Fix Windows Server proxy: HKLM mirror, ProxySettingsPerUser fix, policy detect

On Server / GPO baselines, ProxySettingsPerUser=0 makes WinINet ignore HKCU entirely. When elevated, force the flag to 1 and mirror proxy values to HKLM root + Connections blob. Detect Group Policy proxy locks and surface them so the user knows browsers will keep the policy value. Add diagnose_system_proxy() logged on every chain engage.

Co-authored-by: Cursor <cursoragent@cursor.com>

proxy_chain_manager/app.py

@@ -24,6 +24,7 @@ from .config import (
     load_settings,
     merge_proxy_credentials,
     normalize_proxy_url,
+    parse_exit_proxy_input,
     redact_proxy_url,
     save_settings,
     split_proxy_for_edit,
@@ -490,7 +491,7 @@ def main() -> None:
     exit_test_dot.pack(side="left", padx=(8, 4))
     exit_proxy_entry = ctk.CTkEntry(
         exit_fix_frame,
-        placeholder_text="http://host:port  or  socks5://host:port  (optional)",
+        placeholder_text="host:port:user:pass   (defaults to socks5 — paste any format)",
         font=("Consolas", 10),
         fg_color=BG,
         border_color=ACCENT,
@@ -527,13 +528,49 @@ def main() -> None:
     exit_btn_row = ctk.CTkFrame(exit_fix_frame, fg_color="transparent")
     exit_btn_row.pack(fill="x", padx=10, pady=(0, 4))
 
+    def _auto_split_exit_paste(_event: Any | None = None) -> None:
+        """If the URL field looks like ``host:port:user:pass``, distribute
+        the user/pass parts into their own fields so the user sees what got
+        parsed. Triggered on key release and explicit paste.
+        """
+        raw = exit_proxy_entry.get()
+        if "://" in raw:
+            return
+        bits = [b for b in raw.strip().split(":") if b != ""]
+        if len(bits) < 4 and "@" not in raw and not any(c in raw for c in (" ", "\t")):
+            return
+        base, user, pw = parse_exit_proxy_input(raw, default_scheme="socks5")
+        if not base:
+            return
+        if base != raw:
+            exit_proxy_entry.delete(0, "end")
+            exit_proxy_entry.insert(0, base)
+        if user and not exit_user_entry.get().strip():
+            exit_user_entry.delete(0, "end")
+            exit_user_entry.insert(0, user)
+        if pw and not exit_pass_entry.get().strip():
+            exit_pass_entry.delete(0, "end")
+            exit_pass_entry.insert(0, pw)
+
+    exit_proxy_entry.bind("<KeyRelease>", _auto_split_exit_paste)
+    exit_proxy_entry.bind("<<Paste>>", lambda e: exit_proxy_entry.after(1, _auto_split_exit_paste))
+    exit_proxy_entry.bind("<FocusOut>", _auto_split_exit_paste)
+
     def _exit_url() -> str:
-        raw = exit_proxy_entry.get().strip()
+        """Build the final exit-proxy URL.
-        if not raw:
+
+        Accepts every paste format ``parse_exit_proxy_input`` understands
+        (host:port:user:pass, user:pass@host:port, scheme://…). Defaults to
+        SOCKS5 when no scheme is supplied.
+        """
+        base, parsed_user, parsed_pw = parse_exit_proxy_input(
+            exit_proxy_entry.get(), default_scheme="socks5"
+        )
+        if not base:
             return ""
-        if "://" not in raw:
+        user = (exit_user_entry.get() or "").strip() or parsed_user
-            raw = "http://" + raw
+        pw = (exit_pass_entry.get() or "").strip() or parsed_pw
-        return merge_proxy_credentials(raw, exit_user_entry.get(), exit_pass_entry.get())
+        return merge_proxy_credentials(base, user, pw)
 
     def _test_exit() -> None:
         url = _exit_url()
@@ -567,8 +604,11 @@ def main() -> None:
 
