diff --git a/internal/llm/adapter.go b/internal/llm/adapter.go
index 0395d22..e6fa267 100644
--- a/internal/llm/adapter.go
+++ b/internal/llm/adapter.go
@@ -7,6 +7,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"io"
 	"regexp"
 	"strings"
 	"unicode/utf8"
@@ -206,7 +207,11 @@ func (e *StructuredValidationError) Error() string {
 	if len(e.Attempts) > 1 && e.Attempts[1].DecodeError != nil {
 		second = e.Attempts[1].DecodeError.Error()
 	}
-	return fmt.Sprintf("%s: first: %s; second: %s", ErrStructuredOutputInvalidAfterRetry, first, second)
+	msg := fmt.Sprintf("%s: first: %s; second: %s", ErrStructuredOutputInvalidAfterRetry, first, second)
+	if len(e.Attempts) > 2 && e.Attempts[2].DecodeError != nil {
+		msg += fmt.Sprintf("; third: %s", e.Attempts[2].DecodeError.Error())
+	}
+	return msg
 }
 
 // Is matches ErrStructuredOutputInvalidAfterRetry for errors.Is callers.
@@ -255,16 +260,56 @@ func RunStructuredWithSessionResume[T any](ctx context.Context, adapter Adapter,
 		return StructuredResult[T]{Response: retryResponse, SessionID: retrySessionID, ValidationAttempts: attempts}, err
 	}
 	retryValue, retryAcceptedOutput, retryErr := decodeStructuredAccepted(decode, retryResponse.StructuredOutput)
-	if retryErr != nil {
+	if retryErr == nil {
+		return StructuredResult[T]{Value: retryValue, Response: retryResponse, SessionID: retrySessionID, ValidationAttempts: attempts, AcceptedOutput: retryAcceptedOutput}, nil
+	}
+	attempts = append(attempts, StructuredValidationAttempt{
+		Label:       "retry",
+		SessionID:   retrySessionID,
+		Response:    cloneResponse(retryResponse),
+		DecodeError: retryErr,
+	})
+
+	// A truncated retry never finished, so the "invalid JSON" prompt can't fix
+	// it; give it one more attempt instead of failing the task.
+	if !isTruncatedStructuredOutput(retryErr) {
+		return StructuredResult[T]{Value: zero, Response: retryResponse, SessionID: retrySessionID, ValidationAttempts: attempts}, &StructuredValidationError{Attempts: attempts}
+	}
+	secondRetryReq := retryReq
+	if secondRetryReq.OnValidationRetry != nil {
+		if err := secondRetryReq.OnValidationRetry(&secondRetryReq); err != nil {
+			return StructuredResult[T]{Response: retryResponse, SessionID: retrySessionID, ValidationAttempts: attempts}, err
+		}
+	}
+	secondRetryReq.Prompt = retryPrompt(req.Prompt, retryErr)
+	secondRetryResumeSessionID := ""
+	if !secondRetryReq.FreshValidationRetrySession {
+		secondRetryResumeSessionID = retrySessionID
+	}
+	if strings.TrimSpace(secondRetryResumeSessionID) == "" && !secondRetryReq.FreshValidationRetrySession {
+		secondRetryResumeSessionID = resumeSessionID
+	}
+	secondRetrySessionID, secondRetryResponse, err := runOnceWithSession(ctx, adapter, secondRetryResumeSessionID, secondRetryReq)
+	if err != nil {
+		return StructuredResult[T]{Response: secondRetryResponse, SessionID: secondRetrySessionID, ValidationAttempts: attempts}, err
+	}
+	secondRetryValue, secondRetryAcceptedOutput, secondRetryErr := decodeStructuredAccepted(decode, secondRetryResponse.StructuredOutput)
+	if secondRetryErr != nil {
 		attempts = append(attempts, StructuredValidationAttempt{
-			Label:       "retry",
-			SessionID:   retrySessionID,
-			Response:    cloneResponse(retryResponse),
-			DecodeError: retryErr,
+			Label:       "retry_2",
+			SessionID:   secondRetrySessionID,
+			Response:    cloneResponse(secondRetryResponse),
+			DecodeError: secondRetryErr,
 		})
-		return StructuredResult[T]{Value: zero, Response: retryResponse, SessionID: retrySessionID, ValidationAttempts: attempts}, &StructuredValidationError{Attempts: attempts}
+		return StructuredResult[T]{Value: zero, Response: secondRetryResponse, SessionID: secondRetrySessionID, ValidationAttempts: attempts}, &StructuredValidationError{Attempts: attempts}
 	}
-	return StructuredResult[T]{Value: retryValue, Response: retryResponse, SessionID: retrySessionID, ValidationAttempts: attempts, AcceptedOutput: retryAcceptedOutput}, nil
+	return StructuredResult[T]{Value: secondRetryValue, Response: secondRetryResponse, SessionID: secondRetrySessionID, ValidationAttempts: attempts, AcceptedOutput: secondRetryAcceptedOutput}, nil
+}
+
+// isTruncatedStructuredOutput reports whether decoding stopped before a
+// complete JSON value: io.EOF when empty, io.ErrUnexpectedEOF when cut off.
