil.MakePathPrefixer(conf.Web.BasePath)
+	webui.SetupRoutes(web.Router.PathPrefix(prefix("/serve/")).Subrouter())
+	rest.SetupRoutes(web.Router.PathPrefix(prefix("/api/")).Subrouter())
+	webServer := web.NewServer(conf, mmanager, msgHub)
+
+	pop3Server := pop3.NewServer(conf.POP3, store)
+	smtpServer := smtp.NewServer(conf.SMTP, mmanager, addrPolicy)
+
+	return &Services{
+		MsgHub:           msgHub,
+		RetentionScanner: retentionScanner,
+		POP3Server:       pop3Server,
+		SMTPServer:       smtpServer,
+		WebServer:        webServer,
+		ready:            &sync.WaitGroup{},
+	}, nil
+}
+
+// Start all services, returns immediately.  Callers may use Notify to detect failed services.
+func (s *Services) Start(ctx context.Context, readyFunc func()) {
+	go s.MsgHub.Start(ctx)
+	go s.WebServer.Start(ctx, s.makeReadyFunc())
+	go s.SMTPServer.Start(ctx, s.makeReadyFunc())
+	go s.POP3Server.Start(ctx, s.makeReadyFunc())
+	go s.RetentionScanner.Start(ctx)
+
+	// Notify when all services report ready.
+	go func() {
+		s.ready.Wait()
+		readyFunc()
+	}()
+}
+
+// Notify merges the error notification channels of all fallible services, allowing the process to
+// be shutdown if needed.
+func (s *Services) Notify() <-chan error {
+	c := make(chan error, 1)
+	go func() {
+		// TODO: What level to log failure.
+		select {
+		case err := <-s.POP3Server.Notify():
+			c <- err
+		case err := <-s.SMTPServer.Notify():
+			c <- err
+		case err := <-s.WebServer.Notify():
+			c <- err
+		}
+	}()
+
+	return c
+}
+
+func (s *Services) makeReadyFunc() func() {
+	s.ready.Add(1)
+	var once sync.Once
+	return func() {
+		once.Do(s.ready.Done)
+	}
+}
diff --git a/pkg/server/pop3/listener.go b/pkg/server/pop3/listener.go
index b1aa002..8216593 100644
--- a/pkg/server/pop3/listener.go
+++ b/pkg/server/pop3/listener.go
@@ -13,47 +13,53 @@ import (
 
 // Server defines an instance of the POP3 server.
 type Server struct {
-	config         config.POP3     // POP3 configuration.
-	store          storage.Store   // Mail store.
-	listener       net.Listener    // TCP listener.
-	globalShutdown chan bool       // Inbucket shutdown signal.
-	wg             *sync.WaitGroup // Waitgroup tracking sessions.
+	config   config.POP3     // POP3 configuration.
+	store    storage.Store   // Mail store.
+	listener net.Listener    // TCP listener.
+	wg       *sync.WaitGroup // Waitgroup tracking sessions.
+	notify   chan error      // Notify on fatal error.
 }
 
-// New creates a new Server struct.
-func New(pop3Config config.POP3, shutdownChan chan bool, store storage.Store) *Server {
+// NewServer creates a new, unstarted, POP3 server.
+func NewServer(pop3Config config.POP3, store storage.Store) *Server {
 	return &Server{
-		config:         pop3Config,
-		store:          store,
-		globalShutdown: shutdownChan,
-		wg:             new(sync.WaitGroup),
+		config: pop3Config,
+		store:  store,
+		wg:     new(sync.WaitGroup),
+		notify: make(chan error, 1),
 	}
 }
 
