diff --git a/audit/multi_auditor.go b/audit/multi_auditor.go
index a9be017..91607dc 100644
--- a/audit/multi_auditor.go
+++ b/audit/multi_auditor.go
@@ -5,6 +5,8 @@ import (
 	"fmt"
 	"log/slog"
 	"os"
+
+	"github.com/google/uuid"
 )
 
 // MultiAuditor wraps multiple auditors and sends audit events to all of them.
@@ -28,7 +30,7 @@ func (m *MultiAuditor) AuditRequest(req Request) {
 // provided configuration. It always includes a LogAuditor for stderr logging,
 // and conditionally adds a SocketAuditor if audit logs are enabled and the
 // workspace agent's log proxy socket exists.
-func SetupAuditor(ctx context.Context, logger *slog.Logger, disableAuditLogs bool, logProxySocketPath string) (Auditor, error) {
+func SetupAuditor(ctx context.Context, logger *slog.Logger, disableAuditLogs bool, logProxySocketPath string, sessionID uuid.UUID) (Auditor, error) {
 	stderrAuditor := NewLogAuditor(logger)
 	auditors := []Auditor{stderrAuditor}
 
@@ -48,7 +50,8 @@ func SetupAuditor(ctx context.Context, logger *slog.Logger, disableAuditLogs boo
 		}
 		agentWillProxy := !os.IsNotExist(err)
 		if agentWillProxy {
-			socketAuditor := NewSocketAuditor(logger, logProxySocketPath)
+			seq := &SequenceCounter{}
+			socketAuditor := NewSocketAuditor(logger, logProxySocketPath, sessionID, seq)
 			go socketAuditor.Loop(ctx)
 			auditors = append(auditors, socketAuditor)
 		} else {
diff --git a/audit/multi_auditor_test.go b/audit/multi_auditor_test.go
index e7f8af9..2293ff8 100644
--- a/audit/multi_auditor_test.go
+++ b/audit/multi_auditor_test.go
@@ -7,6 +7,8 @@ import (
 	"os"
 	"path/filepath"
 	"testing"
+
+	"github.com/google/uuid"
 )
 
 type mockAuditor struct {
@@ -25,7 +27,7 @@ func TestSetupAuditor_DisabledAuditLogs(t *testing.T) {
 	logger := slog.New(slog.NewTextHandler(io.Discard, nil))
 	ctx := context.Background()
 
-	auditor, err := SetupAuditor(ctx, logger, true, "")
+	auditor, err := SetupAuditor(ctx, logger, true, "", uuid.New())
 	if err != nil {
 		t.Fatalf("unexpected error: %v", err)
 	}
@@ -50,7 +52,7 @@ func TestSetupAuditor_EmptySocketPath(t *testing.T) {
 	logger := slog.New(slog.NewTextHandler(io.Discard, nil))
 	ctx := context.Background()
 
-	_, err := SetupAuditor(ctx, logger, false, "")
+	_, err := SetupAuditor(ctx, logger, false, "", uuid.New())
 	if err == nil {
 		t.Fatal("expected error for empty socket path, got nil")
 	}
@@ -62,7 +64,7 @@ func TestSetupAuditor_SocketDoesNotExist(t *testing.T) {
 	logger := slog.New(slog.NewTextHandler(io.Discard, nil))
 	ctx := context.Background()
 
-	auditor, err := SetupAuditor(ctx, logger, false, "/nonexistent/socket/path")
+	auditor, err := SetupAuditor(ctx, logger, false, "/nonexistent/socket/path", uuid.New())
 	if err != nil {
 		t.Fatalf("unexpected error: %v", err)
 	}
@@ -100,7 +102,7 @@ func TestSetupAuditor_SocketExists(t *testing.T) {
 		t.Fatalf("failed to close temp file: %v", err)
 	}
 
-	auditor, err := SetupAuditor(ctx, logger, false, socketPath)
+	auditor, err := SetupAuditor(ctx, logger, false, socketPath, uuid.New())
 	if err != nil {
 		t.Fatalf("unexpected error: %v", err)
 	}
diff --git a/audit/sequence.go b/audit/sequence.go
new file mode 100644
index 0000000..7882dd4
--- /dev/null
+++ b/audit/sequence.go
@@ -0,0 +1,20 @@
+package audit
+
+import "sync/atomic"
+
+// SequenceCounter is a monotonically increasing counter that assigns a
+// unique sequence number to every audit event within a single boundary
+// session. The counter starts at 0 and is safe for concurrent use by
+// both the socket auditor and the proxy.
+type SequenceCounter struct {
+	next atomic.Int32
+}
+
+// Next returns the next sequence number. The first call returns 0,
+// subsequent calls return 1, 2, 3, etc. It is safe for concurrent
+// use.
+func (c *SequenceCounter) Next() int32 {
+	// Add returns the new value after incrementing, so subtract 1
+	// to produce a zero-based sequence.
+	return c.next.Add(1) - 1
+}
diff --git a/audit/sequence_test.go b/audit/sequence_test.go
new file mode 100644
index 0000000..ffe51d3
--- /dev/null
+++ b/audit/sequence_test.go
@@ -0,0 +1,25 @@
+package audit
+
+import (
+	"testing"
+)
+
+func TestSequenceCounter_StartsAtZero(t *testing.T) {
+	t.Parallel()
+
+	var c SequenceCounter
+	if got := c.Next(); got != 0 {
+		t.Fatalf("first call: got %d, want 0", got)
+	}
+}
+
+func TestSequenceCounter_Increments(t *testing.T) {
+	t.Parallel()
+
+	var c SequenceCounter
+	for i := range int32(100) {
+		if got := c.Next(); got != i {
+			t.Fatalf("call %d: got %d, want %d", i, got, i)
+		}
+	}
+}
diff --git a/audit/socket_auditor.go b/audit/socket_auditor.go
index 4c8c5d8..afb50a3 100644
--- a/audit/socket_auditor.go
+++ b/audit/socket_auditor.go
@@ -8,6 +8,7 @@ import (
 	"sync/atomic"
 	"time"
 
