diff --git a/.github/workflows/native-service.yml b/.github/workflows/native-service.yml
index bf4875750..a9952ab06 100644
--- a/.github/workflows/native-service.yml
+++ b/.github/workflows/native-service.yml
@@ -116,6 +116,13 @@ jobs:
           uv venv .native-venv
           uv pip install --python .native-venv\Scripts\python.exe "powercontext[cli,server] @ $wheelUri" pytest
 
+      - name: Verify binary cursor persistence and restart compatibility
+        shell: pwsh
+        run: >-
+          .native-venv\Scripts\python.exe -m pytest -q
+          tests/test_cursor_secret.py
+          tests/test_server.py::test_server_reuses_file_backed_cursor_secret_across_restarts
+
       - name: Exercise the real Task Scheduler lifecycle
         shell: pwsh
         run: >-
@@ -127,6 +134,13 @@ jobs:
         if: failure()
         shell: pwsh
         run: |
+          Get-ChildItem -LiteralPath "$env:RUNNER_TEMP\powercontext-native-tests" -Recurse -File -ErrorAction SilentlyContinue |
+            Where-Object { $_.Name -in @('server.stdout.log', 'server.stderr.log') } |
+            ForEach-Object {
+              Write-Output "::group::$($_.FullName)"
+              Get-Content -LiteralPath $_.FullName -Tail 100
+              Write-Output "::endgroup::"
+            }
           schtasks.exe /Query /TN "$env:POWERCONTEXT_NATIVE_SERVICE_IDENTIFIER" /XML /HRESULT
           if ($LASTEXITCODE -ne 0) { exit 0 }
           schtasks.exe /Query /TN "$env:POWERCONTEXT_NATIVE_SERVICE_IDENTIFIER" /FO LIST /V /HRESULT
diff --git a/src/powercontext/server/cursor_secret.py b/src/powercontext/server/cursor_secret.py
index 66310ae28..be8815fff 100644
--- a/src/powercontext/server/cursor_secret.py
+++ b/src/powercontext/server/cursor_secret.py
@@ -53,7 +53,9 @@ def _load_or_create(path: Path) -> bytes:
 
     generated = secrets.token_bytes(_CURSOR_SECRET_BYTES)
     try:
-        descriptor = os.open(path, os.O_WRONLY | os.O_CREAT | os.O_EXCL, 0o600)
+        # Windows text descriptors translate LF bytes even when using os.write.
+        flags = os.O_WRONLY | os.O_CREAT | os.O_EXCL | getattr(os, "O_BINARY", 0)
+        descriptor = os.open(path, flags, 0o600)
     except FileExistsError:
         return _read(path)
     try:
diff --git a/tests/test_cursor_secret.py b/tests/test_cursor_secret.py
index 613813b37..74988d447 100644
--- a/tests/test_cursor_secret.py
+++ b/tests/test_cursor_secret.py
@@ -14,8 +14,10 @@
 
 from __future__ import annotations
 
+import os
 import stat
 
+import pytest
 from pydantic import SecretStr
 
 from powercontext.builtin.persistence.oceanbase import OceanBaseConfig
@@ -23,7 +25,16 @@
 from powercontext.server.cursor_secret import resolve_cursor_secret
 
 
-def test_file_backed_sqlite_reuses_private_cursor_secret(tmp_path) -> None:
+@pytest.fixture
+def generated_secret(monkeypatch) -> bytes:
+    # Include LF and other control bytes so Windows text translation cannot hide
+    # behind a randomly generated key that happens not to contain a newline.
+    secret = bytes(range(32))
+    monkeypatch.setattr("powercontext.server.cursor_secret.secrets.token_bytes", lambda size: secret[:size])
+    return secret
+
+
+def test_file_backed_sqlite_reuses_private_cursor_secret(tmp_path, generated_secret) -> None:
     database_path = tmp_path / "powercontext.db"
     config = SQLiteConfig(url=f"sqlite+aiosqlite:///{database_path}")
 
@@ -31,9 +42,10 @@ def test_file_backed_sqlite_reuses_private_cursor_secret(tmp_path) -> None:
     second = resolve_cursor_secret(config, None)
 
     key_path = tmp_path / ".powercontext.db.cursor-key"
-    assert first == second
-    assert first is not None and len(first) == 32
-    assert stat.S_IMODE(key_path.stat().st_mode) == 0o600
+    assert first == second == generated_secret
+    assert key_path.read_bytes() == generated_secret
+    if os.name != "nt":
+        assert stat.S_IMODE(key_path.stat().st_mode) == 0o600
 
 
 def test_explicit_cursor_secret_overrides_database_storage(tmp_path) -> None:
@@ -46,13 +58,17 @@ def test_explicit_cursor_secret_overrides_database_storage(tmp_path) -> None:
     assert not (tmp_path / ".powercontext.db.cursor-key").exists()
 
 
-def test_remote_database_without_override_reuses_local_persisted_secret(tmp_path, monkeypatch) -> None:
+def test_remote_database_without_override_reuses_local_persisted_secret(
+    tmp_path, monkeypatch, generated_secret
+) -> None:
     monkeypatch.setenv("POWERCONTEXT_HOME", str(tmp_path))
     config = OceanBaseConfig(url=SecretStr("mysql+aoceanbase://user:password@127.0.0.1:2881/test?charset=utf8mb4"))
 
     first = resolve_cursor_secret(config, None)
     second = resolve_cursor_secret(config, None)
 
-    assert first == second
-    assert first is not None and len(first) == 32
-    assert stat.S_IMODE((tmp_path / "cursor-signing.key").stat().st_mode) == 0o600
+    key_path = tmp_path / "cursor-signing.key"
+    assert first == second == generated_secret
+    assert key_path.read_bytes() == generated_secret
+    if os.name != "nt":
+        assert stat.S_IMODE(key_path.stat().st_mode) == 0o600
diff --git a/tests/test_server.py b/tests/test_server.py
index 88bfc84b4..75916df8e 100644
--- a/tests/test_server.py
+++ b/tests/test_server.py
@@ -180,7 +180,8 @@ def test_server_settings_configure_default_project_skill_targets(tmp_path, monke
     assert all(target.allow_managed_publish for target in settings.external_skills.targets)
 
 
-def test_server_reuses_file_backed_cursor_secret_across_restarts(tmp_path) -> None:
+def test_server_reuses_file_backed_cursor_secret_across_restarts(tmp_path, monkeypatch) -> None:
+    monkeypatch.setattr("powercontext.server.cursor_secret.secrets.token_bytes", lambda size: b"\n" * size)
     database = SQLiteConfig(url=f"sqlite+aiosqlite:///{tmp_path / 'runtime.db'}")
     settings = ServerSettings(
         database=database,