diff --git a/main.go b/main.go
index e14ae1b..27f8d0c 100644
--- a/main.go
+++ b/main.go
@@ -1153,22 +1153,31 @@ func publishWatchReadiness(path string, readinessErr error) error {
 
 func waitWatchReadiness(path string, timeout time.Duration) error {
 	deadline := time.Now().Add(timeout)
+	// A readiness file that does not parse is a file still being written, not
+	// a daemon that failed: publishWatchReadiness renames its payload into
+	// place atomically, but nothing guarantees every writer does, and treating
+	// the first unparseable read as fatal reported a startup failure for a
+	// daemon that was starting fine. Keep the last parse error so a file that
+	// never becomes valid says why, rather than only that it timed out.
+	var lastParseErr error
 	for {
 		data, err := os.ReadFile(path)
 		if err == nil {
 			var status watchReadiness
-			if err := json.Unmarshal(data, &status); err != nil {
-				return fmt.Errorf("reading daemon readiness: %w", err)
-			}
-			if status.Error != "" {
+			if parseErr := json.Unmarshal(data, &status); parseErr != nil {
+				lastParseErr = parseErr
+			} else if status.Error != "" {
 				return errors.New(status.Error)
+			} else {
+				return nil
 			}
-			return nil
-		}
-		if !errors.Is(err, os.ErrNotExist) {
+		} else if !errors.Is(err, os.ErrNotExist) {
 			return fmt.Errorf("reading daemon readiness: %w", err)
 		}
 		if time.Now().After(deadline) {
+			if lastParseErr != nil {
+				return fmt.Errorf("reading daemon readiness: %w", lastParseErr)
+			}
 			return fmt.Errorf("daemon readiness timed out after %s", timeout)
 		}
 		time.Sleep(10 * time.Millisecond)
diff --git a/watch_readiness_test.go b/watch_readiness_test.go
new file mode 100644
index 0000000..e2a10cb
--- /dev/null
+++ b/watch_readiness_test.go
@@ -0,0 +1,66 @@
+package main
+
+import (
+	"os"
+	"path/filepath"
+	"strings"
+	"testing"
+	"time"
+)
+
+// A readiness file caught mid-write reads as zero or partial bytes. Treating
+// that as fatal reported a startup failure for a daemon that was starting
+// fine, and made TestRunWatchStartWaitsForChildReadinessFailure fail whenever
+// the machine was loaded enough to land in the window.
+func TestWaitWatchReadinessWaitsThroughPartialWrite(t *testing.T) {
+	path := filepath.Join(t.TempDir(), "ready.json")
+	if err := os.WriteFile(path, nil, 0o644); err != nil {
+		t.Fatal(err)
+	}
+	go func() {
+		time.Sleep(50 * time.Millisecond)
+		_ = os.WriteFile(path, []byte(`{"error":"claim rejected"}`), 0o644)
+	}()
+
+	err := waitWatchReadiness(path, 5*time.Second)
+	if err == nil || !strings.Contains(err.Error(), "claim rejected") {
+		t.Fatalf("waitWatchReadiness() = %v, want the daemon's own error once the file is complete", err)
+	}
+}
+
+func TestWaitWatchReadinessSucceedsAfterPartialWrite(t *testing.T) {
+	path := filepath.Join(t.TempDir(), "ready.json")
+	if err := os.WriteFile(path, []byte(`{"err`), 0o644); err != nil {
+		t.Fatal(err)
+	}
+	go func() {
+		time.Sleep(50 * time.Millisecond)
+		_ = os.WriteFile(path, []byte(`{}`), 0o644)
+	}()
+
+	if err := waitWatchReadiness(path, 5*time.Second); err != nil {
+		t.Fatalf("waitWatchReadiness() = %v, want success once the file is complete", err)
+	}
+}
+
+// A file that never becomes valid still has to say why, rather than reporting
+// only that it timed out.
+func TestWaitWatchReadinessReportsPersistentGarbage(t *testing.T) {
+	path := filepath.Join(t.TempDir(), "ready.json")
+	if err := os.WriteFile(path, []byte("not json at all"), 0o644); err != nil {
+		t.Fatal(err)
+	}
+	err := waitWatchReadiness(path, 200*time.Millisecond)
+	if err == nil || !strings.Contains(err.Error(), "reading daemon readiness") {
+		t.Fatalf("waitWatchReadiness() = %v, want the parse failure surfaced", err)
+	}
+}
+
+// A missing file must still time out rather than hang.
+func TestWaitWatchReadinessTimesOutWhenAbsent(t *testing.T) {
+	path := filepath.Join(t.TempDir(), "never-written.json")
+	err := waitWatchReadiness(path, 100*time.Millisecond)
+	if err == nil || !strings.Contains(err.Error(), "timed out") {
+		t.Fatalf("waitWatchReadiness() = %v, want a timeout", err)
+	}
+}