feat(task-023): improve generated context quality

tests/test_generate_context.py

@@ -292,6 +292,7 @@ class TestIntegration:
         assert "context/product-brief.md" in result["generated"]
         assert "context/project-brief.md" in result["generated"]
         assert "context/risks.md" in result["generated"]
+        assert "context/company-context.md" in result["generated"]  # Q-002 → company-context
         assert "context/assumptions.md" not in result["generated"]  # Q-008 is Low confidence
 
         # Check that product-brief has filled sections
@@ -299,6 +300,11 @@ class TestIntegration:
         assert "CLI tool for discovery workflow" in content
         assert "Internal developers and small dev teams" in content
 
+        # Check company-context got users data from Q-002
+        company = (tmp_project / "context/company-context.md").read_text()
+        assert "## Customers / Users" in company
+        assert "Internal developers and small dev teams" in company
+
         # Check that risks.md got a table row
         risks = (tmp_project / "context/risks.md").read_text()
         assert "| RISK-007 |" in risks
@@ -314,3 +320,140 @@ class TestIntegration:
 
         result = (tmp_project / "context/infrastructure-context.md").read_text()
         assert "Cloud provider details" in result  # Original content preserved
+
+
+class TestContextQuality:
+    """Tests for TASK-023: improved context generation quality."""
+
+    def test_company_context_populated_from_users(self):
+        """company-context.md should be populated when discovery answers include users/stakeholders."""
+        from pathlib import Path
+        import tempfile
+        import shutil
+
+        tmp_path = Path(tempfile.mkdtemp())
+        root = tmp_path / "testproject"
+        root.mkdir()
+        (root / "context").mkdir()
+
+        # Only Q-002 (users) - no other discovery data
+        (root / "context" / "discovery-log.md").write_text(
+            "# Discovery Log\n\n"
+            "| ID | Question | Answer | Confidence | Follow-up needed | Linked decision | Linked task | Date |\n"
+            "|---|---|---|---|---|---|---|---|\n"
+            '| Q-002 | Who is the user? | Internal dev teams and external customers | High | No |  |  | 2026-06-03 |\n',
+            encoding="utf-8",
+        )
+
+        from rdb_discovery.generate_context import generate_context_files
+
+        result = generate_context_files(root)
+        assert "context/company-context.md" in result["generated"]
+        assert "context/product-brief.md" in result["generated"]
+
+        company = (root / "context/company-context.md").read_text()
+        assert "## Customers / Users" in company
+        assert "Internal dev teams and external customers" in company
+
+        shutil.rmtree(tmp_path)
+
+    def test_agent_guidelines_gets_testing_preferences(self):
+        """agent-guidelines.md should get Testing Preferences from testing discovery answers."""
+        from pathlib import Path
+        import tempfile
+        import shutil
+
+        tmp_path = Path(tempfile.mkdtemp())
+        root = tmp_path / "testproject"
+        root.mkdir()
+        (root / "context").mkdir()
+
+        # Only Q-009 (testing) - no agent tooling questions
+        (root / "context" / "discovery-log.md").write_text(
+            "# Discovery Log\n\n"
+            "| ID | Question | Answer | Confidence | Follow-up needed | Linked decision | Linked task | Date |\n"
+            "|---|---|---|---|---|---|---|---|\n"
+            '| Q-009 | How will we test it? | pytest with coverage, integration tests via docker-compose | Medium | No |  |  | 2026-06-03 |\n',
+            encoding="utf-8",
+        )
+
+        from rdb_discovery.generate_context import generate_context_files
+
+        result = generate_context_files(root)
+        assert "context/agent-guidelines.md" in result["generated"]
+
+        guidelines = (root / "context/agent-guidelines.md").read_text()
+        assert "## Testing Preferences" in guidelines
+        assert "pytest with coverage" in guidelines
+
+        shutil.rmtree(tmp_path)
+
+    def test_no_testing_answers_in_timeline(self):
+        """Testing answers must not be mapped to Timeline & Milestones sections."""
+        from pathlib import Path
+        import tempfile
+        import shutil
+
+        tmp_path = Path(tempfile.mkdtemp())
+        root = tmp_path / "testproject"
+        root.mkdir()
+        (root / "context").mkdir()
+
+        # Only Q-009 (testing) - verify no timeline data appears
+        (root / "context" / "discovery-log.md").write_text(
+            "# Discovery Log\n\n"
+            "| ID | Question | Answer | Confidence | Follow-up needed | Linked decision | Linked task | Date |\n"
+            "|---|---|---|---|---|---|---|\n"
+            '| Q-009 | How will we test it? | pytest with coverage | High | No |  |  | 2026-06-03 |\n',
+            encoding="utf-8",
+        )
+
+        # Create project-brief.md that has a Timeline section already
+        (root / "context" / "project-brief.md").write_text(
+            "# Project Brief\n\n## Timeline & Milestones\n\nTBD\n",
+            encoding="utf-8",
+        )
+
+        from rdb_discovery.generate_context import generate_context_files
+
+        result = generate_context_files(root)
+        assert "context/project-brief.md" not in result["generated"]
+
+        timeline_content = (root / "context/project-brief.md").read_text()
+        # The Timeline section should remain as TBD (not filled with testing data)
+        assert "pytest with coverage" not in timeline_content
+        # Original TBD placeholder preserved
+        assert "TBD" in timeline_content
+
+        shutil.rmtree(tmp_path)
+
+    def test_repository_context_populated_from_dependencies(self):
+        """repository-context.md should be populated when answers include dependencies."""
+        from pathlib import Path
+        import tempfile
+        import shutil
+
+        tmp_path = Path(tempfile.mkdtemp())
+        root = tmp_path / "testproject"
+        root.mkdir()
+        (root / "context").mkdir()
+
+        # Q-012 includes technology stack info that maps to repository dependencies
+        (root / "context" / "discovery-log.md").write_text(
+            "# Discovery Log\n\n"
+            "| ID | Question | Answer | Confidence | Follow-up needed | Linked decision | Linked task | Date |\n"
+            "|---|---|---|---|---|---|---|---|\n"
+            '| Q-012 | What is the technology stack, repository structure, and architecture approach? | Python 3.12, Typer, Rich; Docker; PostgreSQL | High | No |  |  | 2026-06-03 |\n',
+            encoding="utf-8",
+        )
+
+        from rdb_discovery.generate_context import generate_context_files
+
+        result = generate_context_files(root)
+        assert "context/repository-context.md" in result["generated"]
+
+        repo_ctx = (root / "context/repository-context.md").read_text()
+        assert "## Dependencies" in repo_ctx
+        assert "Python 3.12, Typer, Rich" in repo_ctx
+
+        shutil.rmtree(tmp_path)