     ctk.CTkLabel(
         exit_fix_frame,
-        text="Appended after your chain hops when running. Leave empty to use last chain hop as exit.\n"
+        text=(
-             "Auth: User/Pass fields or user:pass@host in the URL.",
+            "Appended after your chain hops. Leave empty to use last chain hop as exit.\n"
+            "Paste any of:  host:port:user:pass  •  user:pass@host:port  •  scheme://host:port\n"
+            "No scheme = SOCKS5. Paste auto-splits into User/Pass below."
+        ),
         font=(FONT, 9),
         text_color=TEXT2,
         justify="left",
@@ -1247,11 +1287,7 @@ def main() -> None:
                 obfuscation_mode=mode_var.get(),
                 use_pinned_chain=bool(use_manual_var.get()),
                 pinned_chain=list(manual_chain),
-                manual_exit_proxy=merge_proxy_credentials(
+                manual_exit_proxy=_exit_url(),
-                    exit_proxy_entry.get(),
-                    exit_user_entry.get(),
-                    exit_pass_entry.get(),
-                ),
                 health_check_seconds=min(3600, max(10, int(entries["health"].get().strip()))),
                 full_refresh_seconds=min(86400, max(60, int(entries["refresh"].get().strip()))),
                 validation_concurrency=max(1, int(entries["conc"].get().strip())),

proxy_chain_manager/config.py

@@ -78,6 +78,57 @@ def merge_proxy_credentials(raw_url: str, username: str = "", password: str = ""
     return urlunparse((scheme, netloc, "", "", "", "")).rstrip("/")
 
 
+def parse_exit_proxy_input(
+    raw: str, default_scheme: str = "socks5"
+) -> tuple[str, str, str]:
+    """Parse any sane paste format into ``(base_url, user, password)``.
+
+    Accepts (whitespace-trimmed, default scheme = SOCKS5 when none given):
+
+      ``host:port``
+      ``host:port:user:password``
+      ``host:port:user:password:session_or_extra``  (extras folded into password)
+      ``host:port user password``                   (tab/space-separated)
+      ``user:password@host:port``
+      ``scheme://host:port``
+      ``scheme://user:password@host:port``
+
+    User and password may contain ``@``, ``:`` and arbitrary "words" — those
+    are URL-encoded automatically when ``merge_proxy_credentials`` rebuilds
+    the URL, so pasting plain text is safe.
+    """
+    t = (raw or "").strip()
+    if not t:
+        return "", "", ""
+
+    if "://" in t:
+        # Already a full URL — defer to the existing splitter.
+        return split_proxy_for_edit(t)
+
+    if "@" in t:
+        return split_proxy_for_edit(f"{default_scheme}://{t}")
+
+    if "\t" in t or any(c in t for c in (" ",)):
+        # "host:port user pass"  or  "host:port\tuser\tpass"
+        parts = [p for p in t.replace("\t", " ").split() if p]
+        if len(parts) >= 3:
+            hp, user, pw = parts[0], parts[1], " ".join(parts[2:])
+            return f"{default_scheme}://{hp}".rstrip("/"), user, pw
+        if len(parts) == 2:
+            return f"{default_scheme}://{parts[0]}".rstrip("/"), "", ""
+        t = parts[0]
+
+    bits = t.split(":")
+    if len(bits) >= 4:
+        host, port, user = bits[0], bits[1], bits[2]
+        password = ":".join(bits[3:])  # passwords containing ":" survive
+        return f"{default_scheme}://{host}:{port}", user, password
+    if len(bits) == 2:
+        return f"{default_scheme}://{bits[0]}:{bits[1]}", "", ""
+    # 1 token, or 3-token oddity — best-effort; treat as host[:port] only.
+    return f"{default_scheme}://{t}".rstrip("/"), "", ""
+
+
 def redact_proxy_url(url: str) -> str:
     """Same URL shape for logs/UI, with credentials replaced by ``***``."""
     t = (url or "").strip()

proxy_chain_manager/fingerprint.py

@@ -11,6 +11,7 @@ from dataclasses import dataclass, field
 
 from .firewall import is_admin
 from .mac_spoof import list_nics
+from .win_compat import probe as _win_probe
 
 log = logging.getLogger(__name__)
 
