diff --git a/.gitignore b/.gitignore
index 5fe29db..140675b 100644
--- a/.gitignore
+++ b/.gitignore
@@ -242,5 +242,9 @@ punchr.gz
 
 dist/
 
+**/*api-key.txt
+
+gui/client/**.app
+
 # Nix build result symlink
 result
\ No newline at end of file
diff --git a/cmd/server/grpc.go b/cmd/server/grpc.go
index f144043..d35ff4e 100644
--- a/cmd/server/grpc.go
+++ b/cmd/server/grpc.go
@@ -99,6 +99,10 @@ func (s Server) GetAddrInfo(ctx context.Context, req *pb.GetAddrInfoRequest) (*p
 		return nil, errors.Wrap(err, "get client peer from db")
 	}
 
+	if len(dbHosts) == 0 {
+		return nil, errors.Wrap(err, "please restart the client")
+	}
+
 	dbHostIDs := make([]string, len(dbHosts))
 	for i, dbHost := range dbHosts {
 		dbHostIDs[i] = strconv.FormatInt(dbHost.ID, 10)
@@ -181,7 +185,7 @@ LIMIT 1
 	}
 	remoteID, err := peer.Decode(remoteMultiHash)
 	if err != nil {
-		return nil, errors.Wrap(err, "query addr infos")
+		return nil, errors.Wrap(err, "decode remote multi hash")
 	}
 
 	remoteIDBytes, err := remoteID.Marshal()
@@ -266,7 +270,7 @@ LIMIT 1
 
 	remoteID, err := peer.Decode(remoteMultiHash)
 	if err != nil {
-		return nil, errors.Wrap(err, "query addr infos")
+		return nil, errors.Wrap(err, "decode remote multi hash")
 	}
 
 	remoteIDBytes, err := remoteID.Marshal()
diff --git a/go.mod b/go.mod
index 71730c1..379e592 100644
--- a/go.mod
+++ b/go.mod
@@ -4,6 +4,7 @@ go 1.18
 
 require (
 	fyne.io/fyne/v2 v2.2.3
+	github.com/emersion/go-autostart v0.0.0-20210130080809-00ed301c8e9a
 	github.com/friendsofgo/errors v0.9.2
 	github.com/golang-migrate/migrate/v4 v4.15.2
 	github.com/grpc-ecosystem/go-grpc-middleware v1.3.0
diff --git a/go.sum b/go.sum
index 5a5e6f8..ad96dd6 100644
--- a/go.sum
+++ b/go.sum
@@ -431,6 +431,8 @@ github.com/elastic/gosigar v0.12.0/go.mod h1:iXRIGg2tLnu7LBdpqzyQfGDEidKCfWcCMS0
 github.com/elastic/gosigar v0.14.2 h1:Dg80n8cr90OZ7x+bAax/QjoW/XqTI11RmA79ZwIm9/4=
 github.com/elastic/gosigar v0.14.2/go.mod h1:iXRIGg2tLnu7LBdpqzyQfGDEidKCfWcCMS0WKyPWoMs=
 github.com/elazarl/goproxy v0.0.0-20180725130230-947c36da3153/go.mod h1:/Zj4wYkgs4iZTTu3o/KG3Itv/qCCa8VVMlb3i9OVuzc=
+github.com/emersion/go-autostart v0.0.0-20210130080809-00ed301c8e9a h1:M88ob4TyDnEqNuL3PgsE/p3bDujfspnulR+0dQWNYZs=
+github.com/emersion/go-autostart v0.0.0-20210130080809-00ed301c8e9a/go.mod h1:buzQsO8HHkZX2Q45fdfGH1xejPjuDQaXH8btcYMFzPM=
 github.com/emicklei/go-restful v0.0.0-20170410110728-ff4f55a20633/go.mod h1:otzb+WCGbkyDHkqmQmT5YD2WR4BBwUdeQoFo8l/7tVs=
 github.com/emicklei/go-restful v2.9.5+incompatible/go.mod h1:otzb+WCGbkyDHkqmQmT5YD2WR4BBwUdeQoFo8l/7tVs=
 github.com/envoyproxy/go-control-plane v0.9.0/go.mod h1:YTl/9mNaCwkRvm6d1a2C3ymFceY/DCBVvsKhRF0iEA4=
diff --git a/gui/client/client.go b/gui/client/client.go
index 2bb35a9..14b7ba5 100644
--- a/gui/client/client.go
+++ b/gui/client/client.go
@@ -3,6 +3,7 @@ package main
 import (
 	"context"
 	"io"
+	"os"
 
 	"fyne.io/fyne/v2"
 	"fyne.io/fyne/v2/app"
@@ -11,6 +12,7 @@ import (
 	"fyne.io/fyne/v2/layout"
 	"fyne.io/fyne/v2/storage"
 	"fyne.io/fyne/v2/widget"
+	"github.com/emersion/go-autostart"
 	"github.com/friendsofgo/errors"
 	log "github.com/sirupsen/logrus"
 
@@ -26,9 +28,22 @@ var (
 	menuItemStatus = fyne.NewMenuItem("", nil)
 	menuItemToggle = fyne.NewMenuItem("", nil)
 	menuItemApiKey = fyne.NewMenuItem("Set API Key", nil)
+	menuItemLogin  = fyne.NewMenuItem("", nil)
 )
 
 func main() {
+	execPath, err := os.Executable()
+	if err != nil {
+		log.WithError(err).Errorln("Could not determine executable path")
+		os.Exit(1)
+	}
+
+	autostartApp := &autostart.App{
+		Name:        "com.protocol.ai.punchr",
+		DisplayName: "Punchr Client",
+		Exec:        []string{execPath},
+	}
+
 	a := app.New()
 	a.SetIcon(gloveInactiveEmoji)
 
