diff --git a/coderd/workspaceagents.go b/coderd/workspaceagents.go
index a06cf96ea8616..b8b71b330275b 100644
--- a/coderd/workspaceagents.go
+++ b/coderd/workspaceagents.go
@@ -1652,6 +1652,8 @@ func (api *API) tailnetRPCConn(rw http.ResponseWriter, r *http.Request) {
 		DeviceOS:            nil,
 		CoderDesktopVersion: nil,
 	}
+
+	fillCoderDesktopTelemetry(r, &connectionTelemetryEvent, api.Logger)
 	api.Telemetry.Report(&telemetry.Snapshot{
 		UserTailnetConnections: []telemetry.UserTailnetConnection{connectionTelemetryEvent},
 	})
@@ -1681,6 +1683,34 @@ func (api *API) tailnetRPCConn(rw http.ResponseWriter, r *http.Request) {
 	}
 }
 
+// fillCoderDesktopTelemetry fills out the provided event based on a Coder Desktop telemetry header on the request, if
+// present.
+func fillCoderDesktopTelemetry(r *http.Request, event *telemetry.UserTailnetConnection, logger slog.Logger) {
+	// Parse desktop telemetry from header if it exists
+	desktopTelemetryHeader := r.Header.Get(codersdk.CoderDesktopTelemetryHeader)
+	if desktopTelemetryHeader != "" {
+		var telemetryData codersdk.CoderDesktopTelemetry
+		if err := telemetryData.FromHeader(desktopTelemetryHeader); err == nil {
+			// Only set fields if they aren't empty
+			if telemetryData.DeviceID != "" {
+				event.DeviceID = &telemetryData.DeviceID
+			}
+			if telemetryData.DeviceOS != "" {
+				event.DeviceOS = &telemetryData.DeviceOS
+			}
+			if telemetryData.CoderDesktopVersion != "" {
+				event.CoderDesktopVersion = &telemetryData.CoderDesktopVersion
+			}
+			logger.Debug(r.Context(), "received desktop telemetry",
+				slog.F("device_id", telemetryData.DeviceID),
+				slog.F("device_os", telemetryData.DeviceOS),
+				slog.F("desktop_version", telemetryData.CoderDesktopVersion))
+		} else {
+			logger.Warn(r.Context(), "failed to parse desktop telemetry header", slog.Error(err))
+		}
+	}
+}
+
 // createExternalAuthResponse creates an ExternalAuthResponse based on the
 // provider type. This is to support legacy `/workspaceagents/me/gitauth`
 // which uses `Username` and `Password`.
diff --git a/coderd/workspaceagents_test.go b/coderd/workspaceagents_test.go
index 899708ce1fb06..c4519f731b203 100644
--- a/coderd/workspaceagents_test.go
+++ b/coderd/workspaceagents_test.go
@@ -51,6 +51,7 @@ import (
 	"github.com/coder/coder/v2/coderd/jwtutils"
 	"github.com/coder/coder/v2/coderd/rbac"
 	"github.com/coder/coder/v2/coderd/telemetry"
+	"github.com/coder/coder/v2/coderd/util/ptr"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/agentsdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
@@ -2135,12 +2136,8 @@ func TestOwnedWorkspacesCoordinate(t *testing.T) {
 
 	ctx := testutil.Context(t, testutil.WaitLong)
 	logger := testutil.Logger(t)
-
-	fTelemetry := newFakeTelemetryReporter(ctx, t, 200)
-	fTelemetry.enabled = false
 	firstClient, _, api := coderdtest.NewWithAPI(t, &coderdtest.Options{
-		Coordinator:       tailnet.NewCoordinator(logger),
-		TelemetryReporter: fTelemetry,
+		Coordinator: tailnet.NewCoordinator(logger),
 	})
 	firstUser := coderdtest.CreateFirstUser(t, firstClient)
 	member, memberUser := coderdtest.CreateAnotherUser(t, firstClient, firstUser.OrganizationID, rbac.RoleTemplateAdmin())
@@ -2148,17 +2145,12 @@ func TestOwnedWorkspacesCoordinate(t *testing.T) {
 	// Create a workspace with an agent
 	firstWorkspace := buildWorkspaceWithAgent(t, member, firstUser.OrganizationID, memberUser.ID, api.Database, api.Pubsub)
 