 // Start the server and listen for connections
-func (s *Server) Start(ctx context.Context) {
+func (s *Server) Start(ctx context.Context, readyFunc func()) {
 	slog := log.With().Str("module", "pop3").Str("phase", "startup").Logger()
 	addr, err := net.ResolveTCPAddr("tcp4", s.config.Addr)
 	if err != nil {
 		slog.Error().Err(err).Msg("Failed to build tcp4 address")
-		s.emergencyShutdown()
+		s.notify <- err
+		close(s.notify)
 		return
 	}
 	slog.Info().Str("addr", addr.String()).Msg("POP3 listening on tcp4")
 	s.listener, err = net.ListenTCP("tcp4", addr)
 	if err != nil {
 		slog.Error().Err(err).Msg("Failed to start tcp4 listener")
-		s.emergencyShutdown()
+		s.notify <- err
+		close(s.notify)
 		return
 	}
-	// Listener go routine.
+
+	// Start listener go routine.
 	go s.serve(ctx)
+	readyFunc()
+
 	// Wait for shutdown.
 	select {
 	case _ = <-ctx.Done():
 	}
 	slog = log.With().Str("module", "pop3").Str("phase", "shutdown").Logger()
 	slog.Debug().Msg("POP3 shutdown requested, connections will be drained")
+
 	// Closing the listener will cause the serve() go routine to exit.
 	if err := s.listener.Close(); err != nil {
 		slog.Error().Err(err).Msg("Failed to close POP3 listener")
@@ -88,7 +94,8 @@ func (s *Server) serve(ctx context.Context) {
 					return
 				default:
 					// Something went wrong.
-					s.emergencyShutdown()
+					s.notify <- err
+					close(s.notify)
 					return
 				}
 			}
@@ -100,18 +107,14 @@ func (s *Server) serve(ctx context.Context) {
 	}
 }
 
-func (s *Server) emergencyShutdown() {
-	// Shutdown Inbucket
-	select {
-	case _ = <-s.globalShutdown:
-	default:
-		close(s.globalShutdown)
-	}
-}
-
 // Drain causes the caller to block until all active POP3 sessions have finished
 func (s *Server) Drain() {
 	// Wait for sessions to close
 	s.wg.Wait()
 	log.Debug().Str("module", "pop3").Str("phase", "shutdown").Msg("POP3 connections have drained")
 }
+
+// Notify allows the running POP3 server to be monitored for a fatal error.
+func (s *Server) Notify() <-chan error {
+	return s.notify
+}
diff --git a/pkg/server/smtp/handler_test.go b/pkg/server/smtp/handler_test.go
index 6cf2cb6..f07e824 100644
--- a/pkg/server/smtp/handler_test.go
+++ b/pkg/server/smtp/handler_test.go
@@ -484,13 +484,11 @@ func setupSMTPServer(ds storage.Store) (s *Server, buf *bytes.Buffer, teardown f
 	buf = new(bytes.Buffer)
 	log.SetOutput(buf)
 	// Create a server, don't start it.
-	shutdownChan := make(chan bool)
-	teardown = func() {
-		close(shutdownChan)
-	}
+	// TODO Remove teardown.
+	teardown = func() {}
 	addrPolicy := &policy.Addressing{Config: cfg}
 	manager := &message.StoreManager{Store: ds}
-	s = NewServer(cfg.SMTP, shutdownChan, manager, addrPolicy)
+	s = NewServer(cfg.SMTP, manager, addrPolicy)
 	return s, buf, teardown
 }
 
diff --git a/pkg/server/smtp/listener.go b/pkg/server/smtp/listener.go
index 9ef8c4e..5a281f7 100644
--- a/pkg/server/smtp/listener.go
+++ b/pkg/server/smtp/listener.go
@@ -58,19 +58,18 @@ func init() {
 
 // Server holds the configuration and state of our SMTP server.
 type Server struct {
-	config         config.SMTP        // SMTP configuration.
-	addrPolicy     *policy.Addressing // Address policy.
-	globalShutdown chan bool          // Shuts down Inbucket.
-	manager        message.Manager    // Used to deliver messages.
-	listener       net.Listener       // Incoming network connections.
-	wg             *sync.WaitGroup    // Waitgroup tracks individual sessions.
-	tlsConfig      *tls.Config
+	config     config.SMTP        // SMTP configuration.
+	addrPolicy *policy.Addressing // Address policy.
+	manager    message.Manager    // Used to deliver messages.
+	listener   net.Listener       // Incoming network connections.
+	wg         *sync.WaitGroup    // Waitgroup tracks individual sessions.
+	tlsConfig  *tls.Config        // TLS encryption configuration.
+	notify     chan error         // Notify on fatal error.
 }
 