@@ -106,6 +107,11 @@ def disable_ipv6_on_adapters() -> tuple[list[str], list[str]]:
     """Disable IPv6 binding on up physical adapters. Returns (adapter names, log lines)."""
     if not is_admin():
         return [], ["IPv6 disable skipped (not Admin)."]
+    if not _win_probe().has_net_cmdlets:
+        return [], [
+            "IPv6 disable skipped — requires PowerShell 3.0+ "
+            "(Windows 8 / Server 2012+). Detected legacy PowerShell."
+        ]
     script = (
         "Get-NetAdapter | Where-Object { $_.Status -eq 'Up' } | "
         "ForEach-Object { $_.Name }"
@@ -135,6 +141,8 @@ def disable_ipv6_on_adapters() -> tuple[list[str], list[str]]:
 def enable_ipv6_on_adapters(adapters: list[str]) -> list[str]:
     if not is_admin() or not adapters:
         return []
+    if not _win_probe().has_net_cmdlets:
+        return []
     logs: list[str] = []
     for name in adapters:
         cmd = (

proxy_chain_manager/mac_spoof.py

@@ -8,6 +8,7 @@ import subprocess
 from dataclasses import dataclass
 
 from .firewall import is_admin
+from .win_compat import probe as _win_probe
 
 log = logging.getLogger(__name__)
 
@@ -36,7 +37,14 @@ def _run(args: list[str], timeout: float = 20.0) -> tuple[int, str, str]:
 
 
 def list_nics() -> list[NicMac]:
-    """Physical/up adapters with current MAC."""
+    """Physical/up adapters with current MAC.
+
+    Falls back to ``wmic nic`` for hosts without PowerShell 3.0 (Server 2008 R2).
+    """
+    compat = _win_probe()
+    if not compat.has_net_cmdlets:
+        return _list_nics_wmic()
+
     script = (
         "Get-NetAdapter | Where-Object { $_.Status -ne 'Disabled' } | "
         "Select-Object Name, MacAddress, InterfaceDescription | "
@@ -44,7 +52,7 @@ def list_nics() -> list[NicMac]:
     )
     code, out, _ = _run(["powershell", "-NoProfile", "-Command", script])
     if code != 0 or not out.strip():
-        return []
+        return _list_nics_wmic()
     import json
 
     try:
@@ -71,9 +79,46 @@ def random_mac() -> str:
     return ":".join(f"{x:02X}" for x in b)
 
 
+def _list_nics_wmic() -> list[NicMac]:
+    """Server 2008 R2 / PowerShell 2.0 fallback via wmic."""
+    code, out, _ = _run([
+        "wmic", "nic", "where", "NetEnabled=true",
+        "get", "NetConnectionID,MACAddress,Name", "/format:list",
+    ])
+    if code != 0 or not out:
+        return []
+    nics: list[NicMac] = []
+    cur = {"id": "", "mac": "", "name": ""}
+    for ln in out.splitlines():
+        s = ln.strip()
+        if not s:
+            if cur["id"] and cur["mac"]:
+                mac = cur["mac"].replace("-", ":")
+                if mac and mac != "00:00:00:00:00:00":
+                    nics.append(NicMac(name=cur["id"], mac=mac, description=cur["name"]))
+            cur = {"id": "", "mac": "", "name": ""}
+            continue
+        if s.startswith("NetConnectionID="):
+            cur["id"] = s.split("=", 1)[1].strip()
+        elif s.startswith("MACAddress="):
+            cur["mac"] = s.split("=", 1)[1].strip()
+        elif s.startswith("Name="):
+            cur["name"] = s.split("=", 1)[1].strip()
+    if cur["id"] and cur["mac"]:
+        mac = cur["mac"].replace("-", ":")
+        if mac and mac != "00:00:00:00:00:00":
+            nics.append(NicMac(name=cur["id"], mac=mac, description=cur["name"]))
+    return nics
+
+
 def set_mac(adapter: str, mac: str) -> tuple[bool, str]:
     if not is_admin():
         return False, "Administrator required to change MAC."
+    if not _win_probe().has_net_cmdlets:
+        return False, (
+            "MAC change requires PowerShell 3.0+ (Windows 8 / Server 2012+). "
+            "Detected legacy PowerShell — feature unavailable on this host."
+        )
     mac = mac.replace("-", ":").upper()
     if not _MAC_RE.match(mac.replace(":", "-")):
         return False, f"Invalid MAC: {mac}"

