diff --git a/build/gobind-pinecone/monolith.go b/build/gobind-pinecone/monolith.go
index 4f61e6936..8ae010111 100644
--- a/build/gobind-pinecone/monolith.go
+++ b/build/gobind-pinecone/monolith.go
@@ -11,6 +11,7 @@ import (
 	"io"
 	"io/ioutil"
 	"log"
+	"math"
 	"net"
 	"net/http"
 	"os"
@@ -94,12 +95,12 @@ func (m *DendriteMonolith) SetMulticastEnabled(enabled bool) {
 }
 
 func (m *DendriteMonolith) SetStaticPeer(uri string) {
+	m.staticPeerMutex.Lock()
+	m.staticPeerURI = uri
+	m.staticPeerMutex.Unlock()
 	m.DisconnectType(pineconeRouter.PeerTypeRemote)
 	if uri != "" {
-		m.staticPeerMutex.Lock()
-		m.staticPeerURI = uri
-		m.staticPeerMutex.Unlock()
-		go conn.ConnectToPeer(m.PineconeRouter, uri)
+		m.staticPeerConnect()
 	}
 }
 
@@ -194,6 +195,21 @@ func (m *DendriteMonolith) RegisterDevice(localpart, deviceID string) (string, e
 	return loginRes.Device.AccessToken, nil
 }
 
+func (m *DendriteMonolith) staticPeerConnect() {
+	m.staticPeerMutex.RLock()
+	uri := m.staticPeerURI
+	m.staticPeerMutex.RUnlock()
+	if uri == "" {
+		return
+	}
+	if err := conn.ConnectToPeer(m.PineconeRouter, uri); err != nil {
+		exp := time.Second * time.Duration(math.Exp2(float64(m.staticPeerAttempts.Inc())))
+		time.AfterFunc(exp, m.staticPeerConnect)
+	} else {
+		m.staticPeerAttempts.Store(0)
+	}
+}
+
 // nolint:gocyclo
 func (m *DendriteMonolith) Start() {
 	m.config = yggdrasilConfig.GenerateConfig()
@@ -256,11 +272,9 @@ func (m *DendriteMonolith) Start() {
 	m.PineconeMulticast = pineconeMulticast.NewMulticast(logger, m.PineconeRouter)
 
 	m.PineconeRouter.SetDisconnectedCallback(func(port pineconeTypes.SwitchPortID, public pineconeTypes.PublicKey, peertype int, err error) {
-		m.staticPeerMutex.RLock()
-		uri := m.staticPeerURI
-		m.staticPeerMutex.RUnlock()
-		if peertype == pineconeRouter.PeerTypeRemote && uri != "" && err != nil {
-			conn.ConnectToPeer(m.PineconeRouter, uri)
+		if peertype == pineconeRouter.PeerTypeRemote && err != nil {
+			m.staticPeerAttempts.Store(0)
+			time.AfterFunc(time.Second, m.staticPeerConnect)
 		}
 	})
 
diff --git a/cmd/dendrite-demo-pinecone/conn/client.go b/cmd/dendrite-demo-pinecone/conn/client.go
index 9b51c27c0..bf23085d0 100644
--- a/cmd/dendrite-demo-pinecone/conn/client.go
+++ b/cmd/dendrite-demo-pinecone/conn/client.go
@@ -1,6 +1,7 @@
 package conn
 
 import (
+	"fmt"
 	"net"
 	"net/http"
 	"strings"
@@ -8,35 +9,31 @@ import (
 	"github.com/gorilla/websocket"
 	"github.com/matrix-org/dendrite/setup"
 	"github.com/matrix-org/gomatrixserverlib"
-	"github.com/sirupsen/logrus"
 
 	pineconeRouter "github.com/matrix-org/pinecone/router"
 	pineconeSessions "github.com/matrix-org/pinecone/sessions"
 )
 
