diff --git a/cli/ssh.go b/cli/ssh.go
index 51f53e10bcbd2..4adbf12cccf7e 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -16,7 +16,6 @@ import (
 	"path/filepath"
 	"regexp"
 	"slices"
-	"strconv"
 	"strings"
 	"sync"
 	"time"
@@ -31,7 +30,6 @@ import (
 	"golang.org/x/term"
 	"golang.org/x/xerrors"
 	"gvisor.dev/gvisor/pkg/tcpip/adapters/gonet"
-	"tailscale.com/tailcfg"
 	"tailscale.com/types/netlogtype"
 
 	"cdr.dev/slog"
@@ -40,11 +38,13 @@ import (
 	"github.com/coder/coder/v2/cli/cliui"
 	"github.com/coder/coder/v2/cli/cliutil"
 	"github.com/coder/coder/v2/coderd/autobuild/notify"
+	"github.com/coder/coder/v2/coderd/util/maps"
 	"github.com/coder/coder/v2/coderd/util/ptr"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 	"github.com/coder/coder/v2/cryptorand"
 	"github.com/coder/coder/v2/pty"
+	"github.com/coder/coder/v2/tailnet"
 	"github.com/coder/quartz"
 	"github.com/coder/retry"
 	"github.com/coder/serpent"
@@ -1456,28 +1456,6 @@ func collectNetworkStats(ctx context.Context, agentConn *workspacesdk.AgentConn,
 	}
 	node := agentConn.Node()
 	derpMap := agentConn.DERPMap()
-	derpLatency := map[string]float64{}
-
-	// Convert DERP region IDs to friendly names for display in the UI.
-	for rawRegion, latency := range node.DERPLatency {
-		regionParts := strings.SplitN(rawRegion, "-", 2)
-		regionID, err := strconv.Atoi(regionParts[0])
-		if err != nil {
-			continue
-		}
-		region, found := derpMap.Regions[regionID]
-		if !found {
-			// It's possible that a workspace agent is using an old DERPMap
-			// and reports regions that do not exist. If that's the case,
-			// report the region as unknown!
-			region = &tailcfg.DERPRegion{
-				RegionID:   regionID,
-				RegionName: fmt.Sprintf("Unnamed %d", regionID),
-			}
-		}
-		// Convert the microseconds to milliseconds.
-		derpLatency[region.RegionName] = latency * 1000
-	}
 
 	totalRx := uint64(0)
 	totalTx := uint64(0)
@@ -1491,27 +1469,20 @@ func collectNetworkStats(ctx context.Context, agentConn *workspacesdk.AgentConn,
 	uploadSecs := float64(totalTx) / dur.Seconds()
 	downloadSecs := float64(totalRx) / dur.Seconds()
 
-	// Sometimes the preferred DERP doesn't match the one we're actually
-	// connected with. Perhaps because the agent prefers a different DERP and
-	// we're using that server instead.
-	preferredDerpID := node.PreferredDERP
-	if pingResult.DERPRegionID != 0 {
-		preferredDerpID = pingResult.DERPRegionID
-	}
-	preferredDerp, ok := derpMap.Regions[preferredDerpID]
-	preferredDerpName := fmt.Sprintf("Unnamed %d", preferredDerpID)
-	if ok {
-		preferredDerpName = preferredDerp.RegionName
-	}
+	preferredDerpName := tailnet.ExtractPreferredDERPName(pingResult, node, derpMap)
+	derpLatency := tailnet.ExtractDERPLatency(node, derpMap)
 	if _, ok := derpLatency[preferredDerpName]; !ok {
 		derpLatency[preferredDerpName] = 0
 	}
+	derpLatencyMs := maps.Map(derpLatency, func(dur time.Duration) float64 {
+		return float64(dur) / float64(time.Millisecond)
+	})
 
 	return &sshNetworkStats{
 		P2P:              p2p,
 		Latency:          float64(latency.Microseconds()) / 1000,
 		PreferredDERP:    preferredDerpName,
-		DERPLatency:      derpLatency,
+		DERPLatency:      derpLatencyMs,
 		UploadBytesSec:   int64(uploadSecs),
 		DownloadBytesSec: int64(downloadSecs),
 	}, nil
diff --git a/coderd/database/db2sdk/db2sdk.go b/coderd/database/db2sdk/db2sdk.go
index 40b1423a0f730..9978aa0bcaff5 100644
--- a/coderd/database/db2sdk/db2sdk.go
+++ b/coderd/database/db2sdk/db2sdk.go
@@ -47,14 +47,6 @@ func ListLazy[F any, T any](convert func(F) T) func(list []F) []T {
 	}
 }
 
-func Map[K comparable, F any, T any](params map[K]F, convert func(F) T) map[K]T {
-	into := make(map[K]T)
-	for k, item := range params {
-		into[k] = convert(item)
-	}
-	return into
-}
-
 type ExternalAuthMeta struct {
 	Authenticated bool
 	ValidateError string
diff --git a/coderd/util/maps/maps.go b/coderd/util/maps/maps.go
index 8aaa6669cb8af..6a858bf3f7085 100644
--- a/coderd/util/maps/maps.go
+++ b/coderd/util/maps/maps.go
@@ -6,6 +6,14 @@ import (
 	"golang.org/x/exp/constraints"
 )
 
+func Map[K comparable, F any, T any](params map[K]F, convert func(F) T) map[K]T {
+	into := make(map[K]T)
+	for k, item := range params {
+		into[k] = convert(item)
+	}
+	return into
+}
+
 // Subset returns true if all the keys of a are present
 // in b and have the same values.
 // If the corresponding value of a[k] is the zero value in
diff --git a/tailnet/derpmap.go b/tailnet/derpmap.go
index e2722c1ff9ab4..6f284dad05991 100644
--- a/tailnet/derpmap.go
+++ b/tailnet/derpmap.go
@@ -8,8 +8,11 @@ import (
 	"net/http"
 	"os"
 	"strconv"
+	"strings"
+	"time"
 
 	"golang.org/x/xerrors"
+	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/tailcfg"
 )
 
@@ -152,6 +155,49 @@ regionLoop:
 	return derpMap, nil
 }
 
+func ExtractPreferredDERPName(pingResult *ipnstate.PingResult, node *Node, derpMap *tailcfg.DERPMap) string {
+	// Sometimes the preferred DERP doesn't match the one we're actually
+	// connected with. Perhaps because the agent prefers a different DERP and
+	// we're using that server instead.
+	preferredDerpID := node.PreferredDERP
+	if pingResult.DERPRegionID != 0 {
+		preferredDerpID = pingResult.DERPRegionID
+	}
+	preferredDerp, ok := derpMap.Regions[preferredDerpID]
+	preferredDerpName := fmt.Sprintf("Unnamed %d", preferredDerpID)
+	if ok {
+		preferredDerpName = preferredDerp.RegionName
+	}
+
+	return preferredDerpName
+}
+
+// ExtractDERPLatency extracts a map of derp region names to their latencies
+func ExtractDERPLatency(node *Node, derpMap *tailcfg.DERPMap) map[string]time.Duration {
+	latencyMs := make(map[string]time.Duration)
+
+	// Convert DERP region IDs to friendly names for display in the UI.
+	for rawRegion, latency := range node.DERPLatency {
+		regionParts := strings.SplitN(rawRegion, "-", 2)
+		regionID, err := strconv.Atoi(regionParts[0])
+		if err != nil {
+			continue
+		}
+		region, found := derpMap.Regions[regionID]
+		if !found {
+			// It's possible that a workspace agent is using an old DERPMap
+			// and reports regions that do not exist. If that's the case,
+			// report the region as unknown!
+			region = &tailcfg.DERPRegion{
+				RegionID:   regionID,
+				RegionName: fmt.Sprintf("Unnamed %d", regionID),
+			}
+		}
+		latencyMs[region.RegionName] = time.Duration(latency * float64(time.Second))
+	}
+	return latencyMs
+}
+
 // CompareDERPMaps returns true if the given DERPMaps are equivalent. Ordering
 // of slices is ignored.
 //
diff --git a/tailnet/derpmap_test.go b/tailnet/derpmap_test.go
index a91969bfeca09..c723437cad0d2 100644
--- a/tailnet/derpmap_test.go
+++ b/tailnet/derpmap_test.go
@@ -10,6 +10,7 @@ import (
 	"testing"
 
 	"github.com/stretchr/testify/require"
+	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/tailcfg"
 
