diff --git a/scripts/check_conversion_retirements.py b/scripts/check_conversion_retirements.py
index 416e96aa2..9e4e07c9e 100644
--- a/scripts/check_conversion_retirements.py
+++ b/scripts/check_conversion_retirements.py
@@ -29,6 +29,38 @@ _TEST_ONLY_GROUPS = frozenset(
 )
 
 
+def _repository_paths_under(root: Path, relative: str) -> list[str] | None:
+    """Return repository-visible paths under ``relative``, or None if git cannot say.
+
+    Tracked files and untracked-but-unignored files both count. Ignored build
+    output does not: a checkout that removed a directory's sources leaves its
+    ``__pycache__`` behind, and that is a property of one operator's disk rather
+    than of the repository. Reporting it as an unfinished retirement sends the
+    reader to the wave author instead of to their own working tree.
+    """
+    try:
+        result = subprocess.run(
+            [
+                "git",
+                "ls-files",
+                "--cached",
+                "--others",
+                "--exclude-standard",
+                "--",
+                relative,
+            ],
+            cwd=root,
+            capture_output=True,
+            text=True,
+            check=False,
+        )
+    except OSError:
+        return None
+    if result.returncode != 0:
+        return None
+    return [line for line in result.stdout.splitlines() if line.strip()]
+
+
 class CheckResult(NamedTuple):
     ok: bool
     checked_waves: tuple[str, ...]
@@ -314,9 +346,20 @@ def check_repository(
 
         checked.append(wave_id)
         for python_root in python_roots:
-            if (root / python_root).exists():
+            survivors = _repository_paths_under(root, python_root)
+            if survivors is None:
+                # git could not answer; fall back to the on-disk test rather than
+                # reporting a retirement we cannot prove.
+                if (root / python_root).exists():
+                    violations.append(
+                        f"{wave_id}: declared Python root still exists: {python_root}"
+                    )
+                continue
+            if survivors:
                 violations.append(
-                    f"{wave_id}: declared Python root still exists: {python_root}"
+                    f"{wave_id}: declared Python root still exists: {python_root} "
+                    f"({len(survivors)} file(s) in the repository, e.g. "
+                    f"{survivors[0]})"
                 )
 
         normalized_distribution = _normalize_distribution(distribution)
diff --git a/tests/test_conversion_retirements.py b/tests/test_conversion_retirements.py
new file mode 100644
index 000000000..e3ed6078f
--- /dev/null
+++ b/tests/test_conversion_retirements.py
@@ -0,0 +1,99 @@
+# SPDX-License-Identifier: AGPL-3.0-only
+# Copyright (c) 2026 sol pbc
+
+"""The retirement check must describe the repository, not one operator's disk."""
+
+from __future__ import annotations
+
+import subprocess
+from pathlib import Path
+
+import scripts.check_conversion_retirements as checker
+
+MANIFEST = """\
+schema_version = 1
+dependency_files = ["pyproject.toml"]
+content_roots = ["src"]
+content_exclusions = []
+
+[[waves]]
+id = "sample-wave"
+status = "done"
+distribution = "retired-dist"
+python_roots = ["src/legacy"]
+import_roots = ["retired_dist"]
+test_only_dependency_locations = []
+"""
+
+
+def _git(repo: Path, *args: str) -> None:
+    subprocess.run(
+        ["git", "-c", "user.email=t@e", "-c", "user.name=t", *args],
+        cwd=repo,
+        check=True,
+    )
+
+
+def _repo(base: Path) -> Path:
+    base.mkdir(parents=True, exist_ok=True)
+    _git(base, "init", "-q")
+    (base / "pyproject.toml").write_text('[project]\nname = "x"\n', encoding="utf-8")
+    (base / ".gitignore").write_text("__pycache__/\n", encoding="utf-8")
+    (base / "src").mkdir()
+    (base / "src" / "keep.py").write_text("x = 1\n", encoding="utf-8")
+    _git(base, "add", "-A")
+    _git(base, "commit", "-qm", "base")
+    return base
+
+
+def _run(repo: Path, tmp_path: Path):
+    manifest = tmp_path / "conversion-retirements.toml"
+    manifest.write_text(MANIFEST, encoding="utf-8")
+    return checker.check_repository(repo, manifest)
+
+
+def test_retired_root_absent_passes(tmp_path):
+    repo = _repo(tmp_path / "r")
+
+    result = _run(repo, tmp_path)
+
+    assert result.ok, result.violations
+
+
+def test_retired_root_holding_only_ignored_build_output_passes(tmp_path):
+    """A checkout that removed the sources leaves __pycache__; the repo did not."""
+    repo = _repo(tmp_path / "r")
+    cache = repo / "src" / "legacy" / "__pycache__"
+    cache.mkdir(parents=True)
+    (cache / "mod.cpython-313.pyc").write_bytes(b"\x00")
+
+    result = _run(repo, tmp_path)
+
+    assert result.ok, result.violations
+
+
+def test_retired_root_with_tracked_source_still_fails(tmp_path):
+    repo = _repo(tmp_path / "r")
+    legacy = repo / "src" / "legacy"
+    legacy.mkdir(parents=True)
+    (legacy / "mod.py").write_text("x = 1\n", encoding="utf-8")
+    _git(repo, "add", "-A")
+    _git(repo, "commit", "-qm", "legacy")
+
+    result = _run(repo, tmp_path)
+
+    assert not result.ok
+    assert any("src/legacy" in item for item in result.violations), result.violations
+
+
+def test_retired_root_with_untracked_unignored_source_still_fails(tmp_path):
+    """Not a weakening: only ignored content is forgiven."""
+    repo = _repo(tmp_path / "r")
+    legacy = repo / "src" / "legacy"
+    legacy.mkdir(parents=True)
+    (legacy / "stray.py").write_text("x = 1\n", encoding="utf-8")
+
+    result = _run(repo, tmp_path)
+
+    assert not result.ok
+    assert any("src/legacy" in item for item in result.violations), result.violations