fix: prevent question card loop when agent mentions keywords as context

- Add finish category to _is_category_satisfied (checks constraints for
surface finish entries)
- Add anti-loop protection: skip cards for categories whose keywords
appear in the user's current message (they just answered it)
- Pass user_message through to generate_question_cards in both crew and
fallback paths

Fixes: CNC agent mentioning "surface finish" and "Ra" in NOT READY
context text caused the gap analyzer to repeatedly show a finish card
even after the user answered it.

Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>

agents/crew_orchestrator.py

@@ -408,7 +408,7 @@ class CrewOrchestrator(BaseOrchestrator):
         gap_result = analyze_gaps(responses)
         question_cards = []
         if gap_result.has_gaps:
-            cards = generate_question_cards(gap_result, updated_state)
+            cards = generate_question_cards(gap_result, updated_state, user_message=message)
             question_cards = [c.model_dump() for c in cards]
 
         # Auto-trigger plan if score crosses threshold
@@ -461,7 +461,7 @@ class CrewOrchestrator(BaseOrchestrator):
             gap_result = analyze_gaps(result_responses)
             if gap_result.has_gaps:
                 state = DesignState(**(design_state or {}))
-                cards = generate_question_cards(gap_result, state)
+                cards = generate_question_cards(gap_result, state, user_message=message)
                 result["question_cards"] = [c.model_dump() for c in cards]
             else:
                 result["question_cards"] = []

agents/gap_analyzer.py

@@ -145,14 +145,37 @@ def _is_category_satisfied(category: str, state) -> bool:
         return bool(state.constraints)
     if category == "machining":
         return bool(state.axis_recommendation)
+    if category == "finish":
+        return any("surface finish" in c.lower() or "ra " in c.lower() for c in (state.constraints or []))
     return False
 
 
-def generate_question_cards(gaps: GapAnalysis, state) -> list[QuestionCard]:
+def _is_category_in_user_message(category: str, user_message: str) -> bool:
+    """Return True if the user's current message already answers this category.
+
+    Prevents re-showing cards for categories the user just responded to.
+    """
+    if not user_message:
+        return False
+    lower = user_message.lower()
+    keywords = settings.gap_analysis.category_keywords.get(category, [])
+    return any(kw.lower() in lower for kw in keywords)
+
+
+def generate_question_cards(
+    gaps: GapAnalysis,
+    state,
+    user_message: str = "",
+) -> list[QuestionCard]:
     """Convert a GapAnalysis into question cards, skipping already-satisfied categories.
 
     Looks up responsible agent from settings, agent metadata from AGENTS dict,
     and question text/suggestions from QUESTION_TEMPLATES.
+
+    Args:
+        gaps: Result of analyze_gaps().
+        state: Current DesignState to filter against.
+        user_message: The user's current message — skips categories the user just answered.
     """
     if not gaps.has_gaps:
         return []
@@ -167,6 +190,10 @@ def generate_question_cards(gaps: GapAnalysis, state) -> list[QuestionCard]:
         if _is_category_satisfied(category, state):
             continue
 
+        # Skip if the user just answered this category (anti-loop)
+        if _is_category_in_user_message(category, user_message):
+            continue
+
         # Look up responsible agent id
         responsible_agent = category_agents.get(category, item.agent_id)
 

tests/test_gap_analyzer.py

@@ -132,6 +132,41 @@ class TestGenerateQuestionCards:
         assert cards[0].agent_name == "CNC Agent"
         assert cards[0].agent_color == "#00e676"
 
+    def test_finish_satisfied_by_constraint(self):
+        gaps = GapAnalysis(
+            has_gaps=True,
+            missing_items=[
+                MissingItem(category="finish", description="surface finish", agent_id="cnc"),
+            ],
+        )
+        state = DesignState(constraints=["surface finish: Standard"])
+        cards = generate_question_cards(gaps, state)
+        assert len(cards) == 0
+
+    def test_anti_loop_skips_category_user_just_answered(self):
+        gaps = GapAnalysis(
+            has_gaps=True,
+            missing_items=[
+                MissingItem(category="finish", description="surface finish", agent_id="cnc"),
+                MissingItem(category="dimension", description="width", agent_id="cad"),
+            ],
+        )
+        cards = generate_question_cards(gaps, DesignState(), user_message="Standard surface finish")
+        categories = [c.category for c in cards]
+        assert "finish" not in categories
+        assert "dimension" in categories
+
+    def test_anti_loop_no_effect_on_unrelated_message(self):
+        gaps = GapAnalysis(
+            has_gaps=True,
+            missing_items=[
+                MissingItem(category="material", description="material", agent_id="cad"),
+            ],
+        )
+        cards = generate_question_cards(gaps, DesignState(), user_message="make it bigger")
+        assert len(cards) == 1
+        assert cards[0].category == "material"
+
     def test_model_category_no_suggestions(self):
         gaps = GapAnalysis(
             has_gaps=True,