-	// enable telemetry now that workspace is built; we don't care about snapshots before this.
-	fTelemetry.enabled = true
-
 	u, err := member.URL.Parse("/api/v2/tailnet")
 	require.NoError(t, err)
 	q := u.Query()
 	q.Set("version", "2.0")
 	u.RawQuery = q.Encode()
 
-	predialTime := time.Now()
-
 	//nolint:bodyclose // websocket package closes this for you
 	wsConn, resp, err := websocket.Dial(ctx, u.String(), &websocket.DialOptions{
 		HTTPHeader: http.Header{
@@ -2173,15 +2165,6 @@ func TestOwnedWorkspacesCoordinate(t *testing.T) {
 	}
 	defer wsConn.Close(websocket.StatusNormalClosure, "done")
 
-	// Check telemetry
-	snapshot := testutil.RequireRecvCtx(ctx, t, fTelemetry.snapshots)
-	require.Len(t, snapshot.UserTailnetConnections, 1)
-	telemetryConnection := snapshot.UserTailnetConnections[0]
-	require.Equal(t, memberUser.ID.String(), telemetryConnection.UserID)
-	require.GreaterOrEqual(t, telemetryConnection.ConnectedAt, predialTime)
-	require.LessOrEqual(t, telemetryConnection.ConnectedAt, time.Now())
-	require.NotEmpty(t, telemetryConnection.PeerID)
-
 	rpcClient, err := tailnet.NewDRPCClient(
 		websocket.NetConn(ctx, wsConn, websocket.MessageBinary),
 		logger,
@@ -2229,23 +2212,135 @@ func TestOwnedWorkspacesCoordinate(t *testing.T) {
 			NumAgents: 0,
 		},
 	})
-	err = stream.Close()
-	require.NoError(t, err)
+}
 
-	beforeDisconnectTime := time.Now()
-	err = wsConn.Close(websocket.StatusNormalClosure, "done")
+func TestUserTailnetTelemetry(t *testing.T) {
+	t.Parallel()
+
+	telemetryData := &codersdk.CoderDesktopTelemetry{
+		DeviceOS:            "Windows",
+		DeviceID:            "device001",
+		CoderDesktopVersion: "0.22.1",
+	}
+	fullHeader, err := json.Marshal(telemetryData)
 	require.NoError(t, err)
 
