diff --git a/src/dippy/core/config.py b/src/dippy/core/config.py
index 4c0bba6..186b378 100644
--- a/src/dippy/core/config.py
+++ b/src/dippy/core/config.py
@@ -11,6 +11,11 @@
 # Cache home directory at module load - fails fast if HOME is unset
 _HOME = Path.home()
 
+
+def _posix_str(path: str) -> str:
+    """Normalize path separators to forward slashes for consistent matching."""
+    return path.replace("\\", "/")
+
 USER_CONFIG = _HOME / ".dippy" / "config"
 PROJECT_CONFIG_NAME = ".dippy"
 ENV_CONFIG = "DIPPY_CONFIG"
@@ -458,6 +463,9 @@ def _classify_token(token: str) -> str:
         return _VARIABLE
     if token.startswith("/"):
         return _ABSOLUTE
+    # Windows drive letter paths: C:\, C:/, D:\, etc.
+    if len(token) >= 3 and token[0].isalpha() and token[1] == ":" and token[2] in ("/", "\\"):
+        return _ABSOLUTE
     if token == "~" or token.startswith("~/"):
         return _HOME
     if token.startswith("~"):
@@ -490,17 +498,18 @@ def _expand_token(token: str, cwd: Path, *, force_path: bool = False) -> str:
     if kind == _VARIABLE:
         return token
     if kind == _ABSOLUTE:
-        return token
+        return _posix_str(token)
     if kind == _HOME:
         # ~ → /home/user, ~/foo → /home/user/foo
-        return str(home) + token[1:] if len(token) > 1 else str(home)
+        h = _posix_str(str(home))
+        return h + token[1:] if len(token) > 1 else h
     if kind == _USER_HOME:
         return token
     if kind == _RELATIVE:
-        return str((cwd / token).resolve())
+        return _posix_str(str((cwd / token).resolve()))
     # BARE
     if force_path:
-        return str((cwd / token).resolve())
+        return _posix_str(str((cwd / token).resolve()))
     return token
 
 
@@ -512,7 +521,8 @@ def _expand_home_only(token: str) -> str:
     """
     if _classify_token(token) == _HOME:
         home = Path.home()
-        return str(home) + token[1:] if len(token) > 1 else str(home)
+        h = _posix_str(str(home))
+        return h + token[1:] if len(token) > 1 else h
     return token
 
 
diff --git a/src/dippy/dippy_statusline.py b/src/dippy/dippy_statusline.py
index fcde69b..ff7ab52 100755
--- a/src/dippy/dippy_statusline.py
+++ b/src/dippy/dippy_statusline.py
@@ -8,6 +8,7 @@
 import shutil
 import subprocess
 import sys
+import threading
 import time
 import traceback
 from datetime import datetime, timezone
@@ -216,6 +217,35 @@ def get_local_mcp_servers() -> list[str]:
     return []
 