-// NewServer creates a new Server instance with the specificed config.
+// NewServer creates a new, unstarted, SMTP server instance with the specificed config.
 func NewServer(
 	smtpConfig config.SMTP,
-	globalShutdown chan bool,
 	manager message.Manager,
 	apolicy *policy.Addressing,
 ) *Server {
@@ -90,37 +89,43 @@ func NewServer(
 	}
 
 	return &Server{
-		config:         smtpConfig,
-		globalShutdown: globalShutdown,
-		manager:        manager,
-		addrPolicy:     apolicy,
-		wg:             new(sync.WaitGroup),
-		tlsConfig:      tlsConfig,
+		config:     smtpConfig,
+		manager:    manager,
+		addrPolicy: apolicy,
+		wg:         new(sync.WaitGroup),
+		tlsConfig:  tlsConfig,
+		notify:     make(chan error, 1),
 	}
 }
 
 // Start the listener and handle incoming connections.
-func (s *Server) Start(ctx context.Context) {
+func (s *Server) Start(ctx context.Context, readyFunc func()) {
 	slog := log.With().Str("module", "smtp").Str("phase", "startup").Logger()
 	addr, err := net.ResolveTCPAddr("tcp4", s.config.Addr)
 	if err != nil {
 		slog.Error().Err(err).Msg("Failed to build tcp4 address")
-		s.emergencyShutdown()
+		s.notify <- err
+		close(s.notify)
 		return
 	}
 	slog.Info().Str("addr", addr.String()).Msg("SMTP listening on tcp4")
 	s.listener, err = net.ListenTCP("tcp4", addr)
 	if err != nil {
 		slog.Error().Err(err).Msg("Failed to start tcp4 listener")
-		s.emergencyShutdown()
+		s.notify <- err
+		close(s.notify)
 		return
 	}
-	// Listener go routine.
+
+	// Start listener go routine.
 	go s.serve(ctx)
+	readyFunc()
+
 	// Wait for shutdown.
 	<-ctx.Done()
 	slog = log.With().Str("module", "smtp").Str("phase", "shutdown").Logger()
 	slog.Debug().Msg("SMTP shutdown requested, connections will be drained")
+
 	// Closing the listener will cause the serve() go routine to exit.
 	if err := s.listener.Close(); err != nil {
 		slog.Error().Err(err).Msg("Failed to close SMTP listener")
@@ -156,7 +161,8 @@ func (s *Server) serve(ctx context.Context) {
 					return
 				default:
 					// Something went wrong.
-					s.emergencyShutdown()
+					s.notify <- err
+					close(s.notify)
 					return
 				}
 			}
@@ -169,18 +175,14 @@ func (s *Server) serve(ctx context.Context) {
 	}
 }
 
-func (s *Server) emergencyShutdown() {
-	// Shutdown Inbucket.
-	select {
-	case <-s.globalShutdown:
-	default:
-		close(s.globalShutdown)
-	}
-}
-
 // Drain causes the caller to block until all active SMTP sessions have finished
 func (s *Server) Drain() {
 	// Wait for sessions to close.
 	s.wg.Wait()
 	log.Debug().Str("module", "smtp").Str("phase", "shutdown").Msg("SMTP connections have drained")
 }
+
+// Notify allows the running SMTP server to be monitored for a fatal error.
+func (s *Server) Notify() <-chan error {
+	return s.notify
+}
diff --git a/pkg/server/web/server.go b/pkg/server/web/server.go
index b4ce078..9e0e4f4 100644
--- a/pkg/server/web/server.go
+++ b/pkg/server/web/server.go
@@ -31,10 +31,9 @@ var (
 	// incoming requests to the correct handler function
 	Router = mux.NewRouter()
 
-	rootConfig     *config.Root
-	server         *http.Server
-	listener       net.Listener
-	globalShutdown chan bool
+	rootConfig *config.Root
+	server     *http.Server
+	listener   net.Listener
 