 	"github.com/coder/coder/v2/tailnet"
@@ -162,3 +163,111 @@ func TestNewDERPMap(t *testing.T) {
 		require.ErrorContains(t, err, "DERP map has no DERP nodes")
 	})
 }
+
+func TestExtractDERPLatency(t *testing.T) {
+	t.Parallel()
+
+	derpMap := &tailcfg.DERPMap{
+		Regions: map[int]*tailcfg.DERPRegion{
+			1: {
+				RegionID:   1,
+				RegionName: "Region One",
+				Nodes: []*tailcfg.DERPNode{
+					{Name: "node1", RegionID: 1},
+				},
+			},
+			2: {
+				RegionID:   2,
+				RegionName: "Region Two",
+				Nodes: []*tailcfg.DERPNode{
+					{Name: "node2", RegionID: 2},
+				},
+			},
+		},
+	}
+
+	t.Run("Basic", func(t *testing.T) {
+		t.Parallel()
+		node := &tailnet.Node{
+			DERPLatency: map[string]float64{
+				"1-node1": 0.05,
+				"2-node2": 0.1,
+			},
+		}
+		latencyMs := tailnet.ExtractDERPLatency(node, derpMap)
+		require.EqualValues(t, 50, latencyMs["Region One"].Milliseconds())
+		require.EqualValues(t, 100, latencyMs["Region Two"].Milliseconds())
+		require.Len(t, latencyMs, 2)
+	})
+
+	t.Run("UnknownRegion", func(t *testing.T) {
+		t.Parallel()
+		node := &tailnet.Node{
+			DERPLatency: map[string]float64{
+				"999-node999": 0.2,
+			},
+		}
+		latencyMs := tailnet.ExtractDERPLatency(node, derpMap)
+		require.EqualValues(t, 200, latencyMs["Unnamed 999"].Milliseconds())
+		require.Len(t, latencyMs, 1)
+	})
+
+	t.Run("InvalidRegionFormat", func(t *testing.T) {
+		t.Parallel()
+		node := &tailnet.Node{
+			DERPLatency: map[string]float64{
+				"invalid":  0.3,
+				"1-node1":  0.05,
+				"abc-node": 0.15,
+			},
+		}
+		latencyMs := tailnet.ExtractDERPLatency(node, derpMap)
+		require.EqualValues(t, 50, latencyMs["Region One"].Milliseconds())
+		require.Len(t, latencyMs, 1)
+		require.NotContains(t, latencyMs, "invalid")
+		require.NotContains(t, latencyMs, "abc-node")
+	})
+
+	t.Run("EmptyInput", func(t *testing.T) {
+		t.Parallel()
+		node := &tailnet.Node{
+			DERPLatency: map[string]float64{},
+		}
+		latencyMs := tailnet.ExtractDERPLatency(node, derpMap)
+		require.Empty(t, latencyMs)
+	})
+}
+
+func TestExtractPreferredDERPName(t *testing.T) {
+	t.Parallel()
+	derpMap := &tailcfg.DERPMap{
+		Regions: map[int]*tailcfg.DERPRegion{
+			1: {RegionName: "New York"},
+			2: {RegionName: "London"},
+		},
+	}
+
+	t.Run("UsesPingRegion", func(t *testing.T) {
+		t.Parallel()
+		pingResult := &ipnstate.PingResult{DERPRegionID: 2}
+		node := &tailnet.Node{PreferredDERP: 1}
+		result := tailnet.ExtractPreferredDERPName(pingResult, node, derpMap)
+		require.Equal(t, "London", result)
+	})
+
+	t.Run("UsesNodePreferred", func(t *testing.T) {
+		t.Parallel()
+		pingResult := &ipnstate.PingResult{DERPRegionID: 0}
+		node := &tailnet.Node{PreferredDERP: 1}
+		result := tailnet.ExtractPreferredDERPName(pingResult, node, derpMap)
+		require.Equal(t, "New York", result)
+	})
+
+	t.Run("UnknownRegion", func(t *testing.T) {
+		t.Parallel()
+		pingResult := &ipnstate.PingResult{DERPRegionID: 99}
+		node := &tailnet.Node{PreferredDERP: 1}
+		result := tailnet.ExtractPreferredDERPName(pingResult, node, derpMap)
+		require.Equal(t, "Unnamed 99", result)
+	})
+}
diff --git a/vpn/client.go b/vpn/client.go
index da066bbcd62b3..e3f3e767fc477 100644
--- a/vpn/client.go
+++ b/vpn/client.go
@@ -5,11 +5,14 @@ import (
 	"net/http"
 	"net/netip"
 	"net/url"
+	"time"
 
 	"golang.org/x/xerrors"
 
+	"tailscale.com/ipn/ipnstate"
 	"tailscale.com/net/dns"
 	"tailscale.com/net/netmon"
+	"tailscale.com/tailcfg"
 	"tailscale.com/wgengine/router"
 
 	"github.com/google/uuid"
@@ -27,6 +30,9 @@ import (
 type Conn interface {
 	CurrentWorkspaceState() (tailnet.WorkspaceUpdate, error)
 	GetPeerDiagnostics(peerID uuid.UUID) tailnet.PeerDiagnostics
+	Ping(ctx context.Context, agentID uuid.UUID) (time.Duration, bool, *ipnstate.PingResult, error)
+	Node() *tailnet.Node
+	DERPMap() *tailcfg.DERPMap
 	Close() error
 }
 
@@ -38,6 +44,10 @@ type vpnConn struct {
 	updatesCtrl *tailnet.TunnelAllWorkspaceUpdatesController
 }
 
+func (c *vpnConn) Ping(ctx context.Context, agentID uuid.UUID) (time.Duration, bool, *ipnstate.PingResult, error) {
+	return c.Conn.Ping(ctx, tailnet.TailscaleServicePrefix.AddrFromUUID(agentID))
+}
+
 func (c *vpnConn) CurrentWorkspaceState() (tailnet.WorkspaceUpdate, error) {
 	return c.updatesCtrl.CurrentState()
 }
diff --git a/vpn/speaker_internal_test.go b/vpn/speaker_internal_test.go
index 2f3d131093382..433868851a5bc 100644
--- a/vpn/speaker_internal_test.go
+++ b/vpn/speaker_internal_test.go
@@ -23,6 +23,8 @@ func TestMain(m *testing.M) {
 	goleak.VerifyTestMain(m, testutil.GoleakOptions...)
 }
 
+const expectedHandshake = "codervpn tunnel 1.2\n"
+
 // TestSpeaker_RawPeer tests the speaker with a peer that we simulate by directly making reads and
 // writes to the other end of the pipe. There should be at least one test that does this, rather
 // than use 2 speakers so that we don't have a bug where we don't adhere to the stated protocol, but
@@ -48,8 +50,6 @@ func TestSpeaker_RawPeer(t *testing.T) {
 		errCh <- err
 	}()
 
-	expectedHandshake := "codervpn tunnel 1.1\n"
-
 	b := make([]byte, 256)
 	n, err := mp.Read(b)
 	require.NoError(t, err)
@@ -157,8 +157,6 @@ func TestSpeaker_OversizeHandshake(t *testing.T) {
 		errCh <- err
 	}()
 
-	expectedHandshake := "codervpn tunnel 1.1\n"
-
 	b := make([]byte, 256)
 	n, err := mp.Read(b)
 	require.NoError(t, err)
@@ -210,7 +208,6 @@ func TestSpeaker_HandshakeInvalid(t *testing.T) {
 			_, err = mp.Write([]byte(tc.handshake))
 			require.NoError(t, err)
 
-			expectedHandshake := "codervpn tunnel 1.1\n"
 			b := make([]byte, 256)
 			n, err := mp.Read(b)
 			require.NoError(t, err)
@@ -248,8 +245,6 @@ func TestSpeaker_CorruptMessage(t *testing.T) {
 		errCh <- err
 	}()
 
-	expectedHandshake := "codervpn tunnel 1.1\n"
-
 	b := make([]byte, 256)
 	n, err := mp.Read(b)
 	require.NoError(t, err)
diff --git a/vpn/tunnel.go b/vpn/tunnel.go
index 6c71aecaa0965..aa1d0e32ef5b9 100644
--- a/vpn/tunnel.go
+++ b/vpn/tunnel.go
@@ -19,6 +19,7 @@ import (
 	"github.com/google/uuid"
 	"github.com/tailscale/wireguard-go/tun"
 	"golang.org/x/xerrors"
+	"google.golang.org/protobuf/types/known/durationpb"
 	"google.golang.org/protobuf/types/known/timestamppb"
 	"tailscale.com/net/dns"
 	"tailscale.com/net/netmon"
@@ -32,9 +33,9 @@ import (
 	"github.com/coder/coder/v2/tailnet"
 )
 
-// netStatusInterval is the interval at which the tunnel sends network status updates to the manager.
-// This is currently only used to keep `last_handshake` up to date.
-const netStatusInterval = 10 * time.Second
+// netStatusInterval is the interval at which the tunnel records latencies,
+// and sends network status updates to the manager.
+const netStatusInterval = 5 * time.Second
 
 type Tunnel struct {
 	speaker[*TunnelMessage, *ManagerMessage, ManagerMessage]
@@ -86,8 +87,9 @@ func NewTunnel(
 			ctx:         uCtx,
 			cancel:      uCancel,
 			netLoopDone: make(chan struct{}),
+			logger:      logger,
 			uSendCh:     s.sendCh,
-			agents:      map[uuid.UUID]tailnet.Agent{},
+			agents:      map[uuid.UUID]agentWithPing{},
 			workspaces:  map[uuid.UUID]tailnet.Workspace{},
 			clock:       quartz.NewReal(),
 		},
@@ -344,10 +346,12 @@ type updater struct {
 	cancel      context.CancelFunc
 	netLoopDone chan struct{}
 
+	logger slog.Logger
+
 	mu      sync.Mutex
 	uSendCh chan<- *TunnelMessage
 	// agents contains the agents that are currently connected to the tunnel.
-	agents map[uuid.UUID]tailnet.Agent
+	agents map[uuid.UUID]agentWithPing
 	// workspaces contains the workspaces to which agents are currently connected via the tunnel.
 	workspaces map[uuid.UUID]tailnet.Workspace
 	conn       Conn
@@ -355,6 +359,26 @@ type updater struct {
 	clock quartz.Clock
 }
 
+type agentWithPing struct {
+	tailnet.Agent
+	// non-nil if a successful ping has been made
+	lastPing *lastPing
+}
+
+func (a *agentWithPing) Clone() *agentWithPing {
+	return &agentWithPing{
+		Agent:    a.Agent.Clone(),
+		lastPing: a.lastPing,
+	}
+}
+
+type lastPing struct {
+	pingDur              time.Duration
+	didP2p               bool
+	preferredDerp        string
+	preferredDerpLatency *time.Duration
+}
+
 // Update pushes a workspace update to the manager
 func (u *updater) Update(update tailnet.WorkspaceUpdate) error {
 	u.mu.Lock()
@@ -412,10 +436,21 @@ func (u *updater) createPeerUpdateLocked(update tailnet.WorkspaceUpdate) *PeerUp
 		DeletedAgents:      make([]*Agent, len(update.DeletedAgents)),
 	}
 
+	var upsertedAgentsWithPing []*agentWithPing
+
 	// save the workspace update to the tunnel's state, such that it can
 	// be used to populate automated peer updates.
 	for _, agent := range update.UpsertedAgents {
-		u.agents[agent.ID] = agent.Clone()
+		var lastPing *lastPing
+		if existing, ok := u.agents[agent.ID]; ok {
+			lastPing = existing.lastPing
+		}
+		upsertedAgent := agentWithPing{
+			Agent:    agent.Clone(),
+			lastPing: lastPing,
+		}
+		u.agents[agent.ID] = upsertedAgent
+		upsertedAgentsWithPing = append(upsertedAgentsWithPing, &upsertedAgent)
 	}
 	for _, agent := range update.DeletedAgents {
 		delete(u.agents, agent.ID)
@@ -435,7 +470,7 @@ func (u *updater) createPeerUpdateLocked(update tailnet.WorkspaceUpdate) *PeerUp
 		}
 	}
 