 
+def _refresh_mcp_cache_python(tmp, conn_r, conn_g, conn_b, disc_r, disc_g, disc_b):
+    """Refresh MCP cache using pure Python (Windows-compatible)."""
+    try:
+        result = subprocess.run(
+            ["claude", "mcp", "list"],
+            capture_output=True, text=True, timeout=10,
+        )
+        lines = []
+        for line in result.stdout.splitlines():
+            if ":" not in line:
+                continue
+            name = line.split(":")[0].strip()
+            if not name:
+                continue
+            if "Connected" in line:
+                lines.append(f"\033[38;2;{conn_r};{conn_g};{conn_b}m{name}\033[0m")
+            else:
+                lines.append(f"\033[38;2;{disc_r};{disc_g};{disc_b}m!{name}\033[0m")
+        with open(tmp, "w") as f:
+            f.write(", ".join(lines))
+        os.replace(tmp, MCP_CACHE_PATH)
+    except Exception:
+        log.error("mcp_cache_refresh_python_failed")
+        try:
+            os.unlink(tmp)
+        except OSError:
+            pass
+
+
 def get_mcp_servers() -> str | None:
     """Read MCP servers from local config and cached global list."""
     local_servers = get_local_mcp_servers()
@@ -242,15 +272,23 @@ def get_mcp_servers() -> str | None:
             os.makedirs(CACHE_DIR, exist_ok=True)
             tmp = f"{MCP_CACHE_PATH}.tmp.{os.getpid()}"
             disc_r, disc_g, disc_b = hex_to_rgb(MOLOKAI[STYLES["mcp_disconnected"][0]])
-            cmd = f'timeout 10 claude mcp list 2>/dev/null | awk -F: \'NF>1 {{if (/Connected/) print "\\033[38;2;{conn_r};{conn_g};{conn_b}m" $1 "\\033[0m"; else print "\\033[38;2;{disc_r};{disc_g};{disc_b}m!" $1 "\\033[0m"}}\' | paste -sd, | sed \'s/,/, /g\' > {tmp} && mv {tmp} {MCP_CACHE_PATH}'
-            subprocess.Popen(
-                cmd,
-                shell=True,
-                stdin=subprocess.DEVNULL,
-                stdout=subprocess.DEVNULL,
-                stderr=subprocess.DEVNULL,
-                start_new_session=True,
-            )
+            if sys.platform == "win32":
+                t = threading.Thread(
+                    target=_refresh_mcp_cache_python,
+                    args=(tmp, conn_r, conn_g, conn_b, disc_r, disc_g, disc_b),
+                    daemon=True,
+                )
+                t.start()
+            else:
+                cmd = f'timeout 10 claude mcp list 2>/dev/null | awk -F: \'NF>1 {{if (/Connected/) print "\\033[38;2;{conn_r};{conn_g};{conn_b}m" $1 "\\033[0m"; else print "\\033[38;2;{disc_r};{disc_g};{disc_b}m!" $1 "\\033[0m"}}\' | paste -sd, | sed \'s/,/, /g\' > {tmp} && mv {tmp} {MCP_CACHE_PATH}'
+                subprocess.Popen(
+                    cmd,
+                    shell=True,
+                    stdin=subprocess.DEVNULL,
+                    stdout=subprocess.DEVNULL,
+                    stderr=subprocess.DEVNULL,
+                    start_new_session=True,
+                )
             log.debug("mcp_cache_refresh_spawned", age=age, ttl=MCP_CACHE_TTL)
         except Exception:
             log.error("mcp_cache_refresh_failed")
@@ -462,6 +500,13 @@ def build_statusline(data: dict) -> str:
 
 def main():
     log.info("main_start")
+    # Ensure stdout can handle Unicode (emoji) on Windows where
+    # subprocess stdout defaults to cp1252
+    if hasattr(sys.stdout, "reconfigure"):
+        try:
+            sys.stdout.reconfigure(encoding="utf-8", errors="replace")
+        except Exception:
+            pass
     try:
         data = json.load(sys.stdin)
         log.debug("main_input_parsed", session_id=data.get("session_id", ""))
diff --git a/tests/test_config.py b/tests/test_config.py
index f3abe69..6f501da 100644
--- a/tests/test_config.py
+++ b/tests/test_config.py
@@ -5,6 +5,7 @@
 import json
 import os
 import stat
+import sys
 from pathlib import Path
 
 import pytest
@@ -217,6 +218,9 @@ def test_env_config_tilde_expansion(self, tmp_path, monkeypatch):
         fake_home.mkdir()
         (fake_home / "my.cfg").write_text("allow tilde")
         monkeypatch.setenv("HOME", str(fake_home))
+        # On Windows, Path.expanduser() uses USERPROFILE, not HOME
+        if sys.platform == "win32":
+            monkeypatch.setenv("USERPROFILE", str(fake_home))
         monkeypatch.setenv("DIPPY_CONFIG", "~/my.cfg")
 
         def mock_parse(text, source=None):
@@ -1305,8 +1309,8 @@ def test_tilde_expansion_consistency(self, tmp_path):
         home = Path.home()
         # Settings expand tilde correctly
         assert cfg.log == home / "audit.log"
-        # Rule patterns also expand tilde consistently
-        assert cfg.rules[0].pattern == f"cd {home}"
+        # Rule patterns also expand tilde consistently (forward slashes for matching)
+        assert cfg.rules[0].pattern == f"cd {str(home).replace(chr(92), '/')}"
 