+	"github.com/google/uuid"
 	"google.golang.org/protobuf/types/known/timestamppb"
 
 	"github.com/coder/coder/v2/agent/boundarylogproxy/codec"
@@ -34,6 +35,8 @@ type SocketAuditor struct {
 	batchSize          int
 	batchTimerDuration time.Duration
 	socketPath         string
+	sessionID          uuid.UUID
+	seq                *SequenceCounter
 
 	droppedChannelFull atomic.Int64
 	droppedBatchFull   atomic.Int64
@@ -45,7 +48,7 @@ type SocketAuditor struct {
 // NewSocketAuditor creates a new SocketAuditor that sends logs to the agent's
 // boundary log proxy socket after SocketAuditor.Loop is called. The socket path
 // is read from EnvAuditSocketPath, falling back to defaultAuditSocketPath.
-func NewSocketAuditor(logger *slog.Logger, socketPath string) *SocketAuditor {
+func NewSocketAuditor(logger *slog.Logger, socketPath string, sessionID uuid.UUID, seq *SequenceCounter) *SocketAuditor {
 	// This channel buffer size intends to allow enough buffering for bursty
 	// AI agent network requests while a batch is being sent to the workspace
 	// agent.
@@ -60,6 +63,8 @@ func NewSocketAuditor(logger *slog.Logger, socketPath string) *SocketAuditor {
 		batchSize:          defaultBatchSize,
 		batchTimerDuration: defaultBatchTimerDuration,
 		socketPath:         socketPath,
+		sessionID:          sessionID,
+		seq:                seq,
 	}
 }
 
@@ -77,9 +82,10 @@ func (s *SocketAuditor) AuditRequest(req Request) {
 	}
 
 	log := &agentproto.BoundaryLog{
-		Allowed:  req.Allowed,
-		Time:     timestamppb.Now(),
-		Resource: &agentproto.BoundaryLog_HttpRequest_{HttpRequest: httpReq},
+		Allowed:        req.Allowed,
+		Time:           timestamppb.Now(),
+		SequenceNumber: s.seq.Next(),
+		Resource:       &agentproto.BoundaryLog_HttpRequest_{HttpRequest: httpReq},
 	}
 
 	select {
@@ -100,14 +106,17 @@ type flushErr struct {
 func (e *flushErr) Error() string { return e.err.Error() }
 
 // flush sends the current batch of logs to the given connection.
-func flush(conn net.Conn, logs []*agentproto.BoundaryLog) *flushErr {
+func flush(conn net.Conn, sessionID uuid.UUID, logs []*agentproto.BoundaryLog) *flushErr {
 	if len(logs) == 0 {
 		return nil
 	}
 
 	msg := &codec.BoundaryMessage{
 		Msg: &codec.BoundaryMessage_Logs{
-			Logs: &agentproto.ReportBoundaryLogsRequest{Logs: logs},
+			Logs: &agentproto.ReportBoundaryLogsRequest{
+				Logs:      logs,
+				SessionId: sessionID.String(),
+			},
 		},
 	}
 	if err := codec.WriteMessage(conn, codec.TagV2, msg); err != nil {
@@ -188,7 +197,7 @@ func (s *SocketAuditor) Loop(ctx context.Context) {
 			return
 		}
 
-		if err := flush(conn, batch); err != nil {
+		if err := flush(conn, s.sessionID, batch); err != nil {
 			if err.permanent {
 				// Data error: discard batch to avoid infinite retries.
 				s.logger.Warn("dropping batch due to data error on flush attempt",
diff --git a/audit/socket_auditor_test.go b/audit/socket_auditor_test.go
index 67ebbae..6443781 100644
--- a/audit/socket_auditor_test.go
+++ b/audit/socket_auditor_test.go
@@ -11,6 +11,8 @@ import (
 	"testing"
 	"time"
 
+	"github.com/google/uuid"
+
 	"github.com/coder/coder/v2/agent/boundarylogproxy/codec"
 	agentproto "github.com/coder/coder/v2/agent/proto"
 )
@@ -33,6 +35,15 @@ func TestSocketAuditor_AuditRequest_QueuesLog(t *testing.T) {
 		if log.Allowed != true {
 			t.Errorf("expected Allowed=true, got %v", log.Allowed)
 		}
+		if log.Time == nil {
+			t.Fatal("expected Time to be set")
+		}
+		if log.Time.AsTime().IsZero() {
+			t.Fatal("expected Time to not be the zero time")
+		}
+		if log.SequenceNumber != 0 {
+			t.Errorf("expected first SequenceNumber=0, got %d", log.SequenceNumber)
+		}
 		httpReq := log.GetHttpRequest()
 		if httpReq == nil {
 			t.Fatal("expected HttpRequest, got nil")
@@ -230,6 +241,8 @@ func TestSocketAuditor_Loop_RetriesOnConnectionFailure(t *testing.T) {
 		logCh:              make(chan *agentproto.BoundaryLog, 2*defaultBatchSize),
 		batchSize:          defaultBatchSize,
 		batchTimerDuration: time.Hour, // Ensure timer doesn't interfere with the test
+		sessionID:          uuid.MustParse("00000000-0000-4000-8000-000000000001"),
+		seq:                &SequenceCounter{},
 	}
 
 	// Set up hook to detect flush attempts
@@ -349,6 +362,8 @@ func TestSocketAuditor_Loop_ReportsBatchFullDrops(t *testing.T) {
 		logCh:              make(chan *agentproto.BoundaryLog, 2*defaultBatchSize),
 		batchSize:          defaultBatchSize,
 		batchTimerDuration: time.Hour,
+		sessionID:          uuid.MustParse("00000000-0000-4000-8000-000000000001"),
+		seq:                &SequenceCounter{},
 	}
 
 	flushed := make(chan struct{}, 4)
@@ -451,17 +466,75 @@ func TestSocketAuditor_Loop_ShutdownFlushIncludesDrops(t *testing.T) {
 func TestFlush_EmptyBatch(t *testing.T) {
 	t.Parallel()
 