-	snapshot = testutil.RequireRecvCtx(ctx, t, fTelemetry.snapshots)
-	require.Len(t, snapshot.UserTailnetConnections, 1)
-	telemetryDisconnection := snapshot.UserTailnetConnections[0]
-	require.Equal(t, memberUser.ID.String(), telemetryDisconnection.UserID)
-	require.Equal(t, telemetryConnection.ConnectedAt, telemetryDisconnection.ConnectedAt)
-	require.Equal(t, telemetryConnection.UserID, telemetryDisconnection.UserID)
-	require.Equal(t, telemetryConnection.PeerID, telemetryDisconnection.PeerID)
-	require.NotNil(t, telemetryDisconnection.DisconnectedAt)
-	require.GreaterOrEqual(t, *telemetryDisconnection.DisconnectedAt, beforeDisconnectTime)
-	require.LessOrEqual(t, *telemetryDisconnection.DisconnectedAt, time.Now())
+	testCases := []struct {
+		name    string
+		headers map[string]string
+		// only used for DeviceID, DeviceOS, CoderDesktopVersion
+		expected telemetry.UserTailnetConnection
+	}{
+		{
+			name:     "no header",
+			headers:  map[string]string{},
+			expected: telemetry.UserTailnetConnection{},
+		},
+		{
+			name: "full header",
+			headers: map[string]string{
+				codersdk.CoderDesktopTelemetryHeader: string(fullHeader),
+			},
+			expected: telemetry.UserTailnetConnection{
+				DeviceOS:            ptr.Ref("Windows"),
+				DeviceID:            ptr.Ref("device001"),
+				CoderDesktopVersion: ptr.Ref("0.22.1"),
+			},
+		},
+		{
+			name: "empty header",
+			headers: map[string]string{
+				codersdk.CoderDesktopTelemetryHeader: "",
+			},
+			expected: telemetry.UserTailnetConnection{},
+		},
+		{
+			name: "invalid header",
+			headers: map[string]string{
+				codersdk.CoderDesktopTelemetryHeader: "{\"device_os",
+			},
+			expected: telemetry.UserTailnetConnection{},
+		},
+	}
+
+	// nolint: paralleltest // no longer need to reinitialize loop vars in go 1.22
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			ctx := testutil.Context(t, testutil.WaitLong)
+			logger := testutil.Logger(t)
+
+			fTelemetry := newFakeTelemetryReporter(ctx, t, 200)
+			fTelemetry.enabled = false
+			firstClient := coderdtest.New(t, &coderdtest.Options{
+				Logger:            &logger,
+				TelemetryReporter: fTelemetry,
+			})
+			firstUser := coderdtest.CreateFirstUser(t, firstClient)
+			member, memberUser := coderdtest.CreateAnotherUser(t, firstClient, firstUser.OrganizationID, rbac.RoleTemplateAdmin())
+
+			headers := http.Header{
+				"Coder-Session-Token": []string{member.SessionToken()},
+			}
+			for k, v := range tc.headers {
+				headers.Add(k, v)
+			}
+
+			// enable telemetry now that user is created.
+			fTelemetry.enabled = true
+
+			u, err := member.URL.Parse("/api/v2/tailnet")
+			require.NoError(t, err)
+			q := u.Query()
+			q.Set("version", "2.0")
+			u.RawQuery = q.Encode()
+
+			predialTime := time.Now()
+
+			//nolint:bodyclose // websocket package closes this for you
+			wsConn, resp, err := websocket.Dial(ctx, u.String(), &websocket.DialOptions{
+				HTTPHeader: headers,
+			})
+			if err != nil {
+				if resp != nil && resp.StatusCode != http.StatusSwitchingProtocols {
+					err = codersdk.ReadBodyAsError(resp)
+				}
+				require.NoError(t, err)
+			}
+			defer wsConn.Close(websocket.StatusNormalClosure, "done")
+
+			// Check telemetry
+			snapshot := testutil.RequireRecvCtx(ctx, t, fTelemetry.snapshots)
+			require.Len(t, snapshot.UserTailnetConnections, 1)
+			telemetryConnection := snapshot.UserTailnetConnections[0]
+			require.Equal(t, memberUser.ID.String(), telemetryConnection.UserID)
+			require.GreaterOrEqual(t, telemetryConnection.ConnectedAt, predialTime)
+			require.LessOrEqual(t, telemetryConnection.ConnectedAt, time.Now())
+			require.NotEmpty(t, telemetryConnection.PeerID)
+			requireEqualOrBothNil(t, telemetryConnection.DeviceID, tc.expected.DeviceID)
+			requireEqualOrBothNil(t, telemetryConnection.DeviceOS, tc.expected.DeviceOS)
+			requireEqualOrBothNil(t, telemetryConnection.CoderDesktopVersion, tc.expected.CoderDesktopVersion)
+
+			beforeDisconnectTime := time.Now()
+			err = wsConn.Close(websocket.StatusNormalClosure, "done")
+			require.NoError(t, err)
+
+			snapshot = testutil.RequireRecvCtx(ctx, t, fTelemetry.snapshots)
+			require.Len(t, snapshot.UserTailnetConnections, 1)
+			telemetryDisconnection := snapshot.UserTailnetConnections[0]
+			require.Equal(t, memberUser.ID.String(), telemetryDisconnection.UserID)
+			require.Equal(t, telemetryConnection.ConnectedAt, telemetryDisconnection.ConnectedAt)
+			require.Equal(t, telemetryConnection.UserID, telemetryDisconnection.UserID)
+			require.Equal(t, telemetryConnection.PeerID, telemetryDisconnection.PeerID)
+			require.NotNil(t, telemetryDisconnection.DisconnectedAt)
+			require.GreaterOrEqual(t, *telemetryDisconnection.DisconnectedAt, beforeDisconnectTime)
+			require.LessOrEqual(t, *telemetryDisconnection.DisconnectedAt, time.Now())
+			requireEqualOrBothNil(t, telemetryConnection.DeviceID, tc.expected.DeviceID)
+			requireEqualOrBothNil(t, telemetryConnection.DeviceOS, tc.expected.DeviceOS)
+			requireEqualOrBothNil(t, telemetryConnection.CoderDesktopVersion, tc.expected.CoderDesktopVersion)
+		})
+	}
 }
 
 func buildWorkspaceWithAgent(
@@ -2414,3 +2509,12 @@ func (f *fakeTelemetryReporter) Enabled() bool {
 