 	// ExpWebSocketConnectsCurrent tracks the number of open WebSockets
 	ExpWebSocketConnectsCurrent = new(expvar.Int)
@@ -45,15 +44,19 @@ func init() {
 	m.Set("WebSocketConnectsCurrent", ExpWebSocketConnectsCurrent)
 }
 
-// Initialize sets up things for unit tests or the Start() method.
-func Initialize(
+// Server defines an instance of the Web server.
+type Server struct {
+	// TODO Migrate global vars here.
+	notify chan error // Notify on fatal error.
+}
+
+// NewServer sets up things for unit tests or the Start() method.
+func NewServer(
 	conf *config.Root,
-	shutdownChan chan bool,
 	mm message.Manager,
-	mh *msghub.Hub) {
+	mh *msghub.Hub) *Server {
 
 	rootConfig = conf
-	globalShutdown = shutdownChan
 
 	// NewContext() will use this DataStore for the web handlers.
 	msgHub = mh
@@ -118,10 +121,16 @@ func Initialize(
 		http.StatusNotFound, "No route matches URI path")
 	Router.MethodNotAllowedHandler = noMatchHandler(
 		http.StatusMethodNotAllowed, "Method not allowed for URI path")
+
+	s := &Server{
+		notify: make(chan error, 1),
+	}
+
+	return s
 }
 
 // Start begins listening for HTTP requests
-func Start(ctx context.Context) {
+func (s *Server) Start(ctx context.Context, readyFunc func()) {
 	server = &http.Server{
 		Addr:         rootConfig.Web.Addr,
 		Handler:      requestLoggingWrapper(Router),
@@ -137,12 +146,14 @@ func Start(ctx context.Context) {
 	if err != nil {
 		log.Error().Str("module", "web").Str("phase", "startup").Err(err).
 			Msg("HTTP failed to start TCP4 listener")
-		emergencyShutdown()
+		s.notify <- err
+		close(s.notify)
 		return
 	}
 
-	// Listener go routine
-	go serve(ctx)
+	// Start listener go routine
+	go s.serve(ctx)
+	readyFunc()
 
 	// Wait for shutdown
 	select {
@@ -176,7 +187,7 @@ func appConfigCookie(webConfig config.Web) *http.Cookie {
 }
 
 // serve begins serving HTTP requests
-func serve(ctx context.Context) {
+func (s *Server) serve(ctx context.Context) {
 	// server.Serve blocks until we close the listener
 	err := server.Serve(listener)
 
@@ -186,16 +197,13 @@ func serve(ctx context.Context) {
 	default:
 		log.Error().Str("module", "web").Str("phase", "startup").Err(err).
 			Msg("HTTP server failed")
-		emergencyShutdown()
+		s.notify <- err
+		close(s.notify)
 		return
 	}
 }
 
-func emergencyShutdown() {
-	// Shutdown Inbucket
-	select {
-	case _ = <-globalShutdown:
-	default:
-		close(globalShutdown)
-	}
+// Notify allows the running Web server to be monitored for a fatal error.
+func (s *Server) Notify() <-chan error {
+	return s.notify
 }
diff --git a/pkg/storage/retention.go b/pkg/storage/retention.go
index 86839c1..70ed315 100644
--- a/pkg/storage/retention.go
+++ b/pkg/storage/retention.go
@@ -2,6 +2,7 @@ package storage
 
 import (
 	"container/list"
+	"context"
 	"expvar"
 	"time"
 
@@ -50,7 +51,6 @@ func init() {
 
 // RetentionScanner looks for messages older than the configured retention period and deletes them.
 type RetentionScanner struct {
-	globalShutdown    chan bool // Closes when Inbucket needs to shut down
 	retentionShutdown chan bool // Closed after the scanner has shut down
 	ds                Store
 	retentionPeriod   time.Duration
@@ -61,10 +61,8 @@ type RetentionScanner struct {
 func NewRetentionScanner(
 	cfg config.Storage,
 	ds Store,
-	shutdownChannel chan bool,
 ) *RetentionScanner {
 	rs := &RetentionScanner{
-		globalShutdown:    shutdownChannel,
 		retentionShutdown: make(chan bool),
 		ds:                ds,
 		retentionPeriod:   cfg.RetentionPeriod,
@@ -76,20 +74,16 @@ func NewRetentionScanner(
 }
 