-	upsertedAgents := u.convertAgentsLocked(update.UpsertedAgents)
+	upsertedAgents := u.convertAgentsLocked(upsertedAgentsWithPing)
 	out.UpsertedAgents = upsertedAgents
 	for i, ws := range update.DeletedWorkspaces {
 		out.DeletedWorkspaces[i] = &Workspace{
@@ -466,7 +501,7 @@ func (u *updater) createPeerUpdateLocked(update tailnet.WorkspaceUpdate) *PeerUp
 
 // convertAgentsLocked takes a list of `tailnet.Agent` and converts them to proto agents.
 // If there is an active connection, the last handshake time is populated.
-func (u *updater) convertAgentsLocked(agents []*tailnet.Agent) []*Agent {
+func (u *updater) convertAgentsLocked(agents []*agentWithPing) []*Agent {
 	out := make([]*Agent, 0, len(agents))
 
 	for _, agent := range agents {
@@ -477,12 +512,26 @@ func (u *updater) convertAgentsLocked(agents []*tailnet.Agent) []*Agent {
 		sort.Slice(fqdn, func(i, j int) bool {
 			return len(fqdn[i]) < len(fqdn[j])
 		})
+		var lastPing *LastPing
+		if agent.lastPing != nil {
+			var preferredDerpLatency *durationpb.Duration
+			if agent.lastPing.preferredDerpLatency != nil {
+				preferredDerpLatency = durationpb.New(*agent.lastPing.preferredDerpLatency)
+			}
+			lastPing = &LastPing{
+				Latency:              durationpb.New(agent.lastPing.pingDur),
+				DidP2P:               agent.lastPing.didP2p,
+				PreferredDerp:        agent.lastPing.preferredDerp,
+				PreferredDerpLatency: preferredDerpLatency,
+			}
+		}
 		protoAgent := &Agent{
 			Id:          tailnet.UUIDToByteSlice(agent.ID),
 			Name:        agent.Name,
 			WorkspaceId: tailnet.UUIDToByteSlice(agent.WorkspaceID),
 			Fqdn:        fqdn,
 			IpAddrs:     hostsToIPStrings(agent.Hosts),
+			LastPing:    lastPing,
 		}
 		if u.conn != nil {
 			diags := u.conn.GetPeerDiagnostics(agent.ID)
@@ -514,8 +563,8 @@ func (u *updater) stop() error {
 		return nil
 	}
 	err := u.conn.Close()
-	u.conn = nil
 	u.cancel()
+	u.conn = nil
 	return err
 }
 
@@ -525,7 +574,7 @@ func (u *updater) sendAgentUpdate() {
 	u.mu.Lock()
 	defer u.mu.Unlock()
 
-	agents := make([]*tailnet.Agent, 0, len(u.agents))
+	agents := make([]*agentWithPing, 0, len(u.agents))
 	for _, agent := range u.agents {
 		agents = append(agents, &agent)
 	}
@@ -558,17 +607,85 @@ func (u *updater) netStatusLoop() {
 		case <-u.ctx.Done():
 			return
 		case <-ticker.C:
+			u.recordLatencies()
 			u.sendAgentUpdate()
 		}
 	}
 }
 
+func (u *updater) recordLatencies() {
+	var agentsIDsToPing []uuid.UUID
+	u.mu.Lock()
+	for _, agent := range u.agents {
+		agentsIDsToPing = append(agentsIDsToPing, agent.ID)
+	}
+	conn := u.conn
+	u.mu.Unlock()
+
+	if conn == nil {
+		u.logger.Debug(u.ctx, "skipping pings as tunnel is not connected")
+		return
+	}
+
+	go func() {
+		// We need a waitgroup to cancel the context after all pings are done.
+		var wg sync.WaitGroup
+		pingCtx, cancelFunc := context.WithTimeout(u.ctx, netStatusInterval)
+		defer cancelFunc()
+		for _, agentID := range agentsIDsToPing {
+			wg.Add(1)
+			go func() {
+				defer wg.Done()
+
+				pingDur, didP2p, pingResult, err := conn.Ping(pingCtx, agentID)
+				if err != nil {
+					u.logger.Warn(u.ctx, "failed to ping agent", slog.F("agent_id", agentID), slog.Error(err))
+					return
+				}
+
+				// We fetch the Node and DERPMap after each ping, as it may have
+				// changed.
+				node := conn.Node()
+				derpMap := conn.DERPMap()
+				if node == nil || derpMap == nil {
+					u.logger.Warn(u.ctx, "failed to get DERP map or node after ping")
+					return
+				}
+				derpLatencies := tailnet.ExtractDERPLatency(node, derpMap)
+				preferredDerp := tailnet.ExtractPreferredDERPName(pingResult, node, derpMap)
+				var preferredDerpLatency *time.Duration
+				if derpLatency, ok := derpLatencies[preferredDerp]; ok {
+					preferredDerpLatency = &derpLatency
+				} else {
+					u.logger.Debug(u.ctx, "preferred DERP not found in DERP latency map", slog.F("preferred_derp", preferredDerp))
+				}
+
+				// Write back results
+				u.mu.Lock()
+				defer u.mu.Unlock()
+				if agent, ok := u.agents[agentID]; ok {
+					agent.lastPing = &lastPing{
+						pingDur:              pingDur,
+						didP2p:               didP2p,
+						preferredDerp:        preferredDerp,
+						preferredDerpLatency: preferredDerpLatency,
+					}
+					u.agents[agentID] = agent
+				} else {
+					u.logger.Debug(u.ctx, "ignoring ping result for unknown agent", slog.F("agent_id", agentID))
+				}
+			}()
+		}
+		wg.Wait()
+	}()
+}
+
 // processSnapshotUpdate handles the logic when a full state update is received.
 // When the tunnel is live, we only receive diffs, but the first packet on any given
 // reconnect to the tailnet API is a full state.
 // Without this logic we weren't processing deletes for any workspaces or agents deleted
 // while the client was disconnected while the computer was asleep.
-func processSnapshotUpdate(update *tailnet.WorkspaceUpdate, agents map[uuid.UUID]tailnet.Agent, workspaces map[uuid.UUID]tailnet.Workspace) {
+func processSnapshotUpdate(update *tailnet.WorkspaceUpdate, agents map[uuid.UUID]agentWithPing, workspaces map[uuid.UUID]tailnet.Workspace) {
 	// ignoredWorkspaces is initially populated with the workspaces that are
 	// in the current update. Later on we populate it with the deleted workspaces too
 	// so that we don't send duplicate updates. Same applies to ignoredAgents.
diff --git a/vpn/tunnel_internal_test.go b/vpn/tunnel_internal_test.go
index 15eb9cf569f5e..5c4e6ec03d47f 100644
--- a/vpn/tunnel_internal_test.go
+++ b/vpn/tunnel_internal_test.go
@@ -15,10 +15,13 @@ import (
 	"github.com/google/uuid"
 	"github.com/stretchr/testify/require"
 	"google.golang.org/protobuf/types/known/timestamppb"
+	"tailscale.com/ipn/ipnstate"
+	"tailscale.com/tailcfg"
 	"tailscale.com/util/dnsname"
 
 	"github.com/coder/quartz"
 
+	maputil "github.com/coder/coder/v2/coderd/util/maps"
 	"github.com/coder/coder/v2/tailnet"
 	"github.com/coder/coder/v2/tailnet/proto"
 	"github.com/coder/coder/v2/testutil"
@@ -57,15 +60,59 @@ func newFakeConn(state tailnet.WorkspaceUpdate, hsTime time.Time) *fakeConn {
 	}
 }
 
+func (f *fakeConn) withManualPings() *fakeConn {
+	f.returnPing = make(chan struct{})
+	return f
+}
+
 type fakeConn struct {
-	state   tailnet.WorkspaceUpdate
-	hsTime  time.Time
-	closed  chan struct{}
-	doClose sync.Once
+	state      tailnet.WorkspaceUpdate
+	returnPing chan struct{}
+	hsTime     time.Time
+	closed     chan struct{}
+	doClose    sync.Once
+}
+
+func (*fakeConn) DERPMap() *tailcfg.DERPMap {
+	return &tailcfg.DERPMap{
+		Regions: map[int]*tailcfg.DERPRegion{
+			999: {
+				RegionID:   999,
+				RegionCode: "zzz",
+				RegionName: "Coder Region",
+			},
+		},
+	}
+}
+
+func (*fakeConn) Node() *tailnet.Node {
+	return &tailnet.Node{
+		PreferredDERP: 999,
+		DERPLatency: map[string]float64{
+			"999": 0.1,
+		},
+	}
 }
 
 var _ Conn = (*fakeConn)(nil)
 
+func (f *fakeConn) Ping(ctx context.Context, agentID uuid.UUID) (time.Duration, bool, *ipnstate.PingResult, error) {
+	if f.returnPing == nil {
+		return time.Millisecond * 100, true, &ipnstate.PingResult{
+			DERPRegionID: 999,
+		}, nil
+	}
+
+	select {
+	case <-ctx.Done():
+		return 0, false, nil, ctx.Err()
+	case <-f.returnPing:
+		return time.Millisecond * 100, true, &ipnstate.PingResult{
+			DERPRegionID: 999,
+		}, nil
+	}
+}
+
 func (f *fakeConn) CurrentWorkspaceState() (tailnet.WorkspaceUpdate, error) {
 	return f.state, nil
 }
@@ -292,7 +339,7 @@ func TestUpdater_createPeerUpdate(t *testing.T) {
 	updater := updater{
 		ctx:         ctx,
 		netLoopDone: make(chan struct{}),
-		agents:      map[uuid.UUID]tailnet.Agent{},
+		agents:      map[uuid.UUID]agentWithPing{},
 		workspaces:  map[uuid.UUID]tailnet.Workspace{},
 		conn:        newFakeConn(tailnet.WorkspaceUpdate{}, hsTime),
 	}
@@ -430,6 +477,22 @@ func TestTunnel_sendAgentUpdate(t *testing.T) {
 		require.Equal(t, hsTime, req.msg.GetPeerUpdate().UpsertedAgents[0].LastHandshake.AsTime())
 	}
 
