diff --git a/agent/agent.go b/agent/agent.go
index e2698e3304..f28af82aa8 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -120,14 +120,14 @@ type Options struct {
 }
 
 type Client interface {
-	ConnectRPC28(ctx context.Context) (
-		proto.DRPCAgentClient28, tailnetproto.DRPCTailnetClient28, error,
+	ConnectRPC29(ctx context.Context) (
+		proto.DRPCAgentClient29, tailnetproto.DRPCTailnetClient28, error,
 	)
-	// ConnectRPC28WithRole is like ConnectRPC28 but sends an explicit
+	// ConnectRPC29WithRole is like ConnectRPC29 but sends an explicit
 	// role query parameter to the server. The workspace agent should
 	// use role "agent" to enable connection monitoring.
-	ConnectRPC28WithRole(ctx context.Context, role string) (
-		proto.DRPCAgentClient28, tailnetproto.DRPCTailnetClient28, error,
+	ConnectRPC29WithRole(ctx context.Context, role string) (
+		proto.DRPCAgentClient29, tailnetproto.DRPCTailnetClient28, error,
 	)
 	tailnet.DERPMapRewriter
 	agentsdk.RefreshableSessionTokenProvider
@@ -1066,7 +1066,7 @@ func (a *agent) run() (retErr error) {
 	// ConnectRPC returns the dRPC connection we use for the Agent and Tailnet v2+ APIs.
 	// We pass role "agent" to enable connection monitoring on the server, which tracks
 	// the agent's connectivity state (first_connected_at, last_connected_at, disconnected_at).
-	aAPI, tAPI, err := a.client.ConnectRPC28WithRole(a.hardCtx, "agent")
+	aAPI, tAPI, err := a.client.ConnectRPC29WithRole(a.hardCtx, "agent")
 	if err != nil {
 		return err
 	}
diff --git a/agent/agentcontainers/subagent_test.go b/agent/agentcontainers/subagent_test.go
index 855ec47769..9b0d4a5019 100644
--- a/agent/agentcontainers/subagent_test.go
+++ b/agent/agentcontainers/subagent_test.go
@@ -81,7 +81,7 @@ func TestSubAgentClient_CreateWithDisplayApps(t *testing.T) {
 
 				agentAPI := agenttest.NewClient(t, logger, uuid.New(), agentsdk.Manifest{}, statsCh, tailnet.NewCoordinator(logger))
 
-				agentClient, _, err := agentAPI.ConnectRPC28(ctx)
+				agentClient, _, err := agentAPI.ConnectRPC29(ctx)
 				require.NoError(t, err)
 
 				subAgentClient := agentcontainers.NewSubAgentClientFromAPI(logger, agentClient)
@@ -245,7 +245,7 @@ func TestSubAgentClient_CreateWithDisplayApps(t *testing.T) {
 
 				agentAPI := agenttest.NewClient(t, logger, uuid.New(), agentsdk.Manifest{}, statsCh, tailnet.NewCoordinator(logger))
 
-				agentClient, _, err := agentAPI.ConnectRPC28(ctx)
+				agentClient, _, err := agentAPI.ConnectRPC29(ctx)
 				require.NoError(t, err)
 
 				subAgentClient := agentcontainers.NewSubAgentClientFromAPI(logger, agentClient)
diff --git a/agent/agenttest/client.go b/agent/agenttest/client.go
index b367252520..474469d7ff 100644
--- a/agent/agenttest/client.go
+++ b/agent/agenttest/client.go
@@ -140,14 +140,14 @@ func (c *Client) Close() {
 	c.derpMapOnce.Do(func() { close(c.derpMapUpdates) })
 }
 
-func (c *Client) ConnectRPC28WithRole(ctx context.Context, _ string) (
-	agentproto.DRPCAgentClient28, proto.DRPCTailnetClient28, error,
+func (c *Client) ConnectRPC29WithRole(ctx context.Context, _ string) (
+	agentproto.DRPCAgentClient29, proto.DRPCTailnetClient28, error,
 ) {
-	return c.ConnectRPC28(ctx)
+	return c.ConnectRPC29(ctx)
 }
 
