diff --git a/cmd/dendrite-demo-pinecone/monolith/monolith.go b/cmd/dendrite-demo-pinecone/monolith/monolith.go
index 27720369e..e8a29e418 100644
--- a/cmd/dendrite-demo-pinecone/monolith/monolith.go
+++ b/cmd/dendrite-demo-pinecone/monolith/monolith.go
@@ -68,12 +68,14 @@ type P2PMonolith struct {
 	EventChannel   chan pineconeEvents.Event
 	RelayRetriever relay.RelayServerRetriever
 
-	dendrite       setup.Monolith
-	port           int
-	httpMux        *mux.Router
-	pineconeMux    *mux.Router
-	listener       net.Listener
-	httpListenAddr string
+	dendrite           setup.Monolith
+	port               int
+	httpMux            *mux.Router
+	pineconeMux        *mux.Router
+	httpServer         *http.Server
+	listener           net.Listener
+	httpListenAddr     string
+	stopHandlingEvents chan bool
 }
 
 func GenerateDefaultConfig(sk ed25519.PrivateKey, storageDir string, cacheDir string, dbPrefix string) *config.Dendrite {
@@ -199,8 +201,10 @@ func (p *P2PMonolith) StartMonolith() {
 }
 
 func (p *P2PMonolith) Stop() {
+	logrus.Info("Stopping monolith")
 	_ = p.BaseDendrite.Close()
 	p.WaitForShutdown()
+	logrus.Info("Stopped monolith")
 }
 
 func (p *P2PMonolith) WaitForShutdown() {
@@ -209,6 +213,16 @@ func (p *P2PMonolith) WaitForShutdown() {
 }
 
 func (p *P2PMonolith) closeAllResources() {
+	logrus.Info("Closing monolith resources")
+	if p.httpServer != nil {
+		p.httpServer.Shutdown(context.Background())
+	}
+
+	select {
+	case p.stopHandlingEvents <- true:
+	default:
+	}
+
 	if p.listener != nil {
 		_ = p.listener.Close()
 	}
@@ -224,6 +238,7 @@ func (p *P2PMonolith) closeAllResources() {
 	if p.Router != nil {
 		_ = p.Router.Close()
 	}
+	logrus.Info("Monolith resources closed")
 }
 
 func (p *P2PMonolith) Addr() string {
@@ -280,7 +295,7 @@ func (p *P2PMonolith) setupHttpServers(userProvider *users.PineconeUserProvider,
 func (p *P2PMonolith) startHTTPServers() {
 	go func() {
 		// Build both ends of a HTTP multiplex.
-		httpServer := &http.Server{
+		p.httpServer = &http.Server{
 			Addr:         ":0",
 			TLSNextProto: map[string]func(*http.Server, *tls.Conn, http.Handler){},
 			ReadTimeout:  10 * time.Second,
@@ -296,12 +311,13 @@ func (p *P2PMonolith) startHTTPServers() {
 		pubkeyString := hex.EncodeToString(pubkey[:])
 		logrus.Info("Listening on ", pubkeyString)
 
-		switch httpServer.Serve(p.Sessions.Protocol(SessionProtocol)) {
+		switch p.httpServer.Serve(p.Sessions.Protocol(SessionProtocol)) {
 		case net.ErrClosed, http.ErrServerClosed:
 			logrus.Info("Stopped listening on ", pubkeyString)
 		default:
 			logrus.Error("Stopped listening on ", pubkeyString)
 		}
+		logrus.Info("Stopped goroutine listening on ", pubkeyString)
 	}()
 
 	p.httpListenAddr = fmt.Sprintf(":%d", p.port)
@@ -313,10 +329,12 @@ func (p *P2PMonolith) startHTTPServers() {
 		default:
 			logrus.Error("Stopped listening on ", p.httpListenAddr)
 		}
+		logrus.Info("Stopped goroutine listening on ", p.httpListenAddr)
 	}()
 }
 
 func (p *P2PMonolith) startEventHandler() {
+	p.stopHandlingEvents = make(chan bool)
 	stopRelayServerSync := make(chan bool)
 	eLog := logrus.WithField("pinecone", "events")
 	p.RelayRetriever = relay.NewRelayServerRetriever(
@@ -329,25 +347,40 @@ func (p *P2PMonolith) startEventHandler() {
 	p.RelayRetriever.InitializeRelayServers(eLog)
 
