Identify built-in generation preparation failures

internal/usecase/prepared_execution_test.go

@@ -498,7 +498,7 @@ func TestRunnerRunPreparedReleasesAdmissionAcrossExecutionErrors(t *testing.T) {
 				}},
 			},
 			repairer:   &fakeRepairer{err: repairInvalidRequest},
-			wantError:  ErrInvalidRequest,
+			wantError:  ErrLLMGenerate,
 			wantSource: repairInvalidRequest,
 		},
 		{

internal/usecase/runner.go

@@ -18,6 +18,7 @@ import (
 	"go.maximumdirect.net/promptkit/internal/capacity"
 	"go.maximumdirect.net/promptkit/internal/defaults"
 	"go.maximumdirect.net/promptkit/internal/domain"
+	"go.maximumdirect.net/promptkit/internal/generation"
 	"go.maximumdirect.net/promptkit/internal/jsonvalue"
 	"go.maximumdirect.net/promptkit/internal/llm"
 	"go.maximumdirect.net/promptkit/internal/observation"
@@ -269,6 +270,9 @@ func (r *Runner) executePreparedRun(
 }
 
 func wrapGenerationError(err error) error {
+	if _, ok := err.(*generation.PreparationError); ok {
+		return &OperationError{Category: ErrInvalidRequest, Cause: err}
+	}
 	return &OperationError{Category: ErrLLMGenerate, Cause: err}
 }
 

internal/usecase/runner_test.go

@@ -2074,7 +2074,7 @@ func TestRunnerRunCancellationPreservesGenerationCategory(t *testing.T) {
 	}
 }
 
-func TestRunnerRunLLMInvalidRequestMapsToUsecaseInvalidRequest(t *testing.T) {
+func TestRunnerRunInjectedInvalidRequestRemainsGenerationFailure(t *testing.T) {
 	runner := NewRunner(
 		&fakePromptRepo{def: promptDef(domain.FormatText, domain.ValidationNone, 0)},
 		&fakeExecutionProfileRepo{profiles: map[string]*domain.ExecutionProfile{"exec": defaultExecutionProfile()}},
@@ -2089,11 +2089,8 @@ func TestRunnerRunLLMInvalidRequestMapsToUsecaseInvalidRequest(t *testing.T) {
 		ProfileID: "exec",
 		Inputs:    singleInputRef(),
 	})
-	if !errors.Is(err, ErrInvalidRequest) {
-		t.Fatalf("expected ErrInvalidRequest, got %v", err)
-	}
-	if errors.Is(err, ErrLLMGenerate) {
-		t.Fatalf("did not expect ErrLLMGenerate, got %v", err)
+	if !errors.Is(err, ErrLLMGenerate) || !errors.Is(err, llm.ErrInvalidRequest) {
+		t.Fatalf("expected generation error retaining cause, got %v", err)
 	}
 }
 

internal/usecase/smoke_tester.go

@@ -210,6 +210,9 @@ func (t *SmokeTester) runInference(
 		report.Failure = generation.ClassifyFailure(contextErr)
 		return finish(contextErr)
 	}
+	if evidence.PreparationFailed && generationErr != nil {
+		return nil, &OperationError{Category: ErrInvalidRequest, Cause: generationErr}
+	}
 	if generationErr != nil {
 		report.Failure = generation.ClassifyFailure(generationErr)
 		report.Completed = true