 // Start up the retention scanner if retention period > 0
-func (rs *RetentionScanner) Start() {
+func (rs *RetentionScanner) Start(ctx context.Context) {
+	slog := log.With().Str("module", "storage").Logger()
+
 	if rs.retentionPeriod <= 0 {
-		log.Info().Str("phase", "startup").Str("module", "storage").Msg("Retention scanner disabled")
+		slog.Info().Str("phase", "startup").Msg("Retention scanner disabled")
 		close(rs.retentionShutdown)
 		return
 	}
-	log.Info().Str("phase", "startup").Str("module", "storage").
-		Msgf("Retention configured for %v", rs.retentionPeriod)
-	go rs.run()
-}
+	slog.Info().Str("phase", "startup").Msgf("Retention configured for %v", rs.retentionPeriod)
 
-// run loops to kick off the scanner on the correct schedule
-func (rs *RetentionScanner) run() {
-	slog := log.With().Str("module", "storage").Logger()
 	start := time.Now()
 retentionLoop:
 	for {
@@ -99,19 +93,19 @@ retentionLoop:
 			dur := time.Minute - since
 			slog.Debug().Msgf("Retention scanner sleeping for %v", dur)
 			select {
-			case <-rs.globalShutdown:
+			case <-ctx.Done():
 				break retentionLoop
 			case <-time.After(dur):
 			}
 		}
 		// Kickoff scan
 		start = time.Now()
-		if err := rs.DoScan(); err != nil {
+		if err := rs.DoScan(ctx); err != nil {
 			slog.Error().Err(err).Msg("Error during retention scan")
 		}
 		// Check for global shutdown
 		select {
-		case <-rs.globalShutdown:
+		case <-ctx.Done():
 			break retentionLoop
 		default:
 		}
@@ -121,13 +115,14 @@ retentionLoop:
 }
 
 // DoScan does a single pass of all mailboxes looking for messages that can be purged.
-func (rs *RetentionScanner) DoScan() error {
+func (rs *RetentionScanner) DoScan(ctx context.Context) error {
 	slog := log.With().Str("module", "storage").Logger()
 	slog.Debug().Msg("Starting retention scan")
 	cutoff := time.Now().Add(-1 * rs.retentionPeriod)
+
+	// Loop over all mailboxes.
 	retained := 0
 	storeSize := int64(0)
-	// Loop over all mailboxes.
 	err := rs.ds.VisitMailboxes(func(messages []Message) bool {
 		for _, msg := range messages {
 			if msg.Date().Before(cutoff) {
@@ -145,7 +140,7 @@ func (rs *RetentionScanner) DoScan() error {
 			}
 		}
 		select {
-		case <-rs.globalShutdown:
+		case <-ctx.Done():
 			slog.Debug().Str("phase", "shutdown").Msg("Retention scan aborted due to shutdown")
 			return false
 		case <-time.After(rs.retentionSleep):
@@ -156,10 +151,12 @@ func (rs *RetentionScanner) DoScan() error {
 	if err != nil {
 		return err
 	}
+
 	// Update metrics
 	scanCompletedMillis.Set(time.Now().UnixNano() / 1000000)
 	expRetainedCurrent.Set(int64(retained))
 	expRetainedSize.Set(storeSize)
+
 	return nil
 }
 
diff --git a/pkg/storage/retention_test.go b/pkg/storage/retention_test.go
index 52c9934..b9a6e57 100644
--- a/pkg/storage/retention_test.go
+++ b/pkg/storage/retention_test.go
@@ -1,6 +1,7 @@
 package storage_test
 
