From bba267645d2d7095fcebe84e3021ebca9b2e98ce Mon Sep 17 00:00:00 2001
From: Michael Suchacz <203725896+ibetitsmike@users.noreply.github.com>
Date: Thu, 23 Jul 2026 23:10:11 +0000
Subject: [PATCH] fix(coderd/x/chatd/chatloop): surface reasoning-only
 content-filter refusals as terminal errors

---
 coderd/x/chatd/chatloop/chatloop.go           | 24 ++++++++++--
 .../chatloop/contentfilter_internal_test.go   | 39 +++++++++++++++++++
 2 files changed, 59 insertions(+), 4 deletions(-)

diff --git a/coderd/x/chatd/chatloop/chatloop.go b/coderd/x/chatd/chatloop/chatloop.go
index ff659f1021a68..bb46e3f27686b 100644
--- a/coderd/x/chatd/chatloop/chatloop.go
+++ b/coderd/x/chatd/chatloop/chatloop.go
@@ -439,10 +439,12 @@ func GenerateAssistant(ctx context.Context, opts GenerateAssistantOptions) (Assi
 		ctx, opts.Logger, provider, modelName,
 		"assistant_helper", 0, result.finishReason, result.content,
 	)
-	// A content-filter finish with no content means the provider's
-	// safety classifiers blocked the whole response (e.g. Anthropic
-	// stop_reason "refusal").
-	if len(result.content) == 0 && result.finishReason == fantasy.FinishReasonContentFilter {
+	// A content-filter finish without user-visible output means the
+	// provider's safety classifiers blocked the whole response (e.g.
+	// Anthropic stop_reason "refusal"). The refusal can arrive after
+	// reasoning has already streamed, so reasoning alone must not
+	// count as output.
+	if result.finishReason == fantasy.FinishReasonContentFilter && !hasUserVisibleContent(result.content) {
 		return AssistantOutcome{}, contentFilterError(errorProvider, result.providerMetadata)
 	}
 	step := PersistedStep{
@@ -479,6 +481,20 @@ func wrapProviderStreamError(provider string, err error) error {
 	return xerrors.Errorf("stream response: %w", chaterror.WithClassification(err, classified))
 }
 
+// hasUserVisibleContent reports whether any content part carries output the
+// user can see. Reasoning parts do not count: they stream transiently and are
+// not a substitute for a response.
+func hasUserVisibleContent(content []fantasy.Content) bool {
+	for _, part := range content {
+		switch part.(type) {
+		case fantasy.ReasoningContent, *fantasy.ReasoningContent:
+		default:
+			return true
+		}
+	}
+	return false
+}
+
 func contentFilterError(provider string, metadata fantasy.ProviderMetadata) error {
 	classified := chaterror.ClassifiedError{
 		Kind:      codersdk.ChatErrorKindContentFilter,
diff --git a/coderd/x/chatd/chatloop/contentfilter_internal_test.go b/coderd/x/chatd/chatloop/contentfilter_internal_test.go
index db7b571addc61..a57aca48b1cd4 100644
--- a/coderd/x/chatd/chatloop/contentfilter_internal_test.go
+++ b/coderd/x/chatd/chatloop/contentfilter_internal_test.go
@@ -120,6 +120,45 @@ func TestGenerateAssistant_ContentFilterRefusal(t *testing.T) {
 		require.Equal(t, "The response was blocked.", classified.Detail)
 	})
 
+	t.Run("ReasoningOnlyContentSurfacesTerminalError", func(t *testing.T) {
+		t.Parallel()
+
+		model := &chattest.FakeModel{
+			ProviderName: "anthropic",
+			ModelName:    "test-model",
+			StreamFn: func(_ context.Context, _ fantasy.Call) (fantasy.StreamResponse, error) {
+				return streamFromParts([]fantasy.StreamPart{
+					{Type: fantasy.StreamPartTypeReasoningStart, ID: "reasoning-1"},
+					{Type: fantasy.StreamPartTypeReasoningDelta, ID: "reasoning-1", Delta: "planning next steps"},
+					{Type: fantasy.StreamPartTypeReasoningEnd, ID: "reasoning-1"},
+					{
+						Type:         fantasy.StreamPartTypeFinish,
+						FinishReason: fantasy.FinishReasonContentFilter,
+						ProviderMetadata: refusalProviderMetadataForTest(
+							"harmful_content", "The response was blocked.",
+						),
+					},
+				}), nil
+			},
+		}
+
+		outcome, err := GenerateAssistant(context.Background(), GenerateAssistantOptions{
+			Model: model,
+			Messages: []fantasy.Message{
+				textMessage(fantasy.MessageRoleUser, "hello"),
+			},
+		})
+		require.ErrorIs(t, err, ErrContentFiltered)
+		require.Empty(t, outcome.Step.Content)
+
+		classified := chaterror.Classify(err)
+		require.Equal(t, codersdk.ChatErrorKindContentFilter, classified.Kind)
+		require.Equal(t, "anthropic", classified.Provider)
+		require.False(t, classified.Retryable)
+		require.Equal(t, "Anthropic blocked this response under its content policy (harmful_content).", classified.Message)
+		require.Equal(t, "The response was blocked.", classified.Detail)
+	})
+
 	t.Run("PartialContentIsPersistedNotErrored", func(t *testing.T) {
 		t.Parallel()