Run bounded output repair attempts

internal/usecase/runner.go

@@ -184,10 +184,10 @@ func (r *Runner) executePreparedRun(
 		prepared.StructuredOutput,
 	))
 	if err != nil {
-		if errors.Is(err, llm.ErrInvalidRequest) {
-			return nil, fmt.Errorf("%w: %w", ErrInvalidRequest, err)
-		}
-		return nil, fmt.Errorf("%w: %w", ErrLLMGenerate, err)
+		return nil, wrapGenerationError(err)
+	}
+	if genResp == nil {
+		return nil, fmt.Errorf("%w: model returned nil response", ErrLLMGenerate)
 	}
 	usage := genResp.Usage
 
@@ -203,6 +203,7 @@ func (r *Runner) executePreparedRun(
 			attemptsUsed++
 
 			repairResp, repairErr := r.repairer.Repair(ctx, RepairRequest{
+				OriginalMessages: prepared.Messages,
 				PreviousOutput:   genResp.Content,
 				ValidationErrors: validationResult.Errors,
 				SessionID:        prepared.SessionID,
@@ -214,10 +215,10 @@ func (r *Runner) executePreparedRun(
 				Mode:             prepared.OutputContract.ValidationMode,
 			})
 			if repairErr != nil {
-				return nil, fmt.Errorf("%w: %w", ErrValidation, repairErr)
+				return nil, wrapGenerationError(repairErr)
 			}
 			if repairResp == nil {
-				return nil, fmt.Errorf("%w: repairer returned nil response", ErrValidation)
+				return nil, fmt.Errorf("%w: repairer returned nil response", ErrLLMGenerate)
 			}
 
 			genResp = repairResp
@@ -257,6 +258,13 @@ func (r *Runner) executePreparedRun(
 	}, nil
 }
 
+func wrapGenerationError(err error) error {
+	if errors.Is(err, llm.ErrInvalidRequest) {
+		return fmt.Errorf("%w: %w", ErrInvalidRequest, err)
+	}
+	return fmt.Errorf("%w: %w", ErrLLMGenerate, err)
+}
+
 func addTokenUsage(total, next domain.TokenUsage) domain.TokenUsage {
 	return domain.TokenUsage{
 		PromptTokens:     total.PromptTokens + next.PromptTokens,
@@ -524,7 +532,12 @@ func (r *Runner) shouldAttemptRepair(contract domain.OutputContract, validationR
 	if validationResult.Status != domain.ValidationFailed {
 		return false
 	}
-	return contract.ValidationMode == domain.ValidationJSON || contract.ValidationMode == domain.ValidationJSONSchema
+	switch contract.ValidationMode {
+	case domain.ValidationBasic, domain.ValidationJSON, domain.ValidationJSONSchema:
+		return true
+	default:
+		return false
+	}
 }
 
 func mergeExecutionTarget(base domain.ExecutionTarget, override domain.ExecutionTarget) domain.ExecutionTarget {