-func (c *Client) ConnectRPC28(ctx context.Context) (
-	agentproto.DRPCAgentClient28, proto.DRPCTailnetClient28, error,
+func (c *Client) ConnectRPC29(ctx context.Context) (
+	agentproto.DRPCAgentClient29, proto.DRPCTailnetClient28, error,
 ) {
 	conn, lis := drpcsdk.MemTransportPipe()
 	c.LastWorkspaceAgent = func() {
diff --git a/agent/proto/agent.pb.go b/agent/proto/agent.pb.go
index 9da403f5df..36d264cc8e 100644
--- a/agent/proto/agent.pb.go
+++ b/agent/proto/agent.pb.go
@@ -3519,6 +3519,9 @@ type BoundaryLog struct {
 	//
 	//	*BoundaryLog_HttpRequest_
 	Resource isBoundaryLog_Resource `protobuf_oneof:"resource"`
+	// Monotonically increasing integer assigned by boundary, starting at 0
+	// per session. Primary ordering key when boundary is in use.
+	SequenceNumber int32 `protobuf:"varint,4,opt,name=sequence_number,json=sequenceNumber,proto3" json:"sequence_number,omitempty"`
 }
 
 func (x *BoundaryLog) Reset() {
@@ -3581,6 +3584,13 @@ func (x *BoundaryLog) GetHttpRequest() *BoundaryLog_HttpRequest {
 	return nil
 }
 
+func (x *BoundaryLog) GetSequenceNumber() int32 {
+	if x != nil {
+		return x.SequenceNumber
+	}
+	return 0
+}
+
 type isBoundaryLog_Resource interface {
 	isBoundaryLog_Resource()
 }
@@ -3598,6 +3608,13 @@ type ReportBoundaryLogsRequest struct {
 	unknownFields protoimpl.UnknownFields
 
 	Logs []*BoundaryLog `protobuf:"bytes,1,rep,name=logs,proto3" json:"logs,omitempty"`
+	// session_id identifies the boundary invocation that produced these
+	// logs. It is a UUID generated by boundary at startup and is the same
+	// for all batches produced by a single boundary run.
+	SessionId string `protobuf:"bytes,2,opt,name=session_id,json=sessionId,proto3" json:"session_id,omitempty"`
+	// confined_process is the name of the process that boundary is
+	// confining (e.g. "claude-code", "codex", "copilot").
+	ConfinedProcessName string `protobuf:"bytes,3,opt,name=confined_process_name,json=confinedProcessName,proto3" json:"confined_process_name,omitempty"`
 }
 
 func (x *ReportBoundaryLogsRequest) Reset() {
@@ -3639,6 +3656,20 @@ func (x *ReportBoundaryLogsRequest) GetLogs() []*BoundaryLog {
 	return nil
 }
 
+func (x *ReportBoundaryLogsRequest) GetSessionId() string {
+	if x != nil {
+		return x.SessionId
+	}
+	return ""
+}
+
+func (x *ReportBoundaryLogsRequest) GetConfinedProcessName() string {
+	if x != nil {
+		return x.ConfinedProcessName
+	}
+	return ""
+}
+
 type ReportBoundaryLogsResponse struct {
 	state         protoimpl.MessageState
 	sizeCache     protoimpl.SizeCache
@@ -5505,7 +5536,7 @@ var file_agent_proto_agent_proto_rawDesc = []byte{
 	0x65, 0x6e, 0x74, 0x73, 0x52, 0x65, 0x73, 0x70, 0x6f, 0x6e, 0x73, 0x65, 0x12, 0x30, 0x0a, 0x06,
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@@ -5516,164 +5547,172 @@ var file_agent_proto_agent_proto_rawDesc = []byte{
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+	0x6f, 0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
diff --git a/agent/proto/agent.proto b/agent/proto/agent.proto
index 27fa407c90..7e38f2f17e 100644
--- a/agent/proto/agent.proto
+++ b/agent/proto/agent.proto
@@ -500,11 +500,22 @@ message BoundaryLog {
 	oneof resource {
 		HttpRequest http_request = 3;
 	}
+
+	// Monotonically increasing integer assigned by boundary, starting at 0
+	// per session. Primary ordering key when boundary is in use.
+	int32 sequence_number = 4;
 }
 
 // ReportBoundaryLogsRequest is a request to re-emit the given BoundaryLogs.
 message ReportBoundaryLogsRequest {
 	repeated BoundaryLog logs = 1;
+	// session_id identifies the boundary invocation that produced these
+	// logs. It is a UUID generated by boundary at startup and is the same
+	// for all batches produced by a single boundary run.
+	string session_id = 2;
+	// confined_process is the name of the process that boundary is
+	// confining (e.g. "claude-code", "codex", "copilot").
+	string confined_process_name = 3;
 }
 