-	err := flush(nil, nil)
+	err := flush(nil, uuid.Nil, nil)
 	if err != nil {
 		t.Errorf("expected nil error for empty batch, got %v", err)
 	}
 
-	err = flush(nil, []*agentproto.BoundaryLog{})
+	err = flush(nil, uuid.Nil, []*agentproto.BoundaryLog{})
 	if err != nil {
 		t.Errorf("expected nil error for empty slice, got %v", err)
 	}
 }
 
+func TestSocketAuditor_AuditRequest_SequenceNumberIncrements(t *testing.T) {
+	t.Parallel()
+
+	auditor := setupSocketAuditor(t)
+
+	for i := range 5 {
+		auditor.AuditRequest(Request{Method: "GET", URL: "https://example.com", Allowed: true})
+
+		select {
+		case log := <-auditor.logCh:
+			if log.SequenceNumber != int32(i) {
+				t.Errorf("request %d: expected SequenceNumber=%d, got %d", i, i, log.SequenceNumber)
+			}
+		default:
+			t.Fatalf("request %d: expected log in channel, got none", i)
+		}
+	}
+}
+
+func TestSocketAuditor_Loop_FlushIncludesSessionID(t *testing.T) {
+	t.Parallel()
+
+	auditor, serverConn := setupTestAuditor(t)
+	auditor.batchTimerDuration = time.Hour
+
+	cr := newConnReader()
+	go readFromConn(t, serverConn, cr)
+
+	go auditor.Loop(t.Context())
+
+	// Fill a batch to trigger a flush.
+	for i := 0; i < auditor.batchSize; i++ {
+		auditor.AuditRequest(Request{Method: "GET", URL: "https://example.com", Allowed: true})
+	}
+
+	select {
+	case req := <-cr.logs:
+		expectedSessionID := uuid.MustParse("00000000-0000-4000-8000-000000000001").String()
+		if req.SessionId != expectedSessionID {
+			t.Errorf("expected SessionId=%s, got %q", expectedSessionID, req.SessionId)
+		}
+		if len(req.Logs) != auditor.batchSize {
+			t.Errorf("expected %d logs, got %d", auditor.batchSize, len(req.Logs))
+		}
+		// Verify sequence numbers are monotonically increasing.
+		for i, log := range req.Logs {
+			if log.SequenceNumber != int32(i) {
+				t.Errorf("log %d: expected SequenceNumber=%d, got %d", i, i, log.SequenceNumber)
+			}
+			if log.Time == nil {
+				t.Errorf("log %d: expected Time to be set", i)
+			}
+		}
+	case <-time.After(5 * time.Second):
+		t.Fatal("timeout waiting for flush")
+	}
+}
+
 // setupSocketAuditor creates a SocketAuditor for tests that only exercise
 // the queueing behavior (no connection needed).
 func setupSocketAuditor(t *testing.T) *SocketAuditor {
@@ -475,6 +548,8 @@ func setupSocketAuditor(t *testing.T) *SocketAuditor {
 		logCh:              make(chan *agentproto.BoundaryLog, 2*defaultBatchSize),
 		batchSize:          defaultBatchSize,
 		batchTimerDuration: defaultBatchTimerDuration,
+		sessionID:          uuid.MustParse("00000000-0000-4000-8000-000000000001"),
+		seq:                &SequenceCounter{},
 	}
 }
 
@@ -504,6 +579,8 @@ func setupTestAuditor(t *testing.T) (*SocketAuditor, net.Conn) {
 		logCh:              make(chan *agentproto.BoundaryLog, 2*defaultBatchSize),
 		batchSize:          defaultBatchSize,
 		batchTimerDuration: defaultBatchTimerDuration,
+		sessionID:          uuid.MustParse("00000000-0000-4000-8000-000000000001"),
+		seq:                &SequenceCounter{},
 	}
 
 	return auditor, serverConn
diff --git a/config/config.go b/config/config.go
index d688834..73cdb38 100644
--- a/config/config.go
+++ b/config/config.go
@@ -5,6 +5,7 @@ import (
 	"strings"
 
 	"github.com/coder/serpent"
+	"github.com/google/uuid"
 	"github.com/spf13/pflag"
 )
 
@@ -85,6 +86,11 @@ type AppConfig struct {
 	UserInfo           *UserInfo
 	DisableAuditLogs   bool
 	LogProxySocketPath string
+
+	// SessionID is a UUIDv4 generated at process startup. It groups
+	// all audit events produced by this boundary invocation into a
+	// single session. Set by Run, not by configuration.
+	SessionID uuid.UUID
 }
 
 func NewAppConfigFromCliConfig(cfg CliConfig, targetCMD []string) (AppConfig, error) {
diff --git a/go.mod b/go.mod
index 0188e84..a5e4732 100644
--- a/go.mod
+++ b/go.mod
@@ -1,21 +1,22 @@
 module github.com/coder/boundary
 