+func isTruncatedStructuredOutput(err error) bool {
+	return errors.Is(err, io.ErrUnexpectedEOF) || errors.Is(err, io.EOF)
 }
 
 // decodeStructuredAccepted strict-decodes data, then on failure recovers a
diff --git a/internal/llm/adapter_test.go b/internal/llm/adapter_test.go
index 8e9d0fe..fd7a9a2 100644
--- a/internal/llm/adapter_test.go
+++ b/internal/llm/adapter_test.go
@@ -438,6 +438,98 @@ func assertValidationAttempts(t *testing.T, attempts []StructuredValidationAttem
 	}
 }
 
+func TestRunStructuredTruncatedResponseGetsExtraAttempt(t *testing.T) {
+	type probe struct {
+		OK bool `json:"ok"`
+	}
+	decodeProbe := func(data []byte) (probe, error) {
+		var p probe
+		if err := json.NewDecoder(bytes.NewReader(data)).Decode(&p); err != nil {
+			return probe{}, err
+		}
+		return p, nil
+	}
+
+	t.Run("recovers on a third attempt after two truncated responses", func(t *testing.T) {
+		adapter := &FakeAdapter{}
+		adapter.Queue(FakeResult{SessionID: "s1", Response: Response{StructuredOutput: []byte(`{"ok":true,"ex`)}})
+		adapter.Queue(FakeResult{SessionID: "s2", Response: Response{StructuredOutput: []byte(`{"ok":true,"ex`)}})
+		adapter.Queue(FakeResult{SessionID: "s3", Response: Response{StructuredOutput: []byte(`{"ok":true}`)}})
+
+		result, err := RunStructuredWithSessionResume(context.Background(), adapter, "", Request{Prompt: "prompt"}, decodeProbe)
+		if err != nil {
+			t.Fatalf("RunStructuredWithSessionResume: %v", err)
+		}
+		if !result.Value.OK {
+			t.Fatalf("value = %#v, want recovered object", result.Value)
+		}
+		if requests := len(adapter.Requests()); requests != 3 {
+			t.Fatalf("requests = %d, want three attempts for a repeatedly truncated response", requests)
+		}
+		if len(result.ValidationAttempts) != 2 {
+			t.Fatalf("validation attempts = %#v, want two recorded failures before recovery", result.ValidationAttempts)
+		}
+		if result.ValidationAttempts[0].Label != "initial" || result.ValidationAttempts[1].Label != "retry" {
+			t.Fatalf("validation attempt labels = %#v, want initial then retry", result.ValidationAttempts)
+		}
+		if !errors.Is(result.ValidationAttempts[0].DecodeError, io.ErrUnexpectedEOF) ||
+			!errors.Is(result.ValidationAttempts[1].DecodeError, io.ErrUnexpectedEOF) {
+			t.Fatalf("validation attempt decode errors = %#v, want unexpected EOF", result.ValidationAttempts)
+		}
+	})
+
+	t.Run("fails after three truncated attempts", func(t *testing.T) {
+		adapter := &FakeAdapter{}
+		adapter.Queue(FakeResult{SessionID: "s1", Response: Response{StructuredOutput: []byte(`{"ok":true,"ex`)}})
+		adapter.Queue(FakeResult{SessionID: "s2", Response: Response{StructuredOutput: []byte(`{"ok":true,"ex`)}})
+		adapter.Queue(FakeResult{SessionID: "s3", Response: Response{StructuredOutput: []byte(`{"ok":true,"ex`)}})
+
+		_, err := RunStructuredWithSessionResume(context.Background(), adapter, "", Request{Prompt: "prompt"}, decodeProbe)