+	// Latency is gathered in the background, so it'll eventually be sent
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		mClock.AdvanceNext()
+		req = testutil.TryReceive(ctx, t, mgr.requests)
+		if len(req.msg.GetPeerUpdate().UpsertedAgents) == 0 {
+			return false
+		}
+		if req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing == nil {
+			return false
+		}
+		if req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.Latency.AsDuration().Milliseconds() != 100 {
+			return false
+		}
+		return req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.PreferredDerp == "Coder Region"
+	}, testutil.IntervalFast)
+
 	// Upsert a new agent
 	err = tun.Update(tailnet.WorkspaceUpdate{
 		UpsertedWorkspaces: []*tailnet.Workspace{},
@@ -459,6 +522,10 @@ func TestTunnel_sendAgentUpdate(t *testing.T) {
 
 	require.Equal(t, aID1[:], req.msg.GetPeerUpdate().UpsertedAgents[0].Id)
 	require.Equal(t, hsTime, req.msg.GetPeerUpdate().UpsertedAgents[0].LastHandshake.AsTime())
+	// The latency of the first agent is still set
+	require.NotNil(t, req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing)
+	require.EqualValues(t, 100, req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.Latency.AsDuration().Milliseconds())
+
 	require.Equal(t, aID2[:], req.msg.GetPeerUpdate().UpsertedAgents[1].Id)
 	require.Equal(t, hsTime, req.msg.GetPeerUpdate().UpsertedAgents[1].LastHandshake.AsTime())
 
@@ -486,6 +553,22 @@ func TestTunnel_sendAgentUpdate(t *testing.T) {
 	require.Len(t, req.msg.GetPeerUpdate().UpsertedAgents, 1)
 	require.Equal(t, aID2[:], req.msg.GetPeerUpdate().UpsertedAgents[0].Id)
 	require.Equal(t, hsTime, req.msg.GetPeerUpdate().UpsertedAgents[0].LastHandshake.AsTime())
+
+	// Eventually the second agent's latency is set
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		mClock.AdvanceNext()
+		req = testutil.TryReceive(ctx, t, mgr.requests)
+		if len(req.msg.GetPeerUpdate().UpsertedAgents) == 0 {
+			return false
+		}
+		if req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing == nil {
+			return false
+		}
+		if req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.Latency.AsDuration().Milliseconds() != 100 {
+			return false
+		}
+		return req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.PreferredDerp == "Coder Region"
+	}, testutil.IntervalFast)
 }
 
 func TestTunnel_sendAgentUpdateReconnect(t *testing.T) {
@@ -693,6 +776,178 @@ func TestTunnel_sendAgentUpdateWorkspaceReconnect(t *testing.T) {
 	require.Equal(t, wID1[:], peerUpdate.DeletedWorkspaces[0].Id)
 }
 
+func TestTunnel_slowPing(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+
+	mClock := quartz.NewMock(t)
+
+	wID1 := uuid.UUID{1}
+	aID1 := uuid.UUID{2}
+	hsTime := time.Now().Add(-time.Minute).UTC()
+
+	client := newFakeClient(ctx, t)
+	conn := newFakeConn(tailnet.WorkspaceUpdate{}, hsTime).withManualPings()
+
+	tun, mgr := setupTunnel(t, ctx, client, mClock)
+	errCh := make(chan error, 1)
+	var resp *TunnelMessage
+	go func() {
+		r, err := mgr.unaryRPC(ctx, &ManagerMessage{
+			Msg: &ManagerMessage_Start{
+				Start: &StartRequest{
+					TunnelFileDescriptor: 2,
+					CoderUrl:             "https://coder.example.com",
+					ApiToken:             "fakeToken",
+				},
+			},
+		})
+		resp = r
+		errCh <- err
+	}()
+	testutil.RequireSend(ctx, t, client.ch, conn)
+	err := testutil.TryReceive(ctx, t, errCh)
+	require.NoError(t, err)
+	_, ok := resp.Msg.(*TunnelMessage_Start)
+	require.True(t, ok)
+
+	// Inform the tunnel of the initial state
+	err = tun.Update(tailnet.WorkspaceUpdate{
+		UpsertedWorkspaces: []*tailnet.Workspace{
+			{
+				ID: wID1, Name: "w1", Status: proto.Workspace_STARTING,
+			},
+		},
+		UpsertedAgents: []*tailnet.Agent{
+			{
+				ID:          aID1,
+				Name:        "agent1",
+				WorkspaceID: wID1,
+				Hosts: map[dnsname.FQDN][]netip.Addr{
+					"agent1.coder.": {netip.MustParseAddr("fd60:627a:a42b:0101::")},
+				},
+			},
+		},
+	})
+	require.NoError(t, err)
+	req := testutil.TryReceive(ctx, t, mgr.requests)
+	require.Nil(t, req.msg.Rpc)
+	require.NotNil(t, req.msg.GetPeerUpdate())
+	require.Len(t, req.msg.GetPeerUpdate().UpsertedAgents, 1)
+	require.Equal(t, aID1[:], req.msg.GetPeerUpdate().UpsertedAgents[0].Id)
+
+	// We can't check that it *never* pings, so the best we can do is
+	// check it doesn't ping even with 5 goroutines attempting to,
+	// and that updates are received as normal
+	for range 5 {
+		mClock.AdvanceNext()
+		require.Nil(t, req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing)
+	}
+
+	// Provided that it hasn't been 5 seconds since the last AdvanceNext call,
+	// there'll be a ping in-flight that will return with this message
+	testutil.RequireSend(ctx, t, conn.returnPing, struct{}{})
+	// Which will mean we'll eventually receive a PeerUpdate with the ping
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		mClock.AdvanceNext()
+		req = testutil.TryReceive(ctx, t, mgr.requests)
+		if len(req.msg.GetPeerUpdate().UpsertedAgents) == 0 {
+			return false
+		}
+		if req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing == nil {
+			return false
+		}
+		if req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.Latency.AsDuration().Milliseconds() != 100 {
+			return false
+		}
+		return req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing.PreferredDerp == "Coder Region"
+	}, testutil.IntervalFast)
+}
+
+func TestTunnel_stopMidPing(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+
+	mClock := quartz.NewMock(t)
+
+	wID1 := uuid.UUID{1}
+	aID1 := uuid.UUID{2}
+	hsTime := time.Now().Add(-time.Minute).UTC()
+
+	client := newFakeClient(ctx, t)
+	conn := newFakeConn(tailnet.WorkspaceUpdate{}, hsTime).withManualPings()
+
+	tun, mgr := setupTunnel(t, ctx, client, mClock)
+	errCh := make(chan error, 1)
+	var resp *TunnelMessage
+	go func() {
+		r, err := mgr.unaryRPC(ctx, &ManagerMessage{
+			Msg: &ManagerMessage_Start{
+				Start: &StartRequest{
+					TunnelFileDescriptor: 2,
+					CoderUrl:             "https://coder.example.com",
+					ApiToken:             "fakeToken",
+				},
+			},
+		})
+		resp = r
+		errCh <- err
+	}()
+	testutil.RequireSend(ctx, t, client.ch, conn)
+	err := testutil.TryReceive(ctx, t, errCh)
+	require.NoError(t, err)
+	_, ok := resp.Msg.(*TunnelMessage_Start)
+	require.True(t, ok)
+
+	// Inform the tunnel of the initial state
+	err = tun.Update(tailnet.WorkspaceUpdate{
+		UpsertedWorkspaces: []*tailnet.Workspace{
+			{
+				ID: wID1, Name: "w1", Status: proto.Workspace_STARTING,
+			},
+		},
+		UpsertedAgents: []*tailnet.Agent{
+			{
+				ID:          aID1,
+				Name:        "agent1",
+				WorkspaceID: wID1,
+				Hosts: map[dnsname.FQDN][]netip.Addr{
+					"agent1.coder.": {netip.MustParseAddr("fd60:627a:a42b:0101::")},
+				},
+			},
+		},
+	})
+	require.NoError(t, err)
+	req := testutil.TryReceive(ctx, t, mgr.requests)
+	require.Nil(t, req.msg.Rpc)
+	require.NotNil(t, req.msg.GetPeerUpdate())
+	require.Len(t, req.msg.GetPeerUpdate().UpsertedAgents, 1)
+	require.Equal(t, aID1[:], req.msg.GetPeerUpdate().UpsertedAgents[0].Id)
+
+	// We'll have some pings in flight when we stop
+	for range 5 {
+		mClock.AdvanceNext()
+		req = testutil.TryReceive(ctx, t, mgr.requests)
+		require.Nil(t, req.msg.GetPeerUpdate().UpsertedAgents[0].LastPing)
+	}
+
+	// Stop the tunnel
+	go func() {
+		r, err := mgr.unaryRPC(ctx, &ManagerMessage{
+			Msg: &ManagerMessage_Stop{},
+		})
+		resp = r
+		errCh <- err
+	}()
+	testutil.TryReceive(ctx, t, conn.closed)
+	err = testutil.TryReceive(ctx, t, errCh)
+	require.NoError(t, err)
+	_, ok = resp.Msg.(*TunnelMessage_Stop)
+	require.True(t, ok)
+}
+
 //nolint:revive // t takes precedence
 func setupTunnel(t *testing.T, ctx context.Context, client *fakeClient, mClock *quartz.Mock) (*Tunnel, *speaker[*ManagerMessage, *TunnelMessage, TunnelMessage]) {
 	mp, tp := net.Pipe()
@@ -902,11 +1157,13 @@ func TestProcessFreshState(t *testing.T) {
 		t.Run(tt.name, func(t *testing.T) {
 			t.Parallel()
 