 // Close implements the telemetry.Reporter interface.
 func (*fakeTelemetryReporter) Close() {}
+
+func requireEqualOrBothNil[T any](t testing.TB, a, b *T) {
+	t.Helper()
+	if a != nil && b != nil {
+		require.Equal(t, *a, *b)
+		return
+	}
+	require.Equal(t, a, b)
+}
diff --git a/codersdk/client.go b/codersdk/client.go
index d267355d37096..8a341ee742a76 100644
--- a/codersdk/client.go
+++ b/codersdk/client.go
@@ -76,6 +76,10 @@ const (
 	// only.
 	CLITelemetryHeader = "Coder-CLI-Telemetry"
 
+	// CoderDesktopTelemetryHeader contains a JSON-encoded representation of Desktop telemetry
+	// fields, including device ID, OS, and Desktop version.
+	CoderDesktopTelemetryHeader = "Coder-Desktop-Telemetry"
+
 	// ProvisionerDaemonPSK contains the authentication pre-shared key for an external provisioner daemon
 	ProvisionerDaemonPSK = "Coder-Provisioner-Daemon-PSK"
 
@@ -523,6 +527,28 @@ func (e ValidationError) Error() string {
 
 var _ error = (*ValidationError)(nil)
 
+// CoderDesktopTelemetry represents the telemetry data sent from Coder Desktop clients.
+// @typescript-ignore CoderDesktopTelemetry
+type CoderDesktopTelemetry struct {
+	DeviceID            string `json:"device_id"`
+	DeviceOS            string `json:"device_os"`
+	CoderDesktopVersion string `json:"coder_desktop_version"`
+}
+
+// FromHeader parses the desktop telemetry from the provided header value.
+// Returns nil if the header is empty or if parsing fails.
+func (t *CoderDesktopTelemetry) FromHeader(headerValue string) error {
+	if headerValue == "" {
+		return nil
+	}
+	return json.Unmarshal([]byte(headerValue), t)
+}
+
+// IsEmpty returns true if all fields in the telemetry data are empty.
+func (t *CoderDesktopTelemetry) IsEmpty() bool {
+	return t.DeviceID == "" && t.DeviceOS == "" && t.CoderDesktopVersion == ""
+}
+
 // IsConnectionError is a convenience function for checking if the source of an
 // error is due to a 'connection refused', 'no such host', etc.
 func IsConnectionError(err error) bool {
diff --git a/codersdk/client_internal_test.go b/codersdk/client_internal_test.go
index 9093c277783fa..0650c3c32097d 100644
--- a/codersdk/client_internal_test.go
+++ b/codersdk/client_internal_test.go
@@ -27,6 +27,7 @@ import (
 
 	"cdr.dev/slog"
 	"cdr.dev/slog/sloggers/sloghuman"
+
 	"github.com/coder/coder/v2/testutil"
 )
 
diff --git a/site/src/api/typesGenerated.ts b/site/src/api/typesGenerated.ts
index 1e9b471ad46f4..01ed0c919a835 100644
--- a/site/src/api/typesGenerated.ts
+++ b/site/src/api/typesGenerated.ts
@@ -290,6 +290,9 @@ export interface ChangePasswordWithOneTimePasscodeRequest {
 	readonly one_time_passcode: string;
 }
 
+// From codersdk/client.go
+export const CoderDesktopTelemetryHeader = "Coder-Desktop-Telemetry";
+
 // From codersdk/insights.go
 export interface ConnectionLatency {
 	readonly p50: number;
diff --git a/vpn/speaker_internal_test.go b/vpn/speaker_internal_test.go
index 5985043307107..9ec795bc033b8 100644
--- a/vpn/speaker_internal_test.go
+++ b/vpn/speaker_internal_test.go
@@ -15,6 +15,7 @@ import (
 
 	"cdr.dev/slog"
 	"cdr.dev/slog/sloggers/slogtest"
+
 	"github.com/coder/coder/v2/testutil"
 )
 
@@ -47,7 +48,7 @@ func TestSpeaker_RawPeer(t *testing.T) {
 		errCh <- err
 	}()
 
-	expectedHandshake := "codervpn tunnel 1.0\n"
+	expectedHandshake := "codervpn tunnel 1.1\n"
 
 	b := make([]byte, 256)
 	n, err := mp.Read(b)
@@ -155,7 +156,7 @@ func TestSpeaker_OversizeHandshake(t *testing.T) {
 		errCh <- err
 	}()
 