 	go func(ch <-chan pineconeEvents.Event) {
-		for event := range ch {
-			switch e := event.(type) {
-			case pineconeEvents.PeerAdded:
-				p.RelayRetriever.StartSync()
-			case pineconeEvents.PeerRemoved:
-				if p.RelayRetriever.IsRunning() && p.Router.TotalPeerCount() == 0 {
-					stopRelayServerSync <- true
-				}
-			case pineconeEvents.BroadcastReceived:
-				// eLog.Info("Broadcast received from: ", e.PeerID)
+		for {
+			select {
+			case event := <-ch:
+				switch e := event.(type) {
+				case pineconeEvents.PeerAdded:
+					p.RelayRetriever.StartSync()
+				case pineconeEvents.PeerRemoved:
+					if p.RelayRetriever.IsRunning() && p.Router.TotalPeerCount() == 0 {
+						// NOTE: Don't block on channel
+						select {
+						case stopRelayServerSync <- true:
+						default:
+						}
+					}
+				case pineconeEvents.BroadcastReceived:
+					// eLog.Info("Broadcast received from: ", e.PeerID)
 
-				req := &federationAPI.PerformWakeupServersRequest{
-					ServerNames: []gomatrixserverlib.ServerName{gomatrixserverlib.ServerName(e.PeerID)},
+					req := &federationAPI.PerformWakeupServersRequest{
+						ServerNames: []gomatrixserverlib.ServerName{gomatrixserverlib.ServerName(e.PeerID)},
+					}
+					res := &federationAPI.PerformWakeupServersResponse{}
+					if err := p.dendrite.FederationAPI.PerformWakeupServers(p.BaseDendrite.Context(), req, res); err != nil {
+						eLog.WithError(err).Error("Failed to wakeup destination", e.PeerID)
+					}
 				}
-				res := &federationAPI.PerformWakeupServersResponse{}
-				if err := p.dendrite.FederationAPI.PerformWakeupServers(p.BaseDendrite.Context(), req, res); err != nil {
-					eLog.WithError(err).Error("Failed to wakeup destination", e.PeerID)
+			case <-p.stopHandlingEvents:
+				logrus.Info("Stopping processing pinecone events")
+				// NOTE: Don't block on channel
+				select {
+				case stopRelayServerSync <- true:
+				default:
 				}
-			default:
+				logrus.Info("Stopped processing pinecone events")
+				return
 			}
 		}
 	}(p.EventChannel)
diff --git a/cmd/dendrite-demo-pinecone/relay/retriever.go b/cmd/dendrite-demo-pinecone/relay/retriever.go
index 1b5c617ef..6b34f6416 100644
--- a/cmd/dendrite-demo-pinecone/relay/retriever.go
+++ b/cmd/dendrite-demo-pinecone/relay/retriever.go
@@ -38,7 +38,7 @@ type RelayServerRetriever struct {
 	relayServersQueried map[gomatrixserverlib.ServerName]bool
 	queriedServersMutex sync.Mutex
 	running             atomic.Bool
-	quit                <-chan bool
+	quit                chan bool
 }
 
 func NewRelayServerRetriever(
@@ -46,7 +46,7 @@ func NewRelayServerRetriever(
 	serverName gomatrixserverlib.ServerName,
 	federationAPI federationAPI.FederationInternalAPI,
 	relayAPI relayServerAPI.RelayInternalAPI,
-	quit <-chan bool,
+	quit chan bool,
 ) RelayServerRetriever {
 	return RelayServerRetriever{
 		ctx:                 ctx,
@@ -151,6 +151,7 @@ func (r *RelayServerRetriever) SyncRelayServers(stop <-chan bool) {
 			if !t.Stop() {
 				<-t.C
 			}
+			logrus.Info("Stopped relay server retriever")
 			return
 		case <-t.C:
 		}
diff --git a/cmd/dendrite-demo-pinecone/relay/retriever_test.go b/cmd/dendrite-demo-pinecone/relay/retriever_test.go
index 8f86a3770..6c4c3a529 100644
--- a/cmd/dendrite-demo-pinecone/relay/retriever_test.go
+++ b/cmd/dendrite-demo-pinecone/relay/retriever_test.go
@@ -60,7 +60,7 @@ func TestRelayRetrieverInitialization(t *testing.T) {
 		"server",
 		&FakeFedAPI{},
 		&FakeRelayAPI{},
-		make(<-chan bool),
+		make(chan bool),
 	)
 
 	retriever.InitializeRelayServers(logrus.WithField("test", "relay"))
@@ -74,7 +74,7 @@ func TestRelayRetrieverSync(t *testing.T) {
 		"server",
 		&FakeFedAPI{},
 		&FakeRelayAPI{},
-		make(<-chan bool),
+		make(chan bool),
 	)
 
 	retriever.InitializeRelayServers(logrus.WithField("test", "relay"))