-			agentsCopy := make(map[uuid.UUID]tailnet.Agent)
-			maps.Copy(agentsCopy, tt.initialAgents)
-
-			workspaceCopy := make(map[uuid.UUID]tailnet.Workspace)
-			maps.Copy(workspaceCopy, tt.initialWorkspaces)
+			agentsCopy := maputil.Map(tt.initialAgents, func(a tailnet.Agent) agentWithPing {
+				return agentWithPing{
+					Agent:    a.Clone(),
+					lastPing: nil,
+				}
+			})
+			workspaceCopy := maps.Clone(tt.initialWorkspaces)
 
 			processSnapshotUpdate(tt.update, agentsCopy, workspaceCopy)
 
diff --git a/vpn/version.go b/vpn/version.go
index 91aac9175f748..2bf815e903e29 100644
--- a/vpn/version.go
+++ b/vpn/version.go
@@ -16,7 +16,14 @@ var CurrentSupportedVersions = RPCVersionList{
 		// - device_id: Coder Desktop device ID
 		// - device_os: Coder Desktop OS information
 		// - coder_desktop_version: Coder Desktop version
-		{Major: 1, Minor: 1},
+		// 1.2 adds network related information to Agent:
+		// - last_ping:
+		//   - latency: RTT of the most recently sent ping
+		//   - did_p2p: Whether the last ping was sent over P2P
+		//   - preferred_derp: The server that DERP relayed connections are
+		//                     using, if they're not using P2P.
+		//   - preferred_derp_latency: The latency to the preferred DERP
+		{Major: 1, Minor: 2},
 	},
 }
 
diff --git a/vpn/vpn.pb.go b/vpn/vpn.pb.go
index c89d3e51e6c92..bc5829d763dfd 100644
--- a/vpn/vpn.pb.go
+++ b/vpn/vpn.pb.go
@@ -9,6 +9,7 @@ package vpn
 import (
 	protoreflect "google.golang.org/protobuf/reflect/protoreflect"
 	protoimpl "google.golang.org/protobuf/runtime/protoimpl"
+	durationpb "google.golang.org/protobuf/types/known/durationpb"
 	timestamppb "google.golang.org/protobuf/types/known/timestamppb"
 	reflect "reflect"
 	sync "sync"
@@ -205,7 +206,7 @@ func (x Status_Lifecycle) Number() protoreflect.EnumNumber {
 
 // Deprecated: Use Status_Lifecycle.Descriptor instead.
 func (Status_Lifecycle) EnumDescriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{17, 0}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{18, 0}
 }
 
 // RPC allows a very simple unary request/response RPC mechanism.  The requester generates a unique
@@ -986,6 +987,8 @@ type Agent struct {
 	// last_handshake is the primary indicator of whether we are connected to a peer. Zero value or
 	// anything longer than 5 minutes ago means there is a problem.
 	LastHandshake *timestamppb.Timestamp `protobuf:"bytes,6,opt,name=last_handshake,json=lastHandshake,proto3" json:"last_handshake,omitempty"`
+	// If unset, a successful ping has not yet been made.
+	LastPing *LastPing `protobuf:"bytes,7,opt,name=last_ping,json=lastPing,proto3,oneof" json:"last_ping,omitempty"`
 }
 
 func (x *Agent) Reset() {
@@ -1062,6 +1065,90 @@ func (x *Agent) GetLastHandshake() *timestamppb.Timestamp {
 	return nil
 }
 
+func (x *Agent) GetLastPing() *LastPing {
+	if x != nil {
+		return x.LastPing
+	}
+	return nil
+}
+
+type LastPing struct {
+	state         protoimpl.MessageState
+	sizeCache     protoimpl.SizeCache
+	unknownFields protoimpl.UnknownFields
+
+	// latency is the RTT of the ping to the agent.
+	Latency *durationpb.Duration `protobuf:"bytes,1,opt,name=latency,proto3" json:"latency,omitempty"`
+	// did_p2p indicates whether the ping was sent P2P, or over DERP.
+	DidP2P bool `protobuf:"varint,2,opt,name=did_p2p,json=didP2p,proto3" json:"did_p2p,omitempty"`
+	// preferred_derp is the human readable name of the preferred DERP region,
+	// or the region used for the last ping, if it was sent over DERP.
+	PreferredDerp string `protobuf:"bytes,3,opt,name=preferred_derp,json=preferredDerp,proto3" json:"preferred_derp,omitempty"`
+	// preferred_derp_latency is the last known latency to the preferred DERP
+	// region. Unset if the region does not appear in the DERP map.
+	PreferredDerpLatency *durationpb.Duration `protobuf:"bytes,4,opt,name=preferred_derp_latency,json=preferredDerpLatency,proto3,oneof" json:"preferred_derp_latency,omitempty"`
+}
+
+func (x *LastPing) Reset() {
+	*x = LastPing{}
+	if protoimpl.UnsafeEnabled {
+		mi := &file_vpn_vpn_proto_msgTypes[10]
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		ms.StoreMessageInfo(mi)
+	}
+}
+
+func (x *LastPing) String() string {
+	return protoimpl.X.MessageStringOf(x)
+}
+
+func (*LastPing) ProtoMessage() {}
+
+func (x *LastPing) ProtoReflect() protoreflect.Message {
+	mi := &file_vpn_vpn_proto_msgTypes[10]
+	if protoimpl.UnsafeEnabled && x != nil {
+		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
+		if ms.LoadMessageInfo() == nil {
+			ms.StoreMessageInfo(mi)
+		}
+		return ms
+	}
+	return mi.MessageOf(x)
+}
+
+// Deprecated: Use LastPing.ProtoReflect.Descriptor instead.
+func (*LastPing) Descriptor() ([]byte, []int) {
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{10}
+}
+
+func (x *LastPing) GetLatency() *durationpb.Duration {
+	if x != nil {
+		return x.Latency
+	}
+	return nil
+}
+
+func (x *LastPing) GetDidP2P() bool {
+	if x != nil {
+		return x.DidP2P
+	}
+	return false
+}
+
+func (x *LastPing) GetPreferredDerp() string {
+	if x != nil {
+		return x.PreferredDerp
+	}
+	return ""
+}
+
+func (x *LastPing) GetPreferredDerpLatency() *durationpb.Duration {
+	if x != nil {
+		return x.PreferredDerpLatency
+	}
+	return nil
+}
+
 // NetworkSettingsRequest is based on
 // https://developer.apple.com/documentation/networkextension/nepackettunnelnetworksettings for
 // macOS.  It is a request/response message with response NetworkSettingsResponse
@@ -1081,7 +1168,7 @@ type NetworkSettingsRequest struct {
 func (x *NetworkSettingsRequest) Reset() {
 	*x = NetworkSettingsRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[10]
+		mi := &file_vpn_vpn_proto_msgTypes[11]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1094,7 +1181,7 @@ func (x *NetworkSettingsRequest) String() string {
 func (*NetworkSettingsRequest) ProtoMessage() {}
 
 func (x *NetworkSettingsRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[10]
+	mi := &file_vpn_vpn_proto_msgTypes[11]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1107,7 +1194,7 @@ func (x *NetworkSettingsRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use NetworkSettingsRequest.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsRequest) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{10}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{11}
 }
 
 func (x *NetworkSettingsRequest) GetTunnelOverheadBytes() uint32 {
@@ -1166,7 +1253,7 @@ type NetworkSettingsResponse struct {
 func (x *NetworkSettingsResponse) Reset() {
 	*x = NetworkSettingsResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[11]
+		mi := &file_vpn_vpn_proto_msgTypes[12]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1179,7 +1266,7 @@ func (x *NetworkSettingsResponse) String() string {
 func (*NetworkSettingsResponse) ProtoMessage() {}
 
 func (x *NetworkSettingsResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[11]
+	mi := &file_vpn_vpn_proto_msgTypes[12]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1192,7 +1279,7 @@ func (x *NetworkSettingsResponse) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use NetworkSettingsResponse.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsResponse) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{11}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{12}
 }
 
 func (x *NetworkSettingsResponse) GetSuccess() bool {
@@ -1231,7 +1318,7 @@ type StartRequest struct {
 func (x *StartRequest) Reset() {
 	*x = StartRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[12]
+		mi := &file_vpn_vpn_proto_msgTypes[13]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1244,7 +1331,7 @@ func (x *StartRequest) String() string {
 func (*StartRequest) ProtoMessage() {}
 
 func (x *StartRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[12]
+	mi := &file_vpn_vpn_proto_msgTypes[13]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1257,7 +1344,7 @@ func (x *StartRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use StartRequest.ProtoReflect.Descriptor instead.
 func (*StartRequest) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{12}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{13}
 }
 
 func (x *StartRequest) GetTunnelFileDescriptor() int32 {
@@ -1321,7 +1408,7 @@ type StartResponse struct {
 func (x *StartResponse) Reset() {
 	*x = StartResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[13]
+		mi := &file_vpn_vpn_proto_msgTypes[14]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1334,7 +1421,7 @@ func (x *StartResponse) String() string {
 func (*StartResponse) ProtoMessage() {}
 
 func (x *StartResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[13]
+	mi := &file_vpn_vpn_proto_msgTypes[14]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1347,7 +1434,7 @@ func (x *StartResponse) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use StartResponse.ProtoReflect.Descriptor instead.
 func (*StartResponse) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{13}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{14}
 }
 
 func (x *StartResponse) GetSuccess() bool {
@@ -1375,7 +1462,7 @@ type StopRequest struct {
 func (x *StopRequest) Reset() {
 	*x = StopRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[14]
+		mi := &file_vpn_vpn_proto_msgTypes[15]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1388,7 +1475,7 @@ func (x *StopRequest) String() string {
 func (*StopRequest) ProtoMessage() {}
 
 func (x *StopRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[14]
+	mi := &file_vpn_vpn_proto_msgTypes[15]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1401,7 +1488,7 @@ func (x *StopRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use StopRequest.ProtoReflect.Descriptor instead.
 func (*StopRequest) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{14}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{15}
 }
 
