diff --git a/scripts/powershell/common.ps1 b/scripts/powershell/common.ps1
index f56fc26577..5161fce1ad 100644
--- a/scripts/powershell/common.ps1
+++ b/scripts/powershell/common.ps1
@@ -209,7 +209,13 @@ function Test-FileExists {
 
 function Test-DirHasFiles {
     param([string]$Path, [string]$Description)
-    if ((Test-Path -Path $Path -PathType Container) -and (Get-ChildItem -Path $Path -ErrorAction SilentlyContinue | Where-Object { -not $_.PSIsContainer } | Select-Object -First 1)) {
+    # A directory counts as non-empty when Get-ChildItem returns any entry
+    # (files or subdirectories) — matching the JSON contracts checks in
+    # check-prerequisites.ps1 / setup-tasks.ps1, and treating a directory whose
+    # only contents are subdirectories (e.g. contracts/v1/openapi.yaml) as
+    # non-empty like bash check_dir. Filtering out subdirectories would
+    # mis-report such a directory as empty.
+    if ((Test-Path -Path $Path -PathType Container) -and (Get-ChildItem -Path $Path -ErrorAction SilentlyContinue | Select-Object -First 1)) {
         Write-Output "  [OK] $Description"
         return $true
     } else {
diff --git a/tests/test_setup_tasks.py b/tests/test_setup_tasks.py
index 0e3fb85f41..25faa1ed22 100644
--- a/tests/test_setup_tasks.py
+++ b/tests/test_setup_tasks.py
@@ -840,3 +840,49 @@ def test_setup_tasks_ps_errors_without_feature_context(
     output = result.stderr + result.stdout
     assert result.returncode != 0
     assert "Feature directory not found" in output
+
+
+# ---------------------------------------------------------------------------
+# Directory non-emptiness parity: a dir whose only contents are subdirectories
+# (e.g. contracts/v1/openapi.yaml) must count as non-empty in both shells.
+# ---------------------------------------------------------------------------
+
+def _run_bash_check_dir(repo: Path, target: Path) -> subprocess.CompletedProcess:
+    script = repo / ".specify" / "scripts" / "bash" / "common.sh"
+    return subprocess.run(
+        ["bash", "-c", 'source "$1"; check_dir "$2" "contracts/"', "bash", str(script), str(target)],
+        cwd=repo, capture_output=True, text=True, check=False, env=_clean_env(),
+    )
+
+
+def _run_powershell_test_dir(repo: Path, target: Path) -> subprocess.CompletedProcess:
+    script = repo / ".specify" / "scripts" / "powershell" / "common.ps1"
+    exe = "pwsh" if HAS_PWSH else _WINDOWS_POWERSHELL
+    return subprocess.run(
+        [exe, "-NoProfile", "-Command",
+         '& { param($common, $dir) . $common; Test-DirHasFiles -Path $dir -Description "contracts/" }',
+         str(script), str(target)],
+        cwd=repo, capture_output=True, text=True, check=False, env=_clean_env(),
+    )
+
+
+@requires_bash
+def test_check_dir_bash_counts_subdir_only_contracts(tasks_repo: Path) -> None:
+    """bash check_dir treats a dir containing only subdirectories as non-empty."""
+    contracts = tasks_repo / "contracts" / "v1"
+    contracts.mkdir(parents=True)
+    (contracts / "openapi.yaml").write_text("openapi: 3.0\n", encoding="utf-8")
+    result = _run_bash_check_dir(tasks_repo, tasks_repo / "contracts")
+    assert result.returncode == 0, result.stderr
+    assert "✓" in result.stdout and "✗" not in result.stdout
+
+
+@pytest.mark.skipif(not (HAS_PWSH or _WINDOWS_POWERSHELL), reason="no PowerShell available")
+def test_dir_has_files_ps_counts_subdir_only_contracts(tasks_repo: Path) -> None:
+    """Test-DirHasFiles must match bash: a subdir-only dir counts as non-empty."""
+    contracts = tasks_repo / "contracts" / "v1"
+    contracts.mkdir(parents=True)
+    (contracts / "openapi.yaml").write_text("openapi: 3.0\n", encoding="utf-8")
+    result = _run_powershell_test_dir(tasks_repo, tasks_repo / "contracts")
+    assert result.returncode == 0, result.stderr
+    assert "[OK]" in result.stdout and "[FAIL]" not in result.stdout