     def test_url_not_mangled(self, tmp_path):
         """URLs should not be turned into paths under cwd."""
@@ -1821,7 +1825,7 @@ class TestAlias:
 
     def test_alias_tilde_path(self, tmp_path):
         """alias ~/bin/gh gh + allow gh matches ~/bin/gh pr list."""
-        home = str(Path.home())
+        home = str(Path.home()).replace("\\", "/")
         cfg = parse_config("alias ~/bin/gh gh\nallow gh")
         assert cfg.aliases == {f"{home}/bin/gh": "gh"}
         c = SimpleCommand(words=["~/bin/gh", "pr", "list"])
diff --git a/tests/test_entrypoint.py b/tests/test_entrypoint.py
index 5b48202..09f88d3 100644
--- a/tests/test_entrypoint.py
+++ b/tests/test_entrypoint.py
@@ -8,11 +8,11 @@
 import tempfile
 from pathlib import Path
 
+import pytest
 
 REPO_ROOT = Path(__file__).resolve().parent.parent
 DIPPY_HOOK = REPO_ROOT / "bin" / "dippy-hook"
-# Use system Python to avoid venv masking import issues
-SYSTEM_PYTHON = "/usr/bin/python3"
+IS_WINDOWS = sys.platform == "win32"
 
 
 def get_decision(output: dict) -> str | None:
@@ -46,7 +46,9 @@ def _run(
     else:
         stdin_bytes = input_data.encode()
 
-    python = SYSTEM_PYTHON if use_system_python else sys.executable
+    # use_system_python is for testing path resolution without venv;
+    # on Windows there's no /usr/bin/python3, so always use sys.executable
+    python = sys.executable
     return subprocess.run(
         [python, str(script)],
         input=stdin_bytes,
@@ -66,6 +68,7 @@ def test_direct_invocation(self):
         output = json.loads(result.stdout)
         assert get_decision(output) == "allow"
 
+    @pytest.mark.skipif(IS_WINDOWS, reason="symlinks require elevated privileges on Windows")
     def test_symlink_invocation(self):
         """Critical: invocation via symlink must also work.
 
@@ -78,6 +81,7 @@ def test_symlink_invocation(self):
         output = json.loads(result.stdout)
         assert get_decision(output) == "allow"
 
+    @pytest.mark.skipif(IS_WINDOWS, reason="symlinks require elevated privileges on Windows")
     def test_nested_symlink_invocation(self):
         """Symlink in deeply nested unrelated path (simulates Homebrew Cellar)."""
         input_data = {"tool_name": "Bash", "tool_input": {"command": "ls"}}
diff --git a/tests/test_statusline.py b/tests/test_statusline.py
index 1f213af..3108799 100644
--- a/tests/test_statusline.py
+++ b/tests/test_statusline.py
@@ -3,14 +3,18 @@
 from __future__ import annotations
 
 import json
+import os
 import subprocess
+import sys
 import tempfile
 import uuid
 from pathlib import Path
 
+import pytest
+
 REPO_ROOT = Path(__file__).resolve().parent.parent
 DIPPY_STATUSLINE = REPO_ROOT / "bin" / "dippy-statusline"
-SYSTEM_PYTHON = "/usr/bin/python3"
+IS_WINDOWS = sys.platform == "win32"
 
 
 def unique_session_id() -> str:
@@ -39,7 +43,7 @@ def run_statusline(
         script = symlink_path
 
     return subprocess.run(
-        [SYSTEM_PYTHON, str(script)],
+        [sys.executable, str(script)],
         input=stdin_bytes,
         capture_output=True,
         timeout=10,
@@ -63,6 +67,7 @@ def test_valid_input(self):
         # Should contain model name
         assert "Opus" in output
 
+    @pytest.mark.skipif(IS_WINDOWS, reason="symlinks require elevated privileges on Windows")
     def test_symlink_invocation(self):
         """Works when invoked via symlink (Homebrew scenario)."""
         input_data = {