@@ -52,16 +67,36 @@ func main() {
 	menuItemApiKey.Action = func() {
 		p.ShowApiKeyDialog()
 	}
+	menuItemLogin.Action = func() {
+		if autostartApp.IsEnabled() {
+			if err := autostartApp.Disable(); err != nil {
+				log.WithError(err).Warnln("error")
+			}
+			menuItemLogin.Label = "🔴 Launch on Login: Disabled"
+		} else {
+			log.Println("Enabling app...")
+			if err := autostartApp.Enable(); err != nil {
+				log.WithError(err).Warnln("error")
+			}
+			menuItemLogin.Label = "🟢 Launch on Login: Enabled"
+		}
+		sysTrayMenu.Refresh()
+	}
 
-	sysTrayMenu = fyne.NewMenu("Punchr", menuItemStatus, fyne.NewMenuItemSeparator(), menuItemToggle, menuItemApiKey)
+	sysTrayMenu = fyne.NewMenu("Punchr", menuItemStatus, fyne.NewMenuItemSeparator(), menuItemToggle, menuItemApiKey, menuItemLogin)
 	desk.SetSystemTrayMenu(sysTrayMenu)
 
 	if p.apiKey == "" {
 		menuItemStatus.Label = "No API-Key"
 		menuItemToggle.Disabled = true
 	} else {
-		menuItemStatus.Label = "API-Key: " + p.apiKey
-		menuItemToggle.Label = "Start Hole Punching"
+		go p.StartHolePunching()
+	}
+
+	if autostartApp.IsEnabled() {
+		menuItemLogin.Label = "🟢 Launch on Login: Enabled"
+	} else {
+		menuItemLogin.Label = "🔴 Launch on Login: Disabled"
 	}
 
 	sysTrayMenu.Refresh()
@@ -138,7 +173,7 @@ func (p *Punchr) StartHolePunching() {
 
 	p.isHolePunching = true
 	desk.SetSystemTrayIcon(gloveActiveEmoji)
-	menuItemStatus.Label = "Running..."
+	menuItemStatus.Label = "🟢 Running..."
 	menuItemToggle.Label = "Stop Hole Punching"
 	sysTrayMenu.Refresh()
 
diff --git a/pkg/client/host.go b/pkg/client/host.go
index 77d8f64..a8933ec 100644
--- a/pkg/client/host.go
+++ b/pkg/client/host.go
@@ -36,7 +36,7 @@ type Host struct {
 	holePunchEventsPeers sync.Map
 	bpAddrInfos          []peer.AddrInfo
 	rcmgr                *ResourceManager
-	maddrs               map[multiaddr.Multiaddr]struct{}
+	maddrs               map[string]struct{}
 }
 
 func InitHost(c *cli.Context, privKey crypto.PrivKey) (*Host, error) {
@@ -71,7 +71,7 @@ func InitHost(c *cli.Context, privKey crypto.PrivKey) (*Host, error) {
 		holePunchEventsPeers: sync.Map{},
 		bpAddrInfos:          bpAddrInfos,
 		rcmgr:                rcmgr,
-		maddrs:               map[multiaddr.Multiaddr]struct{}{},
+		maddrs:               map[string]struct{}{},
 	}
 
 	// Configure new libp2p host
@@ -159,7 +159,7 @@ func (h *Host) WaitForPublicAddr(ctx context.Context) error {
 			logEntry.Debug("Found >= 1 public addresses!")
 			for _, maddr := range h.Host.Addrs() {
 				if manet.IsPublicAddr(maddr) {
-					h.maddrs[maddr] = struct{}{}
+					h.maddrs[maddr.String()] = struct{}{}
 				}
 			}
 
@@ -224,9 +224,15 @@ func (h *Host) HolePunch(ctx context.Context, addrInfo peer.AddrInfo) *HolePunch
 
 	// Track open connections after the hole punch
 	defer func() {
+		deduplicate := map[string]struct{}{}
 		for _, conn := range h.Network().ConnsToPeer(addrInfo.ID) {
+			if _, found := deduplicate[conn.RemoteMultiaddr().String()]; found {
+				continue
+			}
 			hpState.OpenMaddrs = append(hpState.OpenMaddrs, conn.RemoteMultiaddr())
+			deduplicate[conn.RemoteMultiaddr().String()] = struct{}{}
 		}
+		fmt.Println("hpState.OpenMaddrs", hpState.OpenMaddrs)
 		hpState.HasDirectConns = h.hasDirectConnToPeer(addrInfo.ID)
 	}()
 
diff --git a/pkg/client/punchr.go b/pkg/client/punchr.go
index 8be51d2..53af4d5 100644
--- a/pkg/client/punchr.go
+++ b/pkg/client/punchr.go
@@ -228,7 +228,7 @@ func (p Punchr) StartHolePunching(ctx context.Context) error {
 		if !p.disableRouterCheck {
 			// Check if the multi addresses have changed - if that's the case we have switched networks
 			for _, maddr := range h.Addrs() {
-				if _, found := h.maddrs[maddr]; found {
+				if _, found := h.maddrs[maddr.String()]; found {
 					continue
 				}
 
@@ -240,9 +240,9 @@ func (p Punchr) StartHolePunching(ctx context.Context) error {
 				}
 
 				// Update list of multi addresses
-				h.maddrs = map[multiaddr.Multiaddr]struct{}{}
+				h.maddrs = map[string]struct{}{}
 				for _, newMaddr := range h.Addrs() {
-					h.maddrs[newMaddr] = struct{}{}
+					h.maddrs[newMaddr.String()] = struct{}{}
 				}
 
 				break