-go 1.25.7
+go 1.25.9
 
 require (
 	github.com/cenkalti/backoff/v5 v5.0.3
-	github.com/coder/coder/v2 v2.10.1-0.20260303212958-f758443f44ac
+	github.com/coder/coder/v2 v2.33.0-rc.3.0.20260501075247-b3e1178358f5
 	github.com/coder/serpent v0.14.0
+	github.com/google/uuid v1.6.0
 	github.com/landlock-lsm/go-landlock v0.0.0-20251103212306-430f8e5cd97c
 	github.com/miekg/dns v1.1.72
 	github.com/spf13/pflag v1.0.10
 	github.com/stretchr/testify v1.11.1
-	golang.org/x/sys v0.41.0
+	golang.org/x/sys v0.43.0
 	google.golang.org/protobuf v1.36.11
 )
 
 require (
-	cdr.dev/slog/v3 v3.0.0-rc1 // indirect
+	cdr.dev/slog/v3 v3.0.0 // indirect
 	github.com/aymanbagabas/go-osc52/v2 v2.0.1 // indirect
 	github.com/beorn7/perks v1.0.1 // indirect
 	github.com/cespare/xxhash/v2 v2.3.0 // indirect
@@ -38,16 +39,16 @@ require (
 	github.com/rivo/uniseg v0.4.7 // indirect
 	github.com/xhit/go-str2duration/v2 v2.1.0 // indirect
 	github.com/zeebo/errs v1.4.0 // indirect
-	go.opentelemetry.io/otel v1.40.0 // indirect
-	go.opentelemetry.io/otel/trace v1.40.0 // indirect
+	go.opentelemetry.io/otel v1.43.0 // indirect
+	go.opentelemetry.io/otel/trace v1.43.0 // indirect
 	go.yaml.in/yaml/v2 v2.4.3 // indirect
-	golang.org/x/crypto v0.48.0 // indirect
+	golang.org/x/crypto v0.50.0 // indirect
 	golang.org/x/exp v0.0.0-20260218203240-3dfff04db8fa // indirect
-	golang.org/x/mod v0.33.0 // indirect
-	golang.org/x/net v0.50.0 // indirect
-	golang.org/x/sync v0.19.0 // indirect
-	golang.org/x/term v0.40.0 // indirect
-	golang.org/x/tools v0.42.0 // indirect
+	golang.org/x/mod v0.35.0 // indirect
+	golang.org/x/net v0.53.0 // indirect
+	golang.org/x/sync v0.20.0 // indirect
+	golang.org/x/term v0.42.0 // indirect
+	golang.org/x/tools v0.44.0 // indirect
 	golang.org/x/xerrors v0.0.0-20240903120638-7835f813f4da // indirect
 	gopkg.in/yaml.v3 v3.0.1 // indirect
 	kernel.org/pub/linux/libs/security/libcap/psx v1.2.77 // indirect
diff --git a/go.sum b/go.sum
index d04ae6c..89d4da8 100644
--- a/go.sum
+++ b/go.sum
@@ -1,5 +1,5 @@
-cdr.dev/slog/v3 v3.0.0-rc1 h1:EN7Zim6GvTpAeHQjI0ERDEfqKbTyXRvgH4UhlzLpvWM=
-cdr.dev/slog/v3 v3.0.0-rc1/go.mod h1:iO/OALX1VxlI03mkodCGdVP7pXzd2bRMvu3ePvlJ9ak=
+cdr.dev/slog/v3 v3.0.0 h1:kXFUqAqK7ogRKcvo4BnduQVp+Jh0uV1AUKf3NW5FU74=
+cdr.dev/slog/v3 v3.0.0/go.mod h1:iO/OALX1VxlI03mkodCGdVP7pXzd2bRMvu3ePvlJ9ak=
 cloud.google.com/go v0.123.0 h1:2NAUJwPR47q+E35uaJeYoNhuNEM9kM8SjgRgdeOJUSE=
 cloud.google.com/go/compute v1.23.0 h1:tP41Zoavr8ptEqaW6j+LQOnyBBhO7OkOMAGrgLopTwY=
 cloud.google.com/go/compute/metadata v0.9.0 h1:pDUj4QMoPejqq20dK0Pg2N4yG9zIkYGdBtwLoEkH9Zs=
@@ -28,14 +28,12 @@ github.com/charmbracelet/x/cellbuf v0.0.15 h1:ur3pZy0o6z/R7EylET877CBxaiE1Sp1GMx
 github.com/charmbracelet/x/cellbuf v0.0.15/go.mod h1:J1YVbR7MUuEGIFPCaaZ96KDl5NoS0DAWkskup+mOY+Q=
 github.com/charmbracelet/x/term v0.2.2 h1:xVRT/S2ZcKdhhOuSP4t5cLi5o+JxklsoEObBSgfgZRk=
 github.com/charmbracelet/x/term v0.2.2/go.mod h1:kF8CY5RddLWrsgVwpw4kAa6TESp6EB5y3uxGLeCqzAI=
-github.com/clipperhouse/displaywidth v0.9.0 h1:Qb4KOhYwRiN3viMv1v/3cTBlz3AcAZX3+y9OLhMtAtA=
-github.com/clipperhouse/displaywidth v0.9.0/go.mod h1:aCAAqTlh4GIVkhQnJpbL0T/WfcrJXHcj8C0yjYcjOZA=
-github.com/clipperhouse/stringish v0.1.1 h1:+NSqMOr3GR6k1FdRhhnXrLfztGzuG+VuFDfatpWHKCs=
-github.com/clipperhouse/stringish v0.1.1/go.mod h1:v/WhFtE1q0ovMta2+m+UbpZ+2/HEXNWYXQgCt4hdOzA=
-github.com/clipperhouse/uax29/v2 v2.5.0 h1:x7T0T4eTHDONxFJsL94uKNKPHrclyFI0lm7+w94cO8U=
-github.com/clipperhouse/uax29/v2 v2.5.0/go.mod h1:Wn1g7MK6OoeDT0vL+Q0SQLDz/KpfsVRgg6W7ihQeh4g=
-github.com/coder/coder/v2 v2.10.1-0.20260303212958-f758443f44ac h1:BmOs70CvLwP7dUt245ffapnSfMME0/tmI2M9nMi6O/w=
-github.com/coder/coder/v2 v2.10.1-0.20260303212958-f758443f44ac/go.mod h1:ZyamF6ltx68UIQjbzUchKUTedpUIoyQlwCpOk5c+U4E=
+github.com/clipperhouse/displaywidth v0.10.0 h1:GhBG8WuerxjFQQYeuZAeVTuyxuX+UraiZGD4HJQ3Y8g=
+github.com/clipperhouse/displaywidth v0.10.0/go.mod h1:XqJajYsaiEwkxOj4bowCTMcT1SgvHo9flfF3jQasdbs=