 // StopResponse is a response to stopping the tunnel. After sending this response, the tunnel closes
@@ -1418,7 +1505,7 @@ type StopResponse struct {
 func (x *StopResponse) Reset() {
 	*x = StopResponse{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[15]
+		mi := &file_vpn_vpn_proto_msgTypes[16]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1431,7 +1518,7 @@ func (x *StopResponse) String() string {
 func (*StopResponse) ProtoMessage() {}
 
 func (x *StopResponse) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[15]
+	mi := &file_vpn_vpn_proto_msgTypes[16]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1444,7 +1531,7 @@ func (x *StopResponse) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use StopResponse.ProtoReflect.Descriptor instead.
 func (*StopResponse) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{15}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{16}
 }
 
 func (x *StopResponse) GetSuccess() bool {
@@ -1472,7 +1559,7 @@ type StatusRequest struct {
 func (x *StatusRequest) Reset() {
 	*x = StatusRequest{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[16]
+		mi := &file_vpn_vpn_proto_msgTypes[17]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1485,7 +1572,7 @@ func (x *StatusRequest) String() string {
 func (*StatusRequest) ProtoMessage() {}
 
 func (x *StatusRequest) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[16]
+	mi := &file_vpn_vpn_proto_msgTypes[17]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1498,7 +1585,7 @@ func (x *StatusRequest) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use StatusRequest.ProtoReflect.Descriptor instead.
 func (*StatusRequest) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{16}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{17}
 }
 
 // Status is sent in response to a StatusRequest or broadcasted to all clients
@@ -1519,7 +1606,7 @@ type Status struct {
 func (x *Status) Reset() {
 	*x = Status{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[17]
+		mi := &file_vpn_vpn_proto_msgTypes[18]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1532,7 +1619,7 @@ func (x *Status) String() string {
 func (*Status) ProtoMessage() {}
 
 func (x *Status) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[17]
+	mi := &file_vpn_vpn_proto_msgTypes[18]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1545,7 +1632,7 @@ func (x *Status) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use Status.ProtoReflect.Descriptor instead.
 func (*Status) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{17}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{18}
 }
 
 func (x *Status) GetLifecycle() Status_Lifecycle {
@@ -1581,7 +1668,7 @@ type Log_Field struct {
 func (x *Log_Field) Reset() {
 	*x = Log_Field{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[18]
+		mi := &file_vpn_vpn_proto_msgTypes[19]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1594,7 +1681,7 @@ func (x *Log_Field) String() string {
 func (*Log_Field) ProtoMessage() {}
 
 func (x *Log_Field) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[18]
+	mi := &file_vpn_vpn_proto_msgTypes[19]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1642,7 +1729,7 @@ type NetworkSettingsRequest_DNSSettings struct {
 func (x *NetworkSettingsRequest_DNSSettings) Reset() {
 	*x = NetworkSettingsRequest_DNSSettings{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[19]
+		mi := &file_vpn_vpn_proto_msgTypes[20]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1655,7 +1742,7 @@ func (x *NetworkSettingsRequest_DNSSettings) String() string {
 func (*NetworkSettingsRequest_DNSSettings) ProtoMessage() {}
 
 func (x *NetworkSettingsRequest_DNSSettings) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[19]
+	mi := &file_vpn_vpn_proto_msgTypes[20]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1668,7 +1755,7 @@ func (x *NetworkSettingsRequest_DNSSettings) ProtoReflect() protoreflect.Message
 
 // Deprecated: Use NetworkSettingsRequest_DNSSettings.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsRequest_DNSSettings) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{10, 0}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{11, 0}
 }
 
 func (x *NetworkSettingsRequest_DNSSettings) GetServers() []string {
@@ -1722,7 +1809,7 @@ type NetworkSettingsRequest_IPv4Settings struct {
 func (x *NetworkSettingsRequest_IPv4Settings) Reset() {
 	*x = NetworkSettingsRequest_IPv4Settings{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[20]
+		mi := &file_vpn_vpn_proto_msgTypes[21]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1735,7 +1822,7 @@ func (x *NetworkSettingsRequest_IPv4Settings) String() string {
 func (*NetworkSettingsRequest_IPv4Settings) ProtoMessage() {}
 
 func (x *NetworkSettingsRequest_IPv4Settings) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[20]
+	mi := &file_vpn_vpn_proto_msgTypes[21]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1748,7 +1835,7 @@ func (x *NetworkSettingsRequest_IPv4Settings) ProtoReflect() protoreflect.Messag
 
 // Deprecated: Use NetworkSettingsRequest_IPv4Settings.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsRequest_IPv4Settings) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{10, 1}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{11, 1}
 }
 
 func (x *NetworkSettingsRequest_IPv4Settings) GetAddrs() []string {
@@ -1800,7 +1887,7 @@ type NetworkSettingsRequest_IPv6Settings struct {
 func (x *NetworkSettingsRequest_IPv6Settings) Reset() {
 	*x = NetworkSettingsRequest_IPv6Settings{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[21]
+		mi := &file_vpn_vpn_proto_msgTypes[22]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1813,7 +1900,7 @@ func (x *NetworkSettingsRequest_IPv6Settings) String() string {
 func (*NetworkSettingsRequest_IPv6Settings) ProtoMessage() {}
 
 func (x *NetworkSettingsRequest_IPv6Settings) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[21]
+	mi := &file_vpn_vpn_proto_msgTypes[22]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1826,7 +1913,7 @@ func (x *NetworkSettingsRequest_IPv6Settings) ProtoReflect() protoreflect.Messag
 
 // Deprecated: Use NetworkSettingsRequest_IPv6Settings.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsRequest_IPv6Settings) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{10, 2}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{11, 2}
 }
 
 func (x *NetworkSettingsRequest_IPv6Settings) GetAddrs() []string {
@@ -1871,7 +1958,7 @@ type NetworkSettingsRequest_IPv4Settings_IPv4Route struct {
 func (x *NetworkSettingsRequest_IPv4Settings_IPv4Route) Reset() {
 	*x = NetworkSettingsRequest_IPv4Settings_IPv4Route{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[22]
+		mi := &file_vpn_vpn_proto_msgTypes[23]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1884,7 +1971,7 @@ func (x *NetworkSettingsRequest_IPv4Settings_IPv4Route) String() string {
 func (*NetworkSettingsRequest_IPv4Settings_IPv4Route) ProtoMessage() {}
 
 func (x *NetworkSettingsRequest_IPv4Settings_IPv4Route) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[22]
+	mi := &file_vpn_vpn_proto_msgTypes[23]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1897,7 +1984,7 @@ func (x *NetworkSettingsRequest_IPv4Settings_IPv4Route) ProtoReflect() protorefl
 
 // Deprecated: Use NetworkSettingsRequest_IPv4Settings_IPv4Route.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsRequest_IPv4Settings_IPv4Route) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{10, 1, 0}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{11, 1, 0}
 }
 
 func (x *NetworkSettingsRequest_IPv4Settings_IPv4Route) GetDestination() string {
@@ -1935,7 +2022,7 @@ type NetworkSettingsRequest_IPv6Settings_IPv6Route struct {
 func (x *NetworkSettingsRequest_IPv6Settings_IPv6Route) Reset() {
 	*x = NetworkSettingsRequest_IPv6Settings_IPv6Route{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[23]
+		mi := &file_vpn_vpn_proto_msgTypes[24]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -1948,7 +2035,7 @@ func (x *NetworkSettingsRequest_IPv6Settings_IPv6Route) String() string {
 func (*NetworkSettingsRequest_IPv6Settings_IPv6Route) ProtoMessage() {}
 
 func (x *NetworkSettingsRequest_IPv6Settings_IPv6Route) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[23]
+	mi := &file_vpn_vpn_proto_msgTypes[24]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -1961,7 +2048,7 @@ func (x *NetworkSettingsRequest_IPv6Settings_IPv6Route) ProtoReflect() protorefl
 
 // Deprecated: Use NetworkSettingsRequest_IPv6Settings_IPv6Route.ProtoReflect.Descriptor instead.
 func (*NetworkSettingsRequest_IPv6Settings_IPv6Route) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{10, 2, 0}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{11, 2, 0}
 }
 
 func (x *NetworkSettingsRequest_IPv6Settings_IPv6Route) GetDestination() string {
@@ -1998,7 +2085,7 @@ type StartRequest_Header struct {
 func (x *StartRequest_Header) Reset() {
 	*x = StartRequest_Header{}
 	if protoimpl.UnsafeEnabled {
-		mi := &file_vpn_vpn_proto_msgTypes[24]
+		mi := &file_vpn_vpn_proto_msgTypes[25]
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		ms.StoreMessageInfo(mi)
 	}
@@ -2011,7 +2098,7 @@ func (x *StartRequest_Header) String() string {
 func (*StartRequest_Header) ProtoMessage() {}
 
 func (x *StartRequest_Header) ProtoReflect() protoreflect.Message {
-	mi := &file_vpn_vpn_proto_msgTypes[24]
+	mi := &file_vpn_vpn_proto_msgTypes[25]
 	if protoimpl.UnsafeEnabled && x != nil {
 		ms := protoimpl.X.MessageStateOf(protoimpl.Pointer(x))
 		if ms.LoadMessageInfo() == nil {
@@ -2024,7 +2111,7 @@ func (x *StartRequest_Header) ProtoReflect() protoreflect.Message {
 