-func ConnectToPeer(pRouter *pineconeRouter.Router, peer string) {
+func ConnectToPeer(pRouter *pineconeRouter.Router, peer string) error {
 	var parent net.Conn
 	if strings.HasPrefix(peer, "ws://") || strings.HasPrefix(peer, "wss://") {
 		c, _, err := websocket.DefaultDialer.Dial(peer, nil)
 		if err != nil {
-			logrus.WithError(err).Errorf("Failed to connect to Pinecone static peer %q via WebSockets", peer)
-			return
+			return fmt.Errorf("websocket.DefaultDialer.Dial: %w", err)
 		}
 		parent = WrapWebSocketConn(c)
 	} else {
 		var err error
 		parent, err = net.Dial("tcp", peer)
 		if err != nil {
-			logrus.WithError(err).Errorf("Failed to connect to Pinecone static peer %q via TCP", peer)
-			return
+			return fmt.Errorf("net.Dial: %w", err)
 		}
 	}
 	if parent == nil {
-		return
-	}
-	if _, err := pRouter.AuthenticatedConnect(parent, "static", pineconeRouter.PeerTypeRemote); err != nil {
-		logrus.WithError(err).Errorf("Failed to connect Pinecone static peer to switch")
+		return fmt.Errorf("failed to wrap connection")
 	}
+	_, err := pRouter.AuthenticatedConnect(parent, "static", pineconeRouter.PeerTypeRemote)
+	return err
 }
 
 type RoundTripper struct {
diff --git a/cmd/dendrite-demo-pinecone/main.go b/cmd/dendrite-demo-pinecone/main.go
index 6d065886a..074fb0289 100644
--- a/cmd/dendrite-demo-pinecone/main.go
+++ b/cmd/dendrite-demo-pinecone/main.go
@@ -23,6 +23,7 @@ import (
 	"fmt"
 	"io/ioutil"
 	"log"
+	"math"
 	"net"
 	"net/http"
 	"os"
@@ -47,6 +48,7 @@ import (
 	"github.com/matrix-org/dendrite/setup/config"
 	"github.com/matrix-org/dendrite/userapi"
 	"github.com/matrix-org/gomatrixserverlib"
+	"go.uber.org/atomic"
 
 	pineconeMulticast "github.com/matrix-org/pinecone/multicast"
 	pineconeRouter "github.com/matrix-org/pinecone/router"
@@ -92,10 +94,6 @@ func main() {
 	logger := log.New(os.Stdout, "", 0)
 	pRouter := pineconeRouter.NewRouter(logger, "dendrite", sk, pk, nil)
 
-	if instancePeer != nil && *instancePeer != "" {
-		go conn.ConnectToPeer(pRouter, *instancePeer)
-	}
-
 	go func() {
 		listener, err := net.Listen("tcp", *instanceListen)
 		if err != nil {
@@ -125,12 +123,27 @@ func main() {
 	pMulticast := pineconeMulticast.NewMulticast(logger, pRouter)
 	pMulticast.Start()
 
-	pRouter.SetDisconnectedCallback(func(port pineconeTypes.SwitchPortID, public pineconeTypes.PublicKey, peertype int, err error) {
+	var staticPeerAttempts atomic.Uint32
+	var connectToStaticPeer func()
+	connectToStaticPeer = func() {
 		uri := *instancePeer
-		if peertype == pineconeRouter.PeerTypeRemote && uri != "" && err != nil {
-			conn.ConnectToPeer(pRouter, uri)
+		if uri == "" {
+			return
+		}
+		if err := conn.ConnectToPeer(pRouter, uri); err != nil {
+			exp := time.Second * time.Duration(math.Exp2(float64(staticPeerAttempts.Inc())))
+			time.AfterFunc(exp, connectToStaticPeer)
+		} else {
+			staticPeerAttempts.Store(0)
+		}
+	}
+	pRouter.SetDisconnectedCallback(func(port pineconeTypes.SwitchPortID, public pineconeTypes.PublicKey, peertype int, err error) {
+		if peertype == pineconeRouter.PeerTypeRemote && err != nil {
+			staticPeerAttempts.Store(0)
+			time.AfterFunc(time.Second, connectToStaticPeer)
 		}
 	})
+	go connectToStaticPeer()
 
 	cfg := &config.Dendrite{}
 	cfg.Defaults()