diff --git a/scripts/python/setup_tasks.py b/scripts/python/setup_tasks.py
index b3abb6dc1a..21b0018620 100644
--- a/scripts/python/setup_tasks.py
+++ b/scripts/python/setup_tasks.py
@@ -55,14 +55,31 @@ def _available_docs(paths: FeaturePaths) -> list[str]:
     return docs
 
 
+def _status_marker(ok: bool) -> str:
+    """Return the status glyph, downgraded to ASCII when stdout cannot encode it.
+
+    On Windows sys.stdout falls back to the ANSI code page whenever it is not a
+    console - a pipe or a file redirect, which is how agents and workflow steps
+    invoke these scripts - and U+2713 is unencodable in cp1252, so printing it
+    raised UnicodeEncodeError and aborted the report mid-listing.
+    "[OK]"/"[FAIL]" is the ASCII rendering these markers already have in-tree:
+    see Test-FileExists in scripts/powershell/common.ps1 and
+    normalize_status_text in tests/parity_helpers.py.
+    """
+    glyph = "✓" if ok else "✗"
+    try:
+        glyph.encode(getattr(sys.stdout, "encoding", None) or "utf-8")
+    except (LookupError, UnicodeEncodeError):
+        return "[OK]" if ok else "[FAIL]"
+    return glyph
+
+
 def _check_file(path: Path, description: str) -> None:
-    marker = "✓" if path.is_file() else "✗"
-    print(f"  {marker} {description}")
+    print(f"  {_status_marker(path.is_file())} {description}")
 
 
 def _check_dir(path: Path, description: str) -> None:
-    marker = "✓" if _dir_has_entries(path) else "✗"
-    print(f"  {marker} {description}")
+    print(f"  {_status_marker(_dir_has_entries(path))} {description}")
 
 
 def main(argv: list[str] | None = None) -> int:
diff --git a/tests/test_setup_tasks_python_parity.py b/tests/test_setup_tasks_python_parity.py
index 29d0e2b5aa..afa303b6bd 100644
--- a/tests/test_setup_tasks_python_parity.py
+++ b/tests/test_setup_tasks_python_parity.py
@@ -205,3 +205,28 @@ def test_missing_template_error_matches_all_variants(repo: Path) -> None:
     assert bash.returncode == ps.returncode == py.returncode == 1
     assert bash.stdout == ps.stdout == py.stdout == ""
     assert bash.stderr == ps.stderr == py.stderr
+
+
+def test_python_text_output_survives_a_legacy_stdout_code_page(repo: Path) -> None:
+    """Text mode must not crash when stdout cannot encode the status glyphs.
+
+    On Windows sys.stdout falls back to the ANSI code page whenever it is not a
+    console — which is every time an agent or a workflow step captures the
+    output. U+2713 is unencodable in cp1252, so printing it raised
+    UnicodeEncodeError and truncated the document listing. The ASCII fallback is
+    the rendering these markers already have in-tree (Test-FileExists in
+    scripts/powershell/common.ps1, and normalize_status_text).
+    """
+    feature = repo / "specs" / "001-my-feature"
+    (feature / "research.md").write_text("# research\n", encoding="utf-8")
+    (feature / "contracts").mkdir()
+
+    env = clean_env()
+    env["PYTHONIOENCODING"] = "cp1252"
+    result = run(py_cmd(repo, SCRIPT), repo, env=env)
+
+    assert result.returncode == 0, result.stderr
+    assert "UnicodeEncodeError" not in result.stderr
+    for doc in ("research.md", "data-model.md", "contracts/", "quickstart.md"):
+        assert doc in result.stdout, (doc, result.stdout)
+    assert "[OK] research.md" in normalize_status_text(result.stdout), result.stdout