+		if !errors.Is(err, ErrStructuredOutputInvalidAfterRetry) {
+			t.Fatalf("RunStructuredWithSessionResume error = %v, want %v", err, ErrStructuredOutputInvalidAfterRetry)
+		}
+		var validationErr *StructuredValidationError
+		if !errors.As(err, &validationErr) {
+			t.Fatalf("error type = %T, want StructuredValidationError", err)
+		}
+		if len(validationErr.Attempts) != 3 {
+			t.Fatalf("attempts = %#v, want three recorded attempts", validationErr.Attempts)
+		}
+		if validationErr.Attempts[2].Label != "retry_2" {
+			t.Fatalf("attempts[2].Label = %q, want retry_2", validationErr.Attempts[2].Label)
+		}
+		if !strings.Contains(err.Error(), "third:") {
+			t.Fatalf("error = %q, want a third summary once a third attempt ran", err.Error())
+		}
+		if requests := len(adapter.Requests()); requests != 3 {
+			t.Fatalf("requests = %d, want exactly three attempts, not unbounded retry", requests)
+		}
+	})
+
+	t.Run("does not extend a retry that fails on a genuine schema violation", func(t *testing.T) {
+		adapter := &FakeAdapter{}
+		adapter.Queue(FakeResult{SessionID: "s1", Response: Response{StructuredOutput: []byte(`{"ok":true,"ex`)}})
+		adapter.Queue(FakeResult{SessionID: "s2", Response: Response{StructuredOutput: []byte(`{"ok":false}`)}})
+
+		_, err := RunStructuredWithSessionResume(context.Background(), adapter, "", Request{Prompt: "prompt"}, func(data []byte) (probe, error) {
+			p, err := decodeProbe(data)
+			if err != nil {
+				return probe{}, err
+			}
+			if !p.OK {
+				return probe{}, errors.New("ok must be true")
+			}
+			return p, nil
+		})
+		if !errors.Is(err, ErrStructuredOutputInvalidAfterRetry) {
+			t.Fatalf("RunStructuredWithSessionResume error = %v, want %v", err, ErrStructuredOutputInvalidAfterRetry)
+		}
+		if requests := len(adapter.Requests()); requests != 2 {
+			t.Fatalf("requests = %d, want the retry budget unchanged once the response is complete-but-wrong", requests)
+		}
+	})
+}
+
 func TestRunStructuredProseRecovery(t *testing.T) {
 	type probe struct {
 		OK bool `json:"ok"`
diff --git a/internal/pipeline/pipeline_test.go b/internal/pipeline/pipeline_test.go
index af43d65..e5c92d7 100644
--- a/internal/pipeline/pipeline_test.go
+++ b/internal/pipeline/pipeline_test.go
@@ -7250,7 +7250,7 @@ func (a *reviewerIsolationAdapter) Start(_ context.Context, req llm.Request) (ll
 		if attempt > 1 {
 			sessionID = "beta-retry-session"
 		}
-		return staticStream{sessionID: sessionID, output: `{"schema_version": 1, "agent_id": "harness:beta", "findings": [`}, nil
+		return staticStream{sessionID: sessionID, output: `{"schema_version": 1, "agent_id": "harness:beta", "findings": []}`}, nil
 	case strings.Contains(req.Prompt, `"id": "harness:gamma"`):
 		a.waitReviewerStart("harness:gamma")
 		return staticStream{sessionID: "gamma-session", output: findingsJSON("harness:gamma", "main.go", "minor", 2, "gamma finding")}, nil