 // Deprecated: Use StartRequest_Header.ProtoReflect.Descriptor instead.
 func (*StartRequest_Header) Descriptor() ([]byte, []int) {
-	return file_vpn_vpn_proto_rawDescGZIP(), []int{12, 0}
+	return file_vpn_vpn_proto_rawDescGZIP(), []int{13, 0}
 }
 
 func (x *StartRequest_Header) GetName() string {
@@ -2047,6 +2134,8 @@ var file_vpn_vpn_proto_rawDesc = []byte{
 	0x0a, 0x0d, 0x76, 0x70, 0x6e, 0x2f, 0x76, 0x70, 0x6e, 0x2e, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x12,
 	0x03, 0x76, 0x70, 0x6e, 0x1a, 0x1f, 0x67, 0x6f, 0x6f, 0x67, 0x6c, 0x65, 0x2f, 0x70, 0x72, 0x6f,
 	0x74, 0x6f, 0x62, 0x75, 0x66, 0x2f, 0x74, 0x69, 0x6d, 0x65, 0x73, 0x74, 0x61, 0x6d, 0x70, 0x2e,
+	0x70, 0x72, 0x6f, 0x74, 0x6f, 0x1a, 0x1e, 0x67, 0x6f, 0x6f, 0x67, 0x6c, 0x65, 0x2f, 0x70, 0x72,
+	0x6f, 0x74, 0x6f, 0x62, 0x75, 0x66, 0x2f, 0x64, 0x75, 0x72, 0x61, 0x74, 0x69, 0x6f, 0x6e, 0x2e,
 	0x70, 0x72, 0x6f, 0x74, 0x6f, 0x22, 0x3d, 0x0a, 0x03, 0x52, 0x50, 0x43, 0x12, 0x15, 0x0a, 0x06,
 	0x6d, 0x73, 0x67, 0x5f, 0x69, 0x64, 0x18, 0x01, 0x20, 0x01, 0x28, 0x04, 0x52, 0x05, 0x6d, 0x73,
 	0x67, 0x49, 0x64, 0x12, 0x1f, 0x0a, 0x0b, 0x72, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x5f,
@@ -2158,7 +2247,7 @@ var file_vpn_vpn_proto_rawDesc = []byte{
 	0x49, 0x4c, 0x45, 0x44, 0x10, 0x06, 0x12, 0x0d, 0x0a, 0x09, 0x43, 0x41, 0x4e, 0x43, 0x45, 0x4c,
 	0x49, 0x4e, 0x47, 0x10, 0x07, 0x12, 0x0c, 0x0a, 0x08, 0x43, 0x41, 0x4e, 0x43, 0x45, 0x4c, 0x45,
 	0x44, 0x10, 0x08, 0x12, 0x0c, 0x0a, 0x08, 0x44, 0x45, 0x4c, 0x45, 0x54, 0x49, 0x4e, 0x47, 0x10,
-	0x09, 0x12, 0x0b, 0x0a, 0x07, 0x44, 0x45, 0x4c, 0x45, 0x54, 0x45, 0x44, 0x10, 0x0a, 0x22, 0xc0,
+	0x09, 0x12, 0x0b, 0x0a, 0x07, 0x44, 0x45, 0x4c, 0x45, 0x54, 0x45, 0x44, 0x10, 0x0a, 0x22, 0xff,
 	0x01, 0x0a, 0x05, 0x41, 0x67, 0x65, 0x6e, 0x74, 0x12, 0x0e, 0x0a, 0x02, 0x69, 0x64, 0x18, 0x01,
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 	0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x04, 0x6e, 0x61, 0x6d, 0x65, 0x12, 0x21, 0x0a, 0x0c,
@@ -2171,148 +2260,167 @@ var file_vpn_vpn_proto_rawDesc = []byte{
 	0x18, 0x06, 0x20, 0x01, 0x28, 0x0b, 0x32, 0x1a, 0x2e, 0x67, 0x6f, 0x6f, 0x67, 0x6c, 0x65, 0x2e,
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 }
 
 var (
@@ -2328,7 +2436,7 @@ func file_vpn_vpn_proto_rawDescGZIP() []byte {
 }
 
 var file_vpn_vpn_proto_enumTypes = make([]protoimpl.EnumInfo, 3)
-var file_vpn_vpn_proto_msgTypes = make([]protoimpl.MessageInfo, 25)
+var file_vpn_vpn_proto_msgTypes = make([]protoimpl.MessageInfo, 26)
 var file_vpn_vpn_proto_goTypes = []interface{}{
 	(Log_Level)(0),                              // 0: vpn.Log.Level
 	(Workspace_Status)(0),                       // 1: vpn.Workspace.Status
@@ -2343,66 +2451,71 @@ var file_vpn_vpn_proto_goTypes = []interface{}{
 	(*PeerUpdate)(nil),                          // 10: vpn.PeerUpdate
 	(*Workspace)(nil),                           // 11: vpn.Workspace
 	(*Agent)(nil),                               // 12: vpn.Agent
-	(*NetworkSettingsRequest)(nil),              // 13: vpn.NetworkSettingsRequest
-	(*NetworkSettingsResponse)(nil),             // 14: vpn.NetworkSettingsResponse
-	(*StartRequest)(nil),                        // 15: vpn.StartRequest
-	(*StartResponse)(nil),                       // 16: vpn.StartResponse
-	(*StopRequest)(nil),                         // 17: vpn.StopRequest
-	(*StopResponse)(nil),                        // 18: vpn.StopResponse
-	(*StatusRequest)(nil),                       // 19: vpn.StatusRequest
-	(*Status)(nil),                              // 20: vpn.Status
-	(*Log_Field)(nil),                           // 21: vpn.Log.Field
-	(*NetworkSettingsRequest_DNSSettings)(nil),  // 22: vpn.NetworkSettingsRequest.DNSSettings
-	(*NetworkSettingsRequest_IPv4Settings)(nil), // 23: vpn.NetworkSettingsRequest.IPv4Settings
-	(*NetworkSettingsRequest_IPv6Settings)(nil), // 24: vpn.NetworkSettingsRequest.IPv6Settings
-	(*NetworkSettingsRequest_IPv4Settings_IPv4Route)(nil), // 25: vpn.NetworkSettingsRequest.IPv4Settings.IPv4Route
-	(*NetworkSettingsRequest_IPv6Settings_IPv6Route)(nil), // 26: vpn.NetworkSettingsRequest.IPv6Settings.IPv6Route
-	(*StartRequest_Header)(nil),                           // 27: vpn.StartRequest.Header
-	(*timestamppb.Timestamp)(nil),                         // 28: google.protobuf.Timestamp
+	(*LastPing)(nil),                            // 13: vpn.LastPing
+	(*NetworkSettingsRequest)(nil),              // 14: vpn.NetworkSettingsRequest
+	(*NetworkSettingsResponse)(nil),             // 15: vpn.NetworkSettingsResponse
+	(*StartRequest)(nil),                        // 16: vpn.StartRequest
+	(*StartResponse)(nil),                       // 17: vpn.StartResponse
+	(*StopRequest)(nil),                         // 18: vpn.StopRequest
+	(*StopResponse)(nil),                        // 19: vpn.StopResponse
+	(*StatusRequest)(nil),                       // 20: vpn.StatusRequest
+	(*Status)(nil),                              // 21: vpn.Status
+	(*Log_Field)(nil),                           // 22: vpn.Log.Field
+	(*NetworkSettingsRequest_DNSSettings)(nil),  // 23: vpn.NetworkSettingsRequest.DNSSettings
+	(*NetworkSettingsRequest_IPv4Settings)(nil), // 24: vpn.NetworkSettingsRequest.IPv4Settings
+	(*NetworkSettingsRequest_IPv6Settings)(nil), // 25: vpn.NetworkSettingsRequest.IPv6Settings
+	(*NetworkSettingsRequest_IPv4Settings_IPv4Route)(nil), // 26: vpn.NetworkSettingsRequest.IPv4Settings.IPv4Route
+	(*NetworkSettingsRequest_IPv6Settings_IPv6Route)(nil), // 27: vpn.NetworkSettingsRequest.IPv6Settings.IPv6Route
+	(*StartRequest_Header)(nil),                           // 28: vpn.StartRequest.Header
+	(*timestamppb.Timestamp)(nil),                         // 29: google.protobuf.Timestamp
+	(*durationpb.Duration)(nil),                           // 30: google.protobuf.Duration
 }
 var file_vpn_vpn_proto_depIdxs = []int32{
 	3,  // 0: vpn.ManagerMessage.rpc:type_name -> vpn.RPC
 	9,  // 1: vpn.ManagerMessage.get_peer_update:type_name -> vpn.GetPeerUpdate
-	14, // 2: vpn.ManagerMessage.network_settings:type_name -> vpn.NetworkSettingsResponse
-	15, // 3: vpn.ManagerMessage.start:type_name -> vpn.StartRequest
-	17, // 4: vpn.ManagerMessage.stop:type_name -> vpn.StopRequest
+	15, // 2: vpn.ManagerMessage.network_settings:type_name -> vpn.NetworkSettingsResponse
+	16, // 3: vpn.ManagerMessage.start:type_name -> vpn.StartRequest
+	18, // 4: vpn.ManagerMessage.stop:type_name -> vpn.StopRequest
 	3,  // 5: vpn.TunnelMessage.rpc:type_name -> vpn.RPC
 	8,  // 6: vpn.TunnelMessage.log:type_name -> vpn.Log
 	10, // 7: vpn.TunnelMessage.peer_update:type_name -> vpn.PeerUpdate
-	13, // 8: vpn.TunnelMessage.network_settings:type_name -> vpn.NetworkSettingsRequest
-	16, // 9: vpn.TunnelMessage.start:type_name -> vpn.StartResponse
-	18, // 10: vpn.TunnelMessage.stop:type_name -> vpn.StopResponse
+	14, // 8: vpn.TunnelMessage.network_settings:type_name -> vpn.NetworkSettingsRequest
+	17, // 9: vpn.TunnelMessage.start:type_name -> vpn.StartResponse
+	19, // 10: vpn.TunnelMessage.stop:type_name -> vpn.StopResponse
 	3,  // 11: vpn.ClientMessage.rpc:type_name -> vpn.RPC
-	15, // 12: vpn.ClientMessage.start:type_name -> vpn.StartRequest
-	17, // 13: vpn.ClientMessage.stop:type_name -> vpn.StopRequest
-	19, // 14: vpn.ClientMessage.status:type_name -> vpn.StatusRequest
+	16, // 12: vpn.ClientMessage.start:type_name -> vpn.StartRequest
+	18, // 13: vpn.ClientMessage.stop:type_name -> vpn.StopRequest
+	20, // 14: vpn.ClientMessage.status:type_name -> vpn.StatusRequest
 	3,  // 15: vpn.ServiceMessage.rpc:type_name -> vpn.RPC
-	16, // 16: vpn.ServiceMessage.start:type_name -> vpn.StartResponse
-	18, // 17: vpn.ServiceMessage.stop:type_name -> vpn.StopResponse
-	20, // 18: vpn.ServiceMessage.status:type_name -> vpn.Status
+	17, // 16: vpn.ServiceMessage.start:type_name -> vpn.StartResponse
+	19, // 17: vpn.ServiceMessage.stop:type_name -> vpn.StopResponse
+	21, // 18: vpn.ServiceMessage.status:type_name -> vpn.Status
 	0,  // 19: vpn.Log.level:type_name -> vpn.Log.Level
-	21, // 20: vpn.Log.fields:type_name -> vpn.Log.Field
+	22, // 20: vpn.Log.fields:type_name -> vpn.Log.Field
 	11, // 21: vpn.PeerUpdate.upserted_workspaces:type_name -> vpn.Workspace
 	12, // 22: vpn.PeerUpdate.upserted_agents:type_name -> vpn.Agent
 	11, // 23: vpn.PeerUpdate.deleted_workspaces:type_name -> vpn.Workspace
 	12, // 24: vpn.PeerUpdate.deleted_agents:type_name -> vpn.Agent
 	1,  // 25: vpn.Workspace.status:type_name -> vpn.Workspace.Status
-	28, // 26: vpn.Agent.last_handshake:type_name -> google.protobuf.Timestamp
-	22, // 27: vpn.NetworkSettingsRequest.dns_settings:type_name -> vpn.NetworkSettingsRequest.DNSSettings
-	23, // 28: vpn.NetworkSettingsRequest.ipv4_settings:type_name -> vpn.NetworkSettingsRequest.IPv4Settings
-	24, // 29: vpn.NetworkSettingsRequest.ipv6_settings:type_name -> vpn.NetworkSettingsRequest.IPv6Settings
-	27, // 30: vpn.StartRequest.headers:type_name -> vpn.StartRequest.Header
-	2,  // 31: vpn.Status.lifecycle:type_name -> vpn.Status.Lifecycle
-	10, // 32: vpn.Status.peer_update:type_name -> vpn.PeerUpdate
-	25, // 33: vpn.NetworkSettingsRequest.IPv4Settings.included_routes:type_name -> vpn.NetworkSettingsRequest.IPv4Settings.IPv4Route
-	25, // 34: vpn.NetworkSettingsRequest.IPv4Settings.excluded_routes:type_name -> vpn.NetworkSettingsRequest.IPv4Settings.IPv4Route
-	26, // 35: vpn.NetworkSettingsRequest.IPv6Settings.included_routes:type_name -> vpn.NetworkSettingsRequest.IPv6Settings.IPv6Route
-	26, // 36: vpn.NetworkSettingsRequest.IPv6Settings.excluded_routes:type_name -> vpn.NetworkSettingsRequest.IPv6Settings.IPv6Route
-	37, // [37:37] is the sub-list for method output_type
-	37, // [37:37] is the sub-list for method input_type
-	37, // [37:37] is the sub-list for extension type_name
-	37, // [37:37] is the sub-list for extension extendee
-	0,  // [0:37] is the sub-list for field type_name
+	29, // 26: vpn.Agent.last_handshake:type_name -> google.protobuf.Timestamp
+	13, // 27: vpn.Agent.last_ping:type_name -> vpn.LastPing
+	30, // 28: vpn.LastPing.latency:type_name -> google.protobuf.Duration
+	30, // 29: vpn.LastPing.preferred_derp_latency:type_name -> google.protobuf.Duration
+	23, // 30: vpn.NetworkSettingsRequest.dns_settings:type_name -> vpn.NetworkSettingsRequest.DNSSettings
+	24, // 31: vpn.NetworkSettingsRequest.ipv4_settings:type_name -> vpn.NetworkSettingsRequest.IPv4Settings
+	25, // 32: vpn.NetworkSettingsRequest.ipv6_settings:type_name -> vpn.NetworkSettingsRequest.IPv6Settings
+	28, // 33: vpn.StartRequest.headers:type_name -> vpn.StartRequest.Header
+	2,  // 34: vpn.Status.lifecycle:type_name -> vpn.Status.Lifecycle
+	10, // 35: vpn.Status.peer_update:type_name -> vpn.PeerUpdate
+	26, // 36: vpn.NetworkSettingsRequest.IPv4Settings.included_routes:type_name -> vpn.NetworkSettingsRequest.IPv4Settings.IPv4Route
+	26, // 37: vpn.NetworkSettingsRequest.IPv4Settings.excluded_routes:type_name -> vpn.NetworkSettingsRequest.IPv4Settings.IPv4Route
+	27, // 38: vpn.NetworkSettingsRequest.IPv6Settings.included_routes:type_name -> vpn.NetworkSettingsRequest.IPv6Settings.IPv6Route
+	27, // 39: vpn.NetworkSettingsRequest.IPv6Settings.excluded_routes:type_name -> vpn.NetworkSettingsRequest.IPv6Settings.IPv6Route
+	40, // [40:40] is the sub-list for method output_type
+	40, // [40:40] is the sub-list for method input_type
+	40, // [40:40] is the sub-list for extension type_name
+	40, // [40:40] is the sub-list for extension extendee
+	0,  // [0:40] is the sub-list for field type_name
 }
 