 message ReportBoundaryLogsResponse {}
diff --git a/agent/proto/agent_drpc_old.go b/agent/proto/agent_drpc_old.go
index 2d1a2810f1..9e21130027 100644
--- a/agent/proto/agent_drpc_old.go
+++ b/agent/proto/agent_drpc_old.go
@@ -83,3 +83,10 @@ type DRPCAgentClient28 interface {
 	DRPCAgentClient27
 	UpdateAppStatus(ctx context.Context, in *UpdateAppStatusRequest) (*UpdateAppStatusResponse, error)
 }
+
+// DRPCAgentClient29 is the Agent API at v2.9. It adds
+// session_id and confined_process fields to ReportBoundaryLogsRequest,
+// and sequence_number to BoundaryLog. No new RPCs.
+type DRPCAgentClient29 interface {
+	DRPCAgentClient28
+}
diff --git a/coderd/workspaceagents_test.go b/coderd/workspaceagents_test.go
index 8fffb1f5b1..74a41769b0 100644
--- a/coderd/workspaceagents_test.go
+++ b/coderd/workspaceagents_test.go
@@ -3139,7 +3139,7 @@ func requireGetManifest(ctx context.Context, t testing.TB, aAPI agentproto.DRPCA
 }
 
 func postStartup(ctx context.Context, t testing.TB, client agent.Client, startup *agentproto.Startup) error {
-	aAPI, _, err := client.ConnectRPC28(ctx)
+	aAPI, _, err := client.ConnectRPC29(ctx)
 	require.NoError(t, err)
 	defer func() {
 		cErr := aAPI.DRPCConn().Close()
diff --git a/codersdk/agentsdk/agentsdk.go b/codersdk/agentsdk/agentsdk.go
index b660db0f87..170cd3a98d 100644
--- a/codersdk/agentsdk/agentsdk.go
+++ b/codersdk/agentsdk/agentsdk.go
@@ -311,6 +311,31 @@ func (c *Client) ConnectRPC28WithRole(ctx context.Context, role string) (
 	return proto.NewDRPCAgentClient(conn), tailnetproto.NewDRPCTailnetClient(conn), nil
 }
 
+// ConnectRPC29 returns a dRPC client to the Agent API v2.9. It is useful when you want to be
+// maximally compatible with Coderd Release Versions from 2.32+
+func (c *Client) ConnectRPC29(ctx context.Context) (
+	proto.DRPCAgentClient29, tailnetproto.DRPCTailnetClient28, error,
+) {
+	conn, err := c.connectRPCVersion(ctx, apiversion.New(2, 9), "")
+	if err != nil {
+		return nil, nil, err
+	}
+	return proto.NewDRPCAgentClient(conn), tailnetproto.NewDRPCTailnetClient(conn), nil
+}
+
+// ConnectRPC29WithRole is like ConnectRPC29 but sends an explicit role
+// query parameter to the server. Use "agent" for workspace agents to
+// enable connection monitoring.
+func (c *Client) ConnectRPC29WithRole(ctx context.Context, role string) (
+	proto.DRPCAgentClient29, tailnetproto.DRPCTailnetClient28, error,
+) {
+	conn, err := c.connectRPCVersion(ctx, apiversion.New(2, 9), role)
+	if err != nil {
+		return nil, nil, err
+	}
+	return proto.NewDRPCAgentClient(conn), tailnetproto.NewDRPCTailnetClient(conn), nil
+}
+
 // ConnectRPC connects to the workspace agent API and tailnet API.
 // It does not send a role query parameter, so the server will apply
 // its default behavior (currently: enable connection monitoring for
diff --git a/scaletest/taskstatus/client.go b/scaletest/taskstatus/client.go
index 0ddc7b8627..59ef9e617e 100644
--- a/scaletest/taskstatus/client.go
+++ b/scaletest/taskstatus/client.go
@@ -150,7 +150,7 @@ func (u *sdkAppStatusUpdater) initialize(ctx context.Context, logger slog.Logger
 		codersdk.WithLogger(logger),
 		codersdk.WithLogBodies(),
 	)
-	drpcClient, _, err := agentClient.ConnectRPC28WithRole(ctx, "")
+	drpcClient, _, err := agentClient.ConnectRPC29WithRole(ctx, "")
 	if err != nil {
 		return xerrors.Errorf("connect to agent dRPC endpoint: %w", err)
 	}
diff --git a/tailnet/proto/version.go b/tailnet/proto/version.go
index 4fda6940a5..71c84ae7cc 100644
--- a/tailnet/proto/version.go
+++ b/tailnet/proto/version.go
@@ -64,9 +64,14 @@ import (
 // API v2.8:
 //   - Added support for pre-created sub agents on the Agent API.
 //   - Added support for UpdateAppStatus on the Agent API.
+//
+// API v2.9:
+//   - Added session_id and confined_process fields to
+//     ReportBoundaryLogsRequest on the Agent API.
+//   - Added sequence_number field to BoundaryLog on the Agent API.
 const (
 	CurrentMajor = 2
-	CurrentMinor = 8
+	CurrentMinor = 9
 )
 
 var CurrentVersion = apiversion.New(CurrentMajor, CurrentMinor)