+github.com/clipperhouse/uax29/v2 v2.6.0 h1:z0cDbUV+aPASdFb2/ndFnS9ts/WNXgTNNGFoKXuhpos=
+github.com/clipperhouse/uax29/v2 v2.6.0/go.mod h1:Wn1g7MK6OoeDT0vL+Q0SQLDz/KpfsVRgg6W7ihQeh4g=
+github.com/coder/coder/v2 v2.33.0-rc.3.0.20260501075247-b3e1178358f5 h1:7V2ZTceP3V8EqYA8kC+3xrRwaZ8SOtgw4b8cElm0rcA=
+github.com/coder/coder/v2 v2.33.0-rc.3.0.20260501075247-b3e1178358f5/go.mod h1:w3FcuW2hJS/QnmY7ilsvt0yVpUhlVYdnBozwTkmpkKE=
 github.com/coder/pretty v0.0.0-20230908205945-e89ba86370e0 h1:3A0ES21Ke+FxEM8CXx9n47SZOKOpgSE1bbJzlE4qPVs=
 github.com/coder/pretty v0.0.0-20230908205945-e89ba86370e0/go.mod h1:5UuS2Ts+nTToAMeOjNlnHFkPahrtDkmpydBen/3wgZc=
 github.com/coder/serpent v0.14.0 h1:g7vt2zBMp3nWyAvyhvQduaI53Ku65U3wITMi01+/8pU=
@@ -131,14 +129,14 @@ github.com/zeebo/errs v1.4.0 h1:XNdoD/RRMKP7HD0UhJnIzUy74ISdGGxURlYG8HSWSfM=
 github.com/zeebo/errs v1.4.0/go.mod h1:sgbWHsvVuTPHcqJJGQ1WhI5KbWlHYz+2+2C/LSEtCw4=
 go.opentelemetry.io/auto/sdk v1.2.1 h1:jXsnJ4Lmnqd11kwkBV2LgLoFMZKizbCi5fNZ/ipaZ64=
 go.opentelemetry.io/auto/sdk v1.2.1/go.mod h1:KRTj+aOaElaLi+wW1kO/DZRXwkF4C5xPbEe3ZiIhN7Y=
-go.opentelemetry.io/otel v1.40.0 h1:oA5YeOcpRTXq6NN7frwmwFR0Cn3RhTVZvXsP4duvCms=
-go.opentelemetry.io/otel v1.40.0/go.mod h1:IMb+uXZUKkMXdPddhwAHm6UfOwJyh4ct1ybIlV14J0g=
-go.opentelemetry.io/otel/metric v1.40.0 h1:rcZe317KPftE2rstWIBitCdVp89A2HqjkxR3c11+p9g=
-go.opentelemetry.io/otel/metric v1.40.0/go.mod h1:ib/crwQH7N3r5kfiBZQbwrTge743UDc7DTFVZrrXnqc=
-go.opentelemetry.io/otel/sdk v1.40.0 h1:KHW/jUzgo6wsPh9At46+h4upjtccTmuZCFAc9OJ71f8=
-go.opentelemetry.io/otel/sdk v1.40.0/go.mod h1:Ph7EFdYvxq72Y8Li9q8KebuYUr2KoeyHx0DRMKrYBUE=
-go.opentelemetry.io/otel/trace v1.40.0 h1:WA4etStDttCSYuhwvEa8OP8I5EWu24lkOzp+ZYblVjw=
-go.opentelemetry.io/otel/trace v1.40.0/go.mod h1:zeAhriXecNGP/s2SEG3+Y8X9ujcJOTqQ5RgdEJcawiA=
+go.opentelemetry.io/otel v1.43.0 h1:mYIM03dnh5zfN7HautFE4ieIig9amkNANT+xcVxAj9I=
+go.opentelemetry.io/otel v1.43.0/go.mod h1:JuG+u74mvjvcm8vj8pI5XiHy1zDeoCS2LB1spIq7Ay0=
+go.opentelemetry.io/otel/metric v1.43.0 h1:d7638QeInOnuwOONPp4JAOGfbCEpYb+K6DVWvdxGzgM=
+go.opentelemetry.io/otel/metric v1.43.0/go.mod h1:RDnPtIxvqlgO8GRW18W6Z/4P462ldprJtfxHxyKd2PY=
+go.opentelemetry.io/otel/sdk v1.43.0 h1:pi5mE86i5rTeLXqoF/hhiBtUNcrAGHLKQdhg4h4V9Dg=
+go.opentelemetry.io/otel/sdk v1.43.0/go.mod h1:P+IkVU3iWukmiit/Yf9AWvpyRDlUeBaRg6Y+C58QHzg=
+go.opentelemetry.io/otel/trace v1.43.0 h1:BkNrHpup+4k4w+ZZ86CZoHHEkohws8AY+WTX09nk+3A=
+go.opentelemetry.io/otel/trace v1.43.0/go.mod h1:/QJhyVBUUswCphDVxq+8mld+AvhXZLhe+8WVFxiFff0=
 go.uber.org/goleak v1.3.1-0.20240429205332-517bace7cc29 h1:w0QrHuh0hhUZ++UTQaBM2DMdrWQghZ/UsUb+Wb1+8YE=
 go.uber.org/goleak v1.3.1-0.20240429205332-517bace7cc29/go.mod h1:CoHD4mav9JJNrW/WLlf7HGZPjdw8EucARQHekz1X6bE=
 go.yaml.in/yaml/v2 v2.4.3 h1:6gvOSjQoTB3vt1l+CU+tSyi/HOjfOjRLJ4YwYZGwRO0=
@@ -146,14 +144,14 @@ go.yaml.in/yaml/v2 v2.4.3/go.mod h1:zSxWcmIDjOzPXpjlTTbAsKokqkDNAVtZO0WOMiT90s8=
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20210921155107-089bfa567519/go.mod h1:GvvjBRRGRdwPK5ydBHafDWAxML/pGHZbMvKqRZ5+Abc=
 golang.org/x/crypto v0.12.0/go.mod h1:NF0Gs7EO5K4qLn+Ylc+fih8BSTeIjAP05siRnAh98yw=
-golang.org/x/crypto v0.48.0 h1:/VRzVqiRSggnhY7gNRxPauEQ5Drw9haKdM0jqfcCFts=
-golang.org/x/crypto v0.48.0/go.mod h1:r0kV5h3qnFPlQnBSrULhlsRfryS2pmewsg+XfMgkVos=
+golang.org/x/crypto v0.50.0 h1:zO47/JPrL6vsNkINmLoo/PH1gcxpls50DNogFvB5ZGI=
+golang.org/x/crypto v0.50.0/go.mod h1:3muZ7vA7PBCE6xgPX7nkzzjiUq87kRItoJQM1Yo8S+Q=
 golang.org/x/exp v0.0.0-20260218203240-3dfff04db8fa h1:Zt3DZoOFFYkKhDT3v7Lm9FDMEV06GpzjG2jrqW+QTE0=
 golang.org/x/exp v0.0.0-20260218203240-3dfff04db8fa/go.mod h1:K79w1Vqn7PoiZn+TkNpx3BUWUQksGO3JcVX6qIjytmA=
 golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4/go.mod h1:jJ57K6gSWd91VN4djpZkiMVwK6gcyfeH4XE8wZrZaV4=
 golang.org/x/mod v0.8.0/go.mod h1:iBbtSCu2XBx23ZKBPSOrRkjjQPZFPuis4dIYUhu/chs=
-golang.org/x/mod v0.33.0 h1:tHFzIWbBifEmbwtGz65eaWyGiGZatSrT9prnU8DbVL8=
-golang.org/x/mod v0.33.0/go.mod h1:swjeQEj+6r7fODbD2cqrnje9PnziFuw4bmLbBZFrQ5w=