 import (
+	"context"
 	"fmt"
 	"testing"
 	"time"
@@ -13,6 +14,7 @@ import (
 
 func TestDoRetentionScan(t *testing.T) {
 	ds := test.NewStore()
+
 	// Mockup some different aged messages (num is in hours)
 	new1 := stubMessage("mb1", 0)
 	new2 := stubMessage("mb2", 1)
@@ -26,22 +28,26 @@ func TestDoRetentionScan(t *testing.T) {
 	ds.AddMessage(old3)
 	ds.AddMessage(new2)
 	ds.AddMessage(new3)
+
 	// Test 4 hour retention
 	cfg := config.Storage{
 		RetentionPeriod: 239 * time.Minute,
 		RetentionSleep:  0,
 	}
-	shutdownChan := make(chan bool)
-	rs := storage.NewRetentionScanner(cfg, ds, shutdownChan)
-	if err := rs.DoScan(); err != nil {
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+	rs := storage.NewRetentionScanner(cfg, ds)
+	if err := rs.DoScan(ctx); err != nil {
 		t.Error(err)
 	}
+
 	// Delete should not have been called on new messages
 	for _, m := range []storage.Message{new1, new2, new3} {
 		if ds.MessageDeleted(m) {
 			t.Errorf("Expected %v to be present, was deleted", m.ID())
 		}
 	}
+
 	// Delete should have been called once on old messages
 	for _, m := range []storage.Message{old1, old2, old3} {
 		if !ds.MessageDeleted(m) {
diff --git a/pkg/test/integration_test.go b/pkg/test/integration_test.go
index 704e493..14cf476 100644
--- a/pkg/test/integration_test.go
+++ b/pkg/test/integration_test.go
@@ -214,7 +214,7 @@ func formatMessage(m *client.Message) []byte {
 }
 
 func startServer() (func(), error) {
-	// TODO Refactor inbucket/main.go so we don't need to repeat all this here.
+	// TODO Move integration setup into lifecycle.
 	log.Logger = log.Output(zerolog.ConsoleWriter{Out: os.Stderr, NoColor: true})
 	storage.Constructors["memory"] = mem.New
 	os.Clearenv()
@@ -222,32 +222,34 @@ func startServer() (func(), error) {
 	if err != nil {
 		return nil, err
 	}
-	rootCtx, rootCancel := context.WithCancel(context.Background())
-	shutdownChan := make(chan bool)
+	svcCtx, svcCancel := context.WithCancel(context.Background())
 	store, err := storage.FromConfig(conf.Storage)
 	if err != nil {
-		rootCancel()
+		svcCancel()
 		return nil, err
 	}
-	msgHub := msghub.New(rootCtx, conf.Web.MonitorHistory)
+
+	// TODO Test should not pass with unstarted msghub.
+	msgHub := msghub.New(conf.Web.MonitorHistory)
 	addrPolicy := &policy.Addressing{Config: conf}
 	mmanager := &message.StoreManager{AddrPolicy: addrPolicy, Store: store, Hub: msgHub}
+
 	// Start HTTP server.
 	webui.SetupRoutes(web.Router.PathPrefix("/serve/").Subrouter())
 	rest.SetupRoutes(web.Router.PathPrefix("/api/").Subrouter())
-	web.Initialize(conf, shutdownChan, mmanager, msgHub)
-	go web.Start(rootCtx)
-	// Start SMTP server.
-	smtpServer := smtp.NewServer(conf.SMTP, shutdownChan, mmanager, addrPolicy)
-	go smtpServer.Start(rootCtx)
+	webServer := web.NewServer(conf, mmanager, msgHub)
+	go webServer.Start(svcCtx, func() {})
 
-	// TODO Implmement an elegant way to determine server readiness.
+	// Start SMTP server.
+	smtpServer := smtp.NewServer(conf.SMTP, mmanager, addrPolicy)
+	go smtpServer.Start(svcCtx, func() {})
+
+	// TODO Use a readyFunc to determine server readiness.
 	time.Sleep(500 * time.Millisecond)
 
 	return func() {
 		// Shut everything down.
-		close(shutdownChan)
-		rootCancel()
+		svcCancel()
 		smtpServer.Drain()
 	}, nil
 }