 func init() { file_vpn_vpn_proto_init() }
@@ -2532,7 +2645,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[10].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsRequest); i {
+			switch v := v.(*LastPing); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2544,7 +2657,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[11].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsResponse); i {
+			switch v := v.(*NetworkSettingsRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2556,7 +2669,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[12].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*StartRequest); i {
+			switch v := v.(*NetworkSettingsResponse); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2568,7 +2681,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[13].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*StartResponse); i {
+			switch v := v.(*StartRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2580,7 +2693,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[14].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*StopRequest); i {
+			switch v := v.(*StartResponse); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2592,7 +2705,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[15].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*StopResponse); i {
+			switch v := v.(*StopRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2604,7 +2717,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[16].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*StatusRequest); i {
+			switch v := v.(*StopResponse); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2616,7 +2729,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[17].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*Status); i {
+			switch v := v.(*StatusRequest); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2628,7 +2741,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[18].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*Log_Field); i {
+			switch v := v.(*Status); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2640,7 +2753,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[19].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsRequest_DNSSettings); i {
+			switch v := v.(*Log_Field); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2652,7 +2765,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[20].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsRequest_IPv4Settings); i {
+			switch v := v.(*NetworkSettingsRequest_DNSSettings); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2664,7 +2777,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[21].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsRequest_IPv6Settings); i {
+			switch v := v.(*NetworkSettingsRequest_IPv4Settings); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2676,7 +2789,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[22].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsRequest_IPv4Settings_IPv4Route); i {
+			switch v := v.(*NetworkSettingsRequest_IPv6Settings); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2688,7 +2801,7 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[23].Exporter = func(v interface{}, i int) interface{} {
-			switch v := v.(*NetworkSettingsRequest_IPv6Settings_IPv6Route); i {
+			switch v := v.(*NetworkSettingsRequest_IPv4Settings_IPv4Route); i {
 			case 0:
 				return &v.state
 			case 1:
@@ -2700,6 +2813,18 @@ func file_vpn_vpn_proto_init() {
 			}
 		}
 		file_vpn_vpn_proto_msgTypes[24].Exporter = func(v interface{}, i int) interface{} {
+			switch v := v.(*NetworkSettingsRequest_IPv6Settings_IPv6Route); i {
+			case 0:
+				return &v.state
+			case 1:
+				return &v.sizeCache
+			case 2:
+				return &v.unknownFields
+			default:
+				return nil
+			}
+		}
+		file_vpn_vpn_proto_msgTypes[25].Exporter = func(v interface{}, i int) interface{} {
 			switch v := v.(*StartRequest_Header); i {
 			case 0:
 				return &v.state
@@ -2735,13 +2860,15 @@ func file_vpn_vpn_proto_init() {
 		(*ServiceMessage_Stop)(nil),
 		(*ServiceMessage_Status)(nil),
 	}
+	file_vpn_vpn_proto_msgTypes[9].OneofWrappers = []interface{}{}
+	file_vpn_vpn_proto_msgTypes[10].OneofWrappers = []interface{}{}
 	type x struct{}
 	out := protoimpl.TypeBuilder{
 		File: protoimpl.DescBuilder{
 			GoPackagePath: reflect.TypeOf(x{}).PkgPath(),
 			RawDescriptor: file_vpn_vpn_proto_rawDesc,
 			NumEnums:      3,
-			NumMessages:   25,
+			NumMessages:   26,
 			NumExtensions: 0,
 			NumServices:   0,
 		},
diff --git a/vpn/vpn.proto b/vpn/vpn.proto
index 963098c60a648..44383fa80e0cb 100644
--- a/vpn/vpn.proto
+++ b/vpn/vpn.proto
@@ -3,6 +3,7 @@ option go_package = "github.com/coder/coder/v2/vpn";
 option csharp_namespace = "Coder.Desktop.Vpn.Proto";
 
 import "google/protobuf/timestamp.proto";
+import "google/protobuf/duration.proto";
 
 package vpn;
 
@@ -130,6 +131,21 @@ message Agent {
 	// last_handshake is the primary indicator of whether we are connected to a peer. Zero value or
 	// anything longer than 5 minutes ago means there is a problem.
 	google.protobuf.Timestamp last_handshake = 6;
+	// If unset, a successful ping has not yet been made.
+	optional LastPing last_ping = 7;
+}
+
+message LastPing {
+	// latency is the RTT of the ping to the agent.
+	google.protobuf.Duration latency = 1;
+	// did_p2p indicates whether the ping was sent P2P, or over DERP.
+	bool did_p2p = 2;
+	// preferred_derp is the human readable name of the preferred DERP region,
+	// or the region used for the last ping, if it was sent over DERP.
+	string preferred_derp = 3;
+	// preferred_derp_latency is the last known latency to the preferred DERP
+	// region. Unset if the region does not appear in the DERP map.
+	optional google.protobuf.Duration preferred_derp_latency = 4;
 }
 
 // NetworkSettingsRequest is based on