diff --git a/worker/internal/worker/worker.go b/worker/internal/worker/worker.go
index cd17c90..ce0ad13 100644
--- a/worker/internal/worker/worker.go
+++ b/worker/internal/worker/worker.go
@@ -177,17 +177,12 @@ func Run(ctx context.Context, config Config, payload Payload, publisher Publishe
 				defer close(watcherDone)
 				select {
 				case <-workContext.Done():
-					_ = syscall.Kill(-command.Process.Pid, syscall.SIGTERM)
-					timer := time.NewTimer(config.GracePeriod)
-					defer timer.Stop()
-					select {
-					case <-timer.C:
-						_ = syscall.Kill(-command.Process.Pid, syscall.SIGKILL)
-					case <-processDone:
-						// Descendants may have survived the shell's termination.
-						_ = syscall.Kill(-command.Process.Pid, syscall.SIGKILL)
-					}
+					terminateProcessGroup(command.Process.Pid, config.GracePeriod)
 				case <-processDone:
+					if workContext.Err() != nil {
+						terminateProcessGroup(command.Process.Pid, config.GracePeriod)
+						return
+					}
 					_ = syscall.Kill(-command.Process.Pid, syscall.SIGKILL)
 				}
 			}()
@@ -234,6 +229,27 @@ func Run(ctx context.Context, config Config, payload Payload, publisher Publishe
 	return code, errors.Join(runError, outputError)
 }
 
+// terminateProcessGroup gives surviving descendants their grace period even when
+// the leader has exited. Return early only when the entire process group is gone.
+func terminateProcessGroup(pid int, grace time.Duration) {
+	_ = syscall.Kill(-pid, syscall.SIGTERM)
+	deadline := time.NewTimer(grace)
+	defer deadline.Stop()
+	poll := time.NewTicker(10 * time.Millisecond)
+	defer poll.Stop()
+	for {
+		if errors.Is(syscall.Kill(-pid, 0), syscall.ESRCH) {
+			return
+		}
+		select {
+		case <-deadline.C:
+			_ = syscall.Kill(-pid, syscall.SIGKILL)
+			return
+		case <-poll.C:
+		}
+	}
+}
+
 // resolveHome uses the node's NSS lookup for site accounts (LDAP/SSSD).
 // A static Go binary cannot rely on user.Current or libc's user lookup.
 func resolveHome() (string, error) {
diff --git a/worker/internal/worker/worker_test.go b/worker/internal/worker/worker_test.go
index 46b61d4..2aef980 100644
--- a/worker/internal/worker/worker_test.go
+++ b/worker/internal/worker/worker_test.go
@@ -5,6 +5,7 @@ import (
 	"context"
 	"encoding/json"
 	"errors"
+	"fmt"
 	"io"
 	"os"
 	"path/filepath"
@@ -355,3 +356,45 @@ func TestUnicodeAcrossChunkBoundariesSurvivesJSON(t *testing.T) {
 		}
 	}
 }
+
+func TestCancellationLetsRedirectedChildFinishCleanup(t *testing.T) {
+	directory := t.TempDir()
+	marker := filepath.Join(directory, "flushed")
+	ready := filepath.Join(directory, "ready")
+	script := fmt.Sprintf(`trap 'exit 0' TERM
+/bin/bash -c 'trap "sleep 0.2; touch %s; exit" TERM; touch %s; while :; do sleep 0.01; done' >/dev/null 2>&1 &
+wait
+`, marker, ready)
+	ctx, cancel := context.WithTimeout(context.Background(), 3*time.Second)
+	defer cancel()
+	watcherDone := make(chan struct{})
+	go func() {
+		defer close(watcherDone)
+		ticker := time.NewTicker(time.Millisecond)
+		defer ticker.Stop()
+		for {
+			if _, err := os.Stat(ready); err == nil {
+				cancel()
+				return
+			}
+			select {
+			case <-ctx.Done():
+				return
+			case <-ticker.C:
+			}
+		}
+	}()
+	var out, errout bytes.Buffer
+	cfg := config(&out, &errout)
+	cfg.GracePeriod = time.Second
+	publisher := &fakePublisher{}
+	code, err := Run(ctx, cfg, Payload{Script: script}, publisher)
+	cancel()
+	<-watcherDone
+	if code != 143 || lastStatus(t, publisher) != "cancelled" {
+		t.Fatalf("code=%d err=%v", code, err)
+	}
+	if _, err := os.Stat(marker); err != nil {
+		t.Fatalf("child cleanup was interrupted before the grace period elapsed: %v", err)
+	}
+}