diff --git a/tests/test_cli/test_grants_cmd.py b/tests/test_cli/test_grants_cmd.py
index fe7d9a6..e13892c 100644
--- a/tests/test_cli/test_grants_cmd.py
+++ b/tests/test_cli/test_grants_cmd.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import json
 from typing import TYPE_CHECKING
 
 import pytest
@@ -147,7 +148,10 @@ async def test_config_allow_paths_installed(
 ) -> None:
     outside = (tmp_path.parent / "outside-config").resolve()
     outside.mkdir(exist_ok=True)
-    document = tomlkit.parse(f'[agent]\nallow_paths = {{ "{outside}" = "read", "/does/not/exist" = "read" }}\n')
+    # JSON string escaping is TOML escaping too, so a Windows path's backslashes
+    # survive instead of reading as an escape (``\u``).
+    key = json.dumps(str(outside))
+    document = tomlkit.parse(f'[agent]\nallow_paths = {{ {key} = "read", "/does/not/exist" = "read" }}\n')
     state, memory = await _new_state(tmp_path, document=document)
     try:
         assert state.instance_state.workspace.config_allow == {outside: AccessMode.READ}
diff --git a/tests/test_cli/test_interrupt.py b/tests/test_cli/test_interrupt.py
index d09e4e6..267bda6 100644
--- a/tests/test_cli/test_interrupt.py
+++ b/tests/test_cli/test_interrupt.py
@@ -3,6 +3,7 @@ from __future__ import annotations
 import asyncio
 import os
 import signal
+import sys
 import threading
 import time
 from typing import TYPE_CHECKING
@@ -35,6 +36,14 @@ if TYPE_CHECKING:
 
     import pytest as pytest_module
 
+# The router is asyncio's SIGINT handler, which only exists where signals do; on
+# Windows a test could not deliver one either — ``os.kill(pid, SIGINT)`` is
+# ``TerminateProcess`` there, so it kills the runner instead of interrupting it.
+pytestmark = pytest.mark.skipif(
+    sys.platform == "win32",
+    reason="SIGINT routing needs POSIX signal handling",
+)
+
 
 class FakeTarget:
     """Minimal ``InterruptTarget`` recording its cancels."""
diff --git a/tests/test_cli/test_skills_cmd.py b/tests/test_cli/test_skills_cmd.py
index d7ac964..6e5becd 100644
--- a/tests/test_cli/test_skills_cmd.py
+++ b/tests/test_cli/test_skills_cmd.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import json
 from typing import TYPE_CHECKING
 
 import pytest
@@ -44,7 +45,9 @@ def _skill_notice_rows(state: ReplState) -> list[str]:
 def _config_doc(tmp_path: Path, *, paths: list[Path] | None = None, extra: str = "") -> tomlkit.TOMLDocument:
     lines = ["[skills]", "discover = []"]
     if paths:
-        rendered = ", ".join(f'"{path}"' for path in paths)
+        # JSON string escaping is TOML escaping too, so a Windows path's
+        # backslashes survive instead of reading as an escape (``\u``).
+        rendered = ", ".join(json.dumps(str(path)) for path in paths)
         lines.append(f"paths = [{rendered}]")
     if extra:
         lines.append(extra)
@@ -215,12 +218,12 @@ async def test_skill_tools_are_offered_and_can_read_skill_files(
 
     skill_file = skills_state.skills.skills[0].skill_file if skills_state.skills else None
     assert skill_file is not None
-    read = await skills_state.agent.tools.execute("read_file", f'{{"path": "{skill_file}"}}')
+    read = await skills_state.agent.tools.execute("read_file", json.dumps({"path": str(skill_file)}))
     assert "Deploy the acme stack" in read
 
     denied = await skills_state.agent.tools.execute(
         "write_file",
-        f'{{"path": "{skill_file}", "content": "x"}}',
+        json.dumps({"path": str(skill_file), "content": "x"}),
     )
     assert denied.startswith("error:")
     assert "escapes workspace root" in denied
diff --git a/tests/test_skills/test_discovery.py b/tests/test_skills/test_discovery.py
index 61e1013..6ca3061 100644
--- a/tests/test_skills/test_discovery.py
+++ b/tests/test_skills/test_discovery.py
@@ -1,13 +1,10 @@
 from __future__ import annotations
 
-from typing import TYPE_CHECKING
+from pathlib import Path
 
 from plyngent.config.models import SkillsConfig
 from plyngent.skills import SKILL_FILE, Skill, SkillStore, build_roots, validate_skill_name
 
-if TYPE_CHECKING:
-    from pathlib import Path
-
 
 def _write_skill(root: Path, name: str, *, description: str | None = "A test skill", body: str = "Body.") -> Path:
     directory = root / name
@@ -28,12 +25,13 @@ def test_build_roots_orders_explicit_paths_first(tmp_path: Path) -> None:
         user_config_dir=tmp_path / "config",
         home=tmp_path / "home",
     )
-    assert [(r.origin, r.scope, str(r.path)) for r in roots] == [
-        ("config", "user", str(tmp_path / "home" / "team-skills")),
-        ("config", "user", "/srv/skills"),
-        ("plyngent", "user", str(tmp_path / "config" / "skills")),
-        ("claude", "user", str(tmp_path / "home" / ".claude" / "skills")),
-        ("claude", "project", str(tmp_path / "proj" / ".claude" / "skills")),
+    # Paths, not strings: a Windows run spells the same root differently.
+    assert [(r.origin, r.scope, r.path) for r in roots] == [
+        ("config", "user", tmp_path / "home" / "team-skills"),
+        ("config", "user", Path("/srv/skills")),
+        ("plyngent", "user", tmp_path / "config" / "skills"),
+        ("claude", "user", tmp_path / "home" / ".claude" / "skills"),
+        ("claude", "project", tmp_path / "proj" / ".claude" / "skills"),
     ]