+golang.org/x/mod v0.35.0 h1:Ww1D637e6Pg+Zb2KrWfHQUnH2dQRLBQyAtpr/haaJeM=
+golang.org/x/mod v0.35.0/go.mod h1:+GwiRhIInF8wPm+4AoT6L0FA1QWAad3OMdTRx4tFYlU=
 golang.org/x/net v0.0.0-20190620200207-3b0461eec859/go.mod h1:z5CRVTTTmAJ677TzLLGU+0bjPO0LkuOLi4/5GtJWs/s=
 golang.org/x/net v0.0.0-20210226172049-e18ecbb05110/go.mod h1:m0MpNAwzfU5UDzcl9v0D8zg8gWTRqZa9RBIspLL5mdg=
 golang.org/x/net v0.0.0-20220722155237-a158d28d115b/go.mod h1:XRhObCWvk6IyKnWLug+ECip1KBveYUHfp+8e9klMJ9c=
@@ -161,15 +159,15 @@ golang.org/x/net v0.1.0/go.mod h1:Cx3nUiGt4eDBEyega/BKRp+/AlGL8hYe7U9odMt2Cco=
 golang.org/x/net v0.6.0/go.mod h1:2Tu9+aMcznHK/AK1HMvgo6xiTLG5rD5rZLDS+rp2Bjs=
 golang.org/x/net v0.10.0/go.mod h1:0qNGK6F8kojg2nk9dLZ2mShWaEBan6FAoqfSigmmuDg=
 golang.org/x/net v0.14.0/go.mod h1:PpSgVXXLK0OxS0F31C1/tv6XNguvCrnXIDrFMspZIUI=
-golang.org/x/net v0.50.0 h1:ucWh9eiCGyDR3vtzso0WMQinm2Dnt8cFMuQa9K33J60=
-golang.org/x/net v0.50.0/go.mod h1:UgoSli3F/pBgdJBHCTc+tp3gmrU4XswgGRgtnwWTfyM=
-golang.org/x/oauth2 v0.35.0 h1:Mv2mzuHuZuY2+bkyWXIHMfhNdJAdwW3FuWeCPYN5GVQ=
-golang.org/x/oauth2 v0.35.0/go.mod h1:lzm5WQJQwKZ3nwavOZ3IS5Aulzxi68dUSgRHujetwEA=
+golang.org/x/net v0.53.0 h1:d+qAbo5L0orcWAr0a9JweQpjXF19LMXJE8Ey7hwOdUA=
+golang.org/x/net v0.53.0/go.mod h1:JvMuJH7rrdiCfbeHoo3fCQU24Lf5JJwT9W3sJFulfgs=
+golang.org/x/oauth2 v0.36.0 h1:peZ/1z27fi9hUOFCAZaHyrpWG5lwe0RJEEEeH0ThlIs=
+golang.org/x/oauth2 v0.36.0/go.mod h1:YDBUJMTkDnJS+A4BP4eZBjCqtokkg1hODuPjwiGPO7Q=
 golang.org/x/sync v0.0.0-20190423024810-112230192c58/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.0.0-20220722155255-886fb9371eb4/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.1.0/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
-golang.org/x/sync v0.19.0 h1:vV+1eWNmZ5geRlYjzm2adRgW2/mcpevXNg50YZtPCE4=
-golang.org/x/sync v0.19.0/go.mod h1:9KTHXmSnoGruLpwFjVSX0lNNA75CykiMECbovNTZqGI=
+golang.org/x/sync v0.20.0 h1:e0PTpb7pjO8GAtTs2dQ6jYa5BWYlMuX047Dco/pItO4=
+golang.org/x/sync v0.20.0/go.mod h1:9xrNwdLfx4jkKbNva9FpL6vEN7evnE43NNNJQ2LF3+0=
 golang.org/x/sys v0.0.0-20190215142949-d0b11bdaac8a/go.mod h1:STP8DvDyc/dI5b8T5hshtkjS+E42TnysNCUPdjciGhY=
 golang.org/x/sys v0.0.0-20201119102817-f84b799fce68/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210615035016-665e8c7367d1/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
@@ -181,16 +179,16 @@ golang.org/x/sys v0.5.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.6.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.8.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.11.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
-golang.org/x/sys v0.41.0 h1:Ivj+2Cp/ylzLiEU89QhWblYnOE9zerudt9Ftecq2C6k=
-golang.org/x/sys v0.41.0/go.mod h1:OgkHotnGiDImocRcuBABYBEXf8A9a87e/uXjp9XT3ks=
+golang.org/x/sys v0.43.0 h1:Rlag2XtaFTxp19wS8MXlJwTvoh8ArU6ezoyFsMyCTNI=
+golang.org/x/sys v0.43.0/go.mod h1:4GL1E5IUh+htKOUEOaiffhrAeqysfVGipDYzABqnCmw=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
 golang.org/x/term v0.0.0-20210927222741-03fcf44c2211/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
 golang.org/x/term v0.1.0/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
 golang.org/x/term v0.5.0/go.mod h1:jMB1sMXY+tzblOD4FWmEbocvup2/aLOaQEp7JmGp78k=
 golang.org/x/term v0.8.0/go.mod h1:xPskH00ivmX89bAKVGSKKtLOWNx2+17Eiy94tnKShWo=
 golang.org/x/term v0.11.0/go.mod h1:zC9APTIj3jG3FdV/Ons+XE1riIZXG4aZ4GTHiPZJPIU=
-golang.org/x/term v0.40.0 h1:36e4zGLqU4yhjlmxEaagx2KuYbJq3EwY8K943ZsHcvg=
-golang.org/x/term v0.40.0/go.mod h1:w2P8uVp06p2iyKKuvXIm7N/y0UCRt3UfJTfZ7oOpglM=
+golang.org/x/term v0.42.0 h1:UiKe+zDFmJobeJ5ggPwOshJIVt6/Ft0rcfrXZDLWAWY=
+golang.org/x/term v0.42.0/go.mod h1:Dq/D+snpsbazcBG5+F9Q1n2rXV8Ma+71xEjTRufARgY=
 golang.org/x/text v0.3.0/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
 golang.org/x/text v0.3.3/go.mod h1:5Zoc/QRtKVWzQhOtBMvqHzDpF6irO9z98xDceosuGiQ=
 golang.org/x/text v0.3.7/go.mod h1:u+2+/6zg+i71rQMx5EYifcz6MCKuco9NR6JIITiCfzQ=
@@ -198,25 +196,25 @@ golang.org/x/text v0.4.0/go.mod h1:mrYo+phRRbMaCq/xk9113O4dZlRixOauAjOtrjsXDZ8=
