FIX: Sync docs TOC with generated API pages + fail-fast TOC validation

build_scripts/gen_api_md.py

@@ -17,8 +17,13 @@
 """
 
 import json
+import sys
 from pathlib import Path
 
+# Import sibling script for post-generation TOC validation.
+sys.path.insert(0, str(Path(__file__).parent))
+import validate_docs  # noqa: E402
+
 API_JSON_DIR = Path("doc/_api")
 API_MD_DIR = Path("doc/api")
 
@@ -399,6 +404,15 @@ def main() -> None:
     index_path.write_text("\n".join(index_parts), encoding="utf-8")
     print(f"Written {index_path}")
 
+    # Fail loudly if doc/myst.yml's api/ TOC entries no longer match what we
+    # generated. Without this check, mismatches only manifest as easy-to-miss
+    # warnings in the jupyter-book log (--strict does not treat them as errors)
+    # and silently break the Read the Docs build downstream.
+    print("Validating doc/myst.yml stays in sync with generated API pages...")
+    rc = validate_docs.main()
+    if rc != 0:
+        sys.exit(rc)
+
 
 if __name__ == "__main__":
     main()

build_scripts/validate_docs.py

@@ -33,14 +33,21 @@ def parse_toc_files(toc_entries: list, files: set | None = None) -> set[str]:
 
 
 def validate_toc_files(toc_files: set[str], doc_root: Path) -> list[str]:
-    """Check that all files referenced in the TOC exist."""
-    # Directories with auto-generated content (gitignored, created during build)
-    generated_dirs = {"api/", "api\\"}
+    """Check that all files referenced in the TOC exist.
+
+    Auto-generated ``api/*.md`` pages are produced by
+    ``build_scripts/gen_api_md.py`` and are gitignored, so they are skipped
+    while the ``doc/api/`` directory has not been generated yet (e.g. during
+    pre-commit). Once that directory exists (i.e. after a docs build), the
+    api/ entries are validated like any other file so the TOC stays in sync
+    with the generator output.
+    """
+    skip_generated_api = not (doc_root / "api").exists()
+    api_prefixes = ("api/", "api\\")
 
     errors = []
     for file_ref in toc_files:
-        # Skip files in auto-generated directories
-        if any(file_ref.startswith(d) for d in generated_dirs):
+        if skip_generated_api and file_ref.startswith(api_prefixes):
             continue
         file_path = doc_root / file_ref
         if not file_path.exists():
@@ -49,17 +56,24 @@ def validate_toc_files(toc_files: set[str], doc_root: Path) -> list[str]:
 
 
 def find_orphaned_files(toc_files: set[str], doc_root: Path) -> list[str]:
-    """Find documentation files not referenced in the TOC."""
+    """Find documentation files not referenced in the TOC.
+
+    ``doc/api/`` holds auto-generated reference pages. They are skipped while
+    the directory does not yet exist (pre-commit, before any docs build), but
+    once present they are checked for orphans so the TOC reflects exactly the
+    set of files produced by ``build_scripts/gen_api_md.py``.
+    """
     skip_dirs = {
         "_build",
         "_api",
-        "api",
         "css",
         ".ipynb_checkpoints",
         "__pycache__",
         "playwright_demo",
         "generate_docs",
     }
+    if not (doc_root / "api").exists():
+        skip_dirs.add("api")
     skip_files = {
         "myst.yml",
         "roakey.png",

doc/myst.yml

@@ -208,7 +208,6 @@ project:
         - file: api/pyrit_cli_pyrit_scan.md
         - file: api/pyrit_cli_pyrit_shell.md
         - file: api/pyrit_common.md
-        - file: api/pyrit_common_cli_helpers.md
         - file: api/pyrit_datasets.md
         - file: api/pyrit_embedding.md
         - file: api/pyrit_exceptions.md
@@ -221,6 +220,7 @@ project:
         - file: api/pyrit_memory.md
         - file: api/pyrit_message_normalizer.md
         - file: api/pyrit_models.md
+        - file: api/pyrit_output.md
         - file: api/pyrit_prompt_converter.md
         - file: api/pyrit_prompt_normalizer.md
         - file: api/pyrit_prompt_target.md

tests/unit/build_scripts/test_validate_docs.py

@@ -49,10 +49,25 @@ def test_validate_toc_files_error_when_file_missing(tmp_path: Path) -> None:
 
 
 def test_validate_toc_files_skips_api_generated_files(tmp_path: Path) -> None:
+    # When doc/api/ does not exist (e.g. pre-commit before any docs build),
+    # api/* TOC entries are skipped because they will be generated later.
     errors = validate_toc_files({"api/some_module"}, tmp_path)
     assert errors == []
 
 
+def test_validate_toc_files_validates_api_entries_when_api_dir_exists(tmp_path: Path) -> None:
+    # Once doc/api/ exists (post gen_api_md.py), api/* TOC entries are
+    # validated like any other file so stale entries are caught.
+    api_dir = tmp_path / "api"
+    api_dir.mkdir()
+    (api_dir / "pyrit_existing.md").write_text("# existing")
+
+    errors = validate_toc_files({"api/pyrit_existing.md", "api/pyrit_missing.md"}, tmp_path)
+
+    assert len(errors) == 1
+    assert "pyrit_missing.md" in errors[0]
+
+
 def test_validate_toc_files_multiple_missing_files(tmp_path: Path) -> None:
     errors = validate_toc_files({"a.md", "b.md"}, tmp_path)
     assert len(errors) == 2
@@ -89,3 +104,18 @@ def test_find_orphaned_files_skips_py_companion_files(tmp_path: Path) -> None:
     (tmp_path / "notebook.py").write_text("# companion")
     orphaned = find_orphaned_files(set(), tmp_path)
     assert not any("notebook.py" in o for o in orphaned)
+
+
+def test_find_orphaned_files_detects_orphaned_api_pages_when_dir_exists(tmp_path: Path) -> None:
+    # Post-build: doc/api/ exists. Any generated page that isn't in the TOC
+    # is flagged so stale or unlisted modules surface immediately instead of
+    # showing up later as a Read the Docs build failure.
+    api_dir = tmp_path / "api"
+    api_dir.mkdir()
+    (api_dir / "pyrit_listed.md").write_text("# listed")
+    (api_dir / "pyrit_orphan.md").write_text("# orphan")
+
+    orphaned = find_orphaned_files({"api/pyrit_listed.md"}, tmp_path)
+
+    assert any("pyrit_orphan.md" in o for o in orphaned)
+    assert not any("pyrit_listed.md" in o for o in orphaned)