-	expectedHandshake := "codervpn tunnel 1.0\n"
+	expectedHandshake := "codervpn tunnel 1.1\n"
 
 	b := make([]byte, 256)
 	n, err := mp.Read(b)
@@ -177,12 +178,12 @@ func TestSpeaker_HandshakeInvalid(t *testing.T) {
 	for _, tc := range []struct {
 		name, handshake string
 	}{
-		{name: "preamble", handshake: "ssh manager 1.0\n"},
+		{name: "preamble", handshake: "ssh manager 1.1\n"},
 		{name: "2components", handshake: "ssh manager\n"},
 		{name: "newmajors", handshake: "codervpn manager 2.0,3.0\n"},
 		{name: "0version", handshake: "codervpn 0.1 manager\n"},
-		{name: "unknown_role", handshake: "codervpn 1.0 supervisor\n"},
-		{name: "unexpected_role", handshake: "codervpn 1.0 tunnel\n"},
+		{name: "unknown_role", handshake: "codervpn 1.1 supervisor\n"},
+		{name: "unexpected_role", handshake: "codervpn 1.1 tunnel\n"},
 	} {
 		t.Run(tc.name, func(t *testing.T) {
 			t.Parallel()
@@ -208,7 +209,7 @@ func TestSpeaker_HandshakeInvalid(t *testing.T) {
 			_, err = mp.Write([]byte(tc.handshake))
 			require.NoError(t, err)
 
-			expectedHandshake := "codervpn tunnel 1.0\n"
+			expectedHandshake := "codervpn tunnel 1.1\n"
 			b := make([]byte, 256)
 			n, err := mp.Read(b)
 			require.NoError(t, err)
@@ -246,7 +247,7 @@ func TestSpeaker_CorruptMessage(t *testing.T) {
 		errCh <- err
 	}()
 
-	expectedHandshake := "codervpn tunnel 1.0\n"
+	expectedHandshake := "codervpn tunnel 1.1\n"
 
 	b := make([]byte, 256)
 	n, err := mp.Read(b)
diff --git a/vpn/tunnel.go b/vpn/tunnel.go
index e40732ae10e38..611e7189f4e75 100644
--- a/vpn/tunnel.go
+++ b/vpn/tunnel.go
@@ -26,8 +26,10 @@ import (
 	"tailscale.com/wgengine/router"
 
 	"cdr.dev/slog"
-	"github.com/coder/coder/v2/tailnet"
 	"github.com/coder/quartz"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/tailnet"
 )
 
 // netStatusInterval is the interval at which the tunnel sends network status updates to the manager.
@@ -236,6 +238,24 @@ func (t *Tunnel) start(req *StartRequest) error {
 	for _, h := range req.GetHeaders() {
 		header.Add(h.GetName(), h.GetValue())
 	}
+
+	// Add desktop telemetry if any fields are provided
+	telemetryData := codersdk.CoderDesktopTelemetry{
+		DeviceID:            req.GetDeviceId(),
+		DeviceOS:            req.GetDeviceOs(),
+		CoderDesktopVersion: req.GetCoderDesktopVersion(),
+	}
+	if !telemetryData.IsEmpty() {
+		headerValue, err := json.Marshal(telemetryData)
+		if err == nil {
+			header.Set(codersdk.CoderDesktopTelemetryHeader, string(headerValue))
+			t.logger.Debug(t.ctx, "added desktop telemetry header",
+				slog.F("data", telemetryData))
+		} else {
+			t.logger.Warn(t.ctx, "failed to marshal telemetry data")
+		}
+	}
+
 	var networkingStack NetworkStack
 	if t.networkingStackFn != nil {
 		networkingStack, err = t.networkingStackFn(t, req, t.clientLogger)
diff --git a/vpn/tunnel_internal_test.go b/vpn/tunnel_internal_test.go
index 6cd18085ab302..3689bd37ac6f6 100644
--- a/vpn/tunnel_internal_test.go
+++ b/vpn/tunnel_internal_test.go
@@ -16,10 +16,11 @@ import (
 	"google.golang.org/protobuf/types/known/timestamppb"
 	"tailscale.com/util/dnsname"
 