 golang.org/x/text v0.7.0/go.mod h1:mrYo+phRRbMaCq/xk9113O4dZlRixOauAjOtrjsXDZ8=
 golang.org/x/text v0.9.0/go.mod h1:e1OnstbJyHTd6l/uOt8jFFHp6TRDWZR/bV3emEE/zU8=
 golang.org/x/text v0.12.0/go.mod h1:TvPlkZtksWOMsz7fbANvkp4WM8x/WCo/om8BMLbz+aE=
-golang.org/x/text v0.34.0 h1:oL/Qq0Kdaqxa1KbNeMKwQq0reLCCaFtqu2eNuSeNHbk=
-golang.org/x/text v0.34.0/go.mod h1:homfLqTYRFyVYemLBFl5GgL/DWEiH5wcsQ5gSh1yziA=
+golang.org/x/text v0.36.0 h1:JfKh3XmcRPqZPKevfXVpI1wXPTqbkE5f7JA92a55Yxg=
+golang.org/x/text v0.36.0/go.mod h1:NIdBknypM8iqVmPiuco0Dh6P5Jcdk8lJL0CUebqK164=
 golang.org/x/tools v0.0.0-20180917221912-90fa682c2a6e/go.mod h1:n7NCudcB/nEzxVGmLbDWY5pfWTLqBcC2KZ6jyYvM4mQ=
 golang.org/x/tools v0.0.0-20191119224855-298f0cb1881e/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.1.12/go.mod h1:hNGJHUnrk76NpqgfD5Aqm5Crs+Hm0VOH/i9J2+nxYbc=
 golang.org/x/tools v0.6.0/go.mod h1:Xwgl3UAJ/d3gWutnCtw505GrjyAbvKui8lOU390QaIU=
-golang.org/x/tools v0.42.0 h1:uNgphsn75Tdz5Ji2q36v/nsFSfR/9BRFvqhGBaJGd5k=
-golang.org/x/tools v0.42.0/go.mod h1:Ma6lCIwGZvHK6XtgbswSoWroEkhugApmsXyrUmBhfr0=
+golang.org/x/tools v0.44.0 h1:UP4ajHPIcuMjT1GqzDWRlalUEoY+uzoZKnhOjbIPD2c=
+golang.org/x/tools v0.44.0/go.mod h1:KA0AfVErSdxRZIsOVipbv3rQhVXTnlU6UhKxHd1seDI=
 golang.org/x/xerrors v0.0.0-20190717185122-a985d3407aa7/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20240903120638-7835f813f4da h1:noIWHXmPHxILtqtCOPIhSt0ABwskkZKjD3bXGnZGpNY=
 golang.org/x/xerrors v0.0.0-20240903120638-7835f813f4da/go.mod h1:NDW/Ps6MPRej6fsCIbMTohpP40sJ/P/vI1MoTEGwX90=
-google.golang.org/genproto v0.0.0-20260217215200-42d3e9bedb6d h1:vsOm753cOAMkt76efriTCDKjpCbK18XGHMJHo0JUKhc=
-google.golang.org/genproto v0.0.0-20260217215200-42d3e9bedb6d/go.mod h1:0oz9d7g9QLSdv9/lgbIjowW1JoxMbxmBVNe8i6tORJI=
-google.golang.org/genproto/googleapis/api v0.0.0-20260217215200-42d3e9bedb6d h1:EocjzKLywydp5uZ5tJ79iP6Q0UjDnyiHkGRWxuPBP8s=
-google.golang.org/genproto/googleapis/api v0.0.0-20260217215200-42d3e9bedb6d/go.mod h1:48U2I+QQUYhsFrg2SY6r+nJzeOtjey7j//WBESw+qyQ=
-google.golang.org/genproto/googleapis/rpc v0.0.0-20260217215200-42d3e9bedb6d h1:t/LOSXPJ9R0B6fnZNyALBRfZBH0Uy0gT+uR+SJ6syqQ=
-google.golang.org/genproto/googleapis/rpc v0.0.0-20260217215200-42d3e9bedb6d/go.mod h1:4Hqkh8ycfw05ld/3BWL7rJOSfebL2Q+DVDeRgYgxUU8=
-google.golang.org/grpc v1.79.1 h1:zGhSi45ODB9/p3VAawt9a+O/MULLl9dpizzNNpq7flY=
-google.golang.org/grpc v1.79.1/go.mod h1:KmT0Kjez+0dde/v2j9vzwoAScgEPx/Bw1CYChhHLrHQ=
+google.golang.org/genproto v0.0.0-20260319201613-d00831a3d3e7 h1:XzmzkmB14QhVhgnawEVsOn6OFsnpyxNPRY9QV01dNB0=
+google.golang.org/genproto v0.0.0-20260319201613-d00831a3d3e7/go.mod h1:L43LFes82YgSonw6iTXTxXUX1OlULt4AQtkik4ULL/I=
+google.golang.org/genproto/googleapis/api v0.0.0-20260319201613-d00831a3d3e7 h1:41r6JMbpzBMen0R/4TZeeAmGXSJC7DftGINUodzTkPI=
+google.golang.org/genproto/googleapis/api v0.0.0-20260319201613-d00831a3d3e7/go.mod h1:EIQZ5bFCfRQDV4MhRle7+OgjNtZ6P1PiZBgAKuxXu/Y=
+google.golang.org/genproto/googleapis/rpc v0.0.0-20260401024825-9d38bb4040a9 h1:m8qni9SQFH0tJc1X0vmnpw/0t+AImlSvp30sEupozUg=
+google.golang.org/genproto/googleapis/rpc v0.0.0-20260401024825-9d38bb4040a9/go.mod h1:4Hqkh8ycfw05ld/3BWL7rJOSfebL2Q+DVDeRgYgxUU8=
+google.golang.org/grpc v1.80.0 h1:Xr6m2WmWZLETvUNvIUmeD5OAagMw3FiKmMlTdViWsHM=
+google.golang.org/grpc v1.80.0/go.mod h1:ho/dLnxwi3EDJA4Zghp7k2Ec1+c2jqup0bFkw07bwF4=
 google.golang.org/protobuf v1.36.11 h1:fV6ZwhNocDyBLK0dj+fg8ektcVegBBuEolpbTQyBNVE=
 google.golang.org/protobuf v1.36.11/go.mod h1:HTf+CrKn2C3g5S8VImy6tdcUvCska2kB7j23XfzDpco=
 gopkg.in/check.v1 v0.0.0-20161208181325-20d25e280405/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
diff --git a/landjail/parent.go b/landjail/parent.go
index 4cd7796..d399d3d 100644
--- a/landjail/parent.go
+++ b/landjail/parent.go
@@ -27,7 +27,7 @@ func RunParent(ctx context.Context, logger *slog.Logger, config config.AppConfig
 	ruleEngine := rulesengine.NewRuleEngine(allowRules, logger)
 
 	// Create auditor
-	auditor, err := audit.SetupAuditor(ctx, logger, config.DisableAuditLogs, config.LogProxySocketPath)
+	auditor, err := audit.SetupAuditor(ctx, logger, config.DisableAuditLogs, config.LogProxySocketPath, config.SessionID)
 	if err != nil {
 		return fmt.Errorf("failed to setup auditor: %v", err)
 	}
diff --git a/nsjail_manager/parent.go b/nsjail_manager/parent.go
index 10554bf..e5d769b 100644
--- a/nsjail_manager/parent.go
+++ b/nsjail_manager/parent.go
@@ -28,7 +28,7 @@ func RunParent(ctx context.Context, logger *slog.Logger, config config.AppConfig
 	ruleEngine := rulesengine.NewRuleEngine(allowRules, logger)
 
 	// Create auditor
-	auditor, err := audit.SetupAuditor(ctx, logger, config.DisableAuditLogs, config.LogProxySocketPath)
+	auditor, err := audit.SetupAuditor(ctx, logger, config.DisableAuditLogs, config.LogProxySocketPath, config.SessionID)
 	if err != nil {
 		return fmt.Errorf("failed to setup auditor: %v", err)
 	}
diff --git a/run/run_linux.go b/run/run_linux.go
index f67d82b..5344e79 100644
--- a/run/run_linux.go
+++ b/run/run_linux.go
@@ -10,9 +10,13 @@ import (
 	"github.com/coder/boundary/config"
 	"github.com/coder/boundary/landjail"
 	"github.com/coder/boundary/nsjail_manager"
+	"github.com/google/uuid"
 )
 
 func Run(ctx context.Context, logger *slog.Logger, cfg config.AppConfig) error {
+	cfg.SessionID = uuid.New()
+	logger.Info("boundary session started", "session_id", cfg.SessionID.String())
+
 	switch cfg.JailType {
 	case config.NSJailType:
 		return nsjail_manager.Run(ctx, logger, cfg)