+	"github.com/coder/quartz"
+
 	"github.com/coder/coder/v2/tailnet"
 	"github.com/coder/coder/v2/tailnet/proto"
 	"github.com/coder/coder/v2/testutil"
-	"github.com/coder/quartz"
 )
 
 func newFakeClient(ctx context.Context, t *testing.T) *fakeClient {
@@ -103,6 +104,9 @@ func TestTunnel_StartStop(t *testing.T) {
 					Headers: []*StartRequest_Header{
 						{Name: "X-Test-Header", Value: "test"},
 					},
+					DeviceOs:            "macOS",
+					DeviceId:            "device001",
+					CoderDesktopVersion: "0.24.8",
 				},
 			},
 		})
diff --git a/vpn/version.go b/vpn/version.go
index 1962dc36d4501..91aac9175f748 100644
--- a/vpn/version.go
+++ b/vpn/version.go
@@ -12,7 +12,11 @@ import (
 // implementation of the VPN RPC protocol.
 var CurrentSupportedVersions = RPCVersionList{
 	Versions: []RPCVersion{
-		{Major: 1, Minor: 0},
+		// 1.1 adds telemetry fields to StartRequest:
+		// - device_id: Coder Desktop device ID
+		// - device_os: Coder Desktop OS information
+		// - coder_desktop_version: Coder Desktop version
+		{Major: 1, Minor: 1},
 	},
 }
 
diff --git a/vpn/vpn.pb.go b/vpn/vpn.pb.go
index 863f11bba0a4b..db9b8ddd4ff75 100644
--- a/vpn/vpn.pb.go
+++ b/vpn/vpn.pb.go
@@ -957,6 +957,12 @@ type StartRequest struct {
 	CoderUrl             string                 `protobuf:"bytes,2,opt,name=coder_url,json=coderUrl,proto3" json:"coder_url,omitempty"`
 	ApiToken             string                 `protobuf:"bytes,3,opt,name=api_token,json=apiToken,proto3" json:"api_token,omitempty"`
 	Headers              []*StartRequest_Header `protobuf:"bytes,4,rep,name=headers,proto3" json:"headers,omitempty"`
+	// Device ID from Coder Desktop
+	DeviceId string `protobuf:"bytes,5,opt,name=device_id,json=deviceId,proto3" json:"device_id,omitempty"`
+	// Device OS from Coder Desktop
+	DeviceOs string `protobuf:"bytes,6,opt,name=device_os,json=deviceOs,proto3" json:"device_os,omitempty"`
+	// Coder Desktop version
+	CoderDesktopVersion string `protobuf:"bytes,7,opt,name=coder_desktop_version,json=coderDesktopVersion,proto3" json:"coder_desktop_version,omitempty"`
 }
 
 func (x *StartRequest) Reset() {
@@ -1019,6 +1025,27 @@ func (x *StartRequest) GetHeaders() []*StartRequest_Header {
 	return nil
 }
 
+func (x *StartRequest) GetDeviceId() string {
+	if x != nil {
+		return x.DeviceId
+	}
+	return ""
+}
+
+func (x *StartRequest) GetDeviceOs() string {
+	if x != nil {
+		return x.DeviceOs
+	}
+	return ""
+}
+
+func (x *StartRequest) GetCoderDesktopVersion() string {
+	if x != nil {
+		return x.CoderDesktopVersion
+	}
+	return ""
+}
+
 type StartResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -1839,7 +1866,7 @@ var file_vpn_vpn_proto_rawDesc = []byte{
 	0x73, 0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x18, 0x01, 0x20, 0x01, 0x28, 0x08, 0x52, 0x07, 0x73,
 	0x75, 0x63, 0x63, 0x65, 0x73, 0x73, 0x12, 0x23, 0x0a, 0x0d, 0x65, 0x72, 0x72, 0x6f, 0x72, 0x5f,
 	0x6d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x18, 0x02, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0c, 0x65,
-	0x72, 0x72, 0x6f, 0x72, 0x4d, 0x65, 0x73, 0x73, 0x61, 0x67, 0x65, 0x22, 0xe6, 0x01, 0x0a, 0x0c,
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@@ -1851,25 +1878,32 @@ var file_vpn_vpn_proto_rawDesc = []byte{
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 }
 
 var (
diff --git a/vpn/vpn.proto b/vpn/vpn.proto
index 10dfeb3916aa6..71a5994f88d54 100644
--- a/vpn/vpn.proto
+++ b/vpn/vpn.proto
@@ -185,6 +185,12 @@ message StartRequest {
 		string value = 2;
 	}
 	repeated Header headers = 4;
+	// Device ID from Coder Desktop
+	string device_id = 5;
+	// Device OS from Coder Desktop
+	string device_os = 6;
+	// Coder Desktop version
+	string coder_desktop_version = 7;
 }
 
 message StartResponse {