proxy_chain_manager/service.py

@@ -30,9 +30,16 @@ from .firewall import disengage as fw_disengage, engage as fw_engage, is_admin
 from .gost_util import build_gost_cmd, ensure_gost, popen_no_window, read_gost_log_tail, terminate_process
 from .leak_detect import is_chain_leak, leak_reason
 from .mac_spoof import restore_macs, spoof_all_physical
-from .sysproxy import clear_system_proxy, set_system_proxy
+from .sysproxy import (
+    clear_system_proxy,
+    detect_policy_overrides,
+    diagnose_system_proxy,
+    is_system_proxy_set,
+    set_system_proxy,
+)
 from .validator import check_chain_exit_ip, get_direct_ip, validate_proxies
 from .vpn_detect import VpnStatus, detect_vpn
+from .win_compat import probe as _win_probe
 
 log = logging.getLogger(__name__)
 
@@ -89,6 +96,17 @@ class ChainService:
     def start(self) -> None:
         if self._thread and self._thread.is_alive():
             return
+        compat = _win_probe()
+        self._notify({"type": "log", "text": f"Host: {compat.summary()}"})
+        if not compat.has_net_cmdlets:
+            self._notify({
+                "type": "log",
+                "text": (
+                    "Legacy PowerShell detected — MAC spoof / IPv6 disable / "
+                    "hostname spoof unavailable on this host. Proxy chain + "
+                    "kill-switch + WebRTC policy still work."
+                ),
+            })
         self._stop.clear()
         self._thread = threading.Thread(
             target=self._run_thread, name="ChainService", daemon=True
@@ -419,7 +437,9 @@ class ChainService:
             "text": f"Exit IP check through local proxy (≤{int(timeout * 2 + 5)}s)…",
         })
         t0 = time.monotonic()
-        exit_ip = await check_chain_exit_ip(local_proxy, self._settings.ip_check_url, timeout)
+        exit_ip = await check_chain_exit_ip(
+            local_proxy, self._settings.ip_check_url, timeout, chain_hops=len(chain)
+        )
         log.debug("Initial exit IP check took %.2fs → %s", time.monotonic() - t0, exit_ip or "none")
 
         if not exit_ip:
@@ -448,12 +468,34 @@ class ChainService:
         self._notify({"type": "hops", "hops": chain, "status": "healthy", "exit_ip": exit_ip})
         self._notify({"type": "log", "text": f"✓ Chain healthy — Exit IP: {exit_ip}"})
         self._notify({"type": "phase", "phase": "running"})
+        # Pre-flight: surface Group Policy locks (they will override us).
+        pol_before = detect_policy_overrides()
+        if pol_before:
+            self._notify({"type": "log", "text": (
+                f"Group Policy proxy lock detected ({len(pol_before)} entries) — "
+                "these BEAT our settings. Browsers will keep the policy proxy "
+                "(or DIRECT) until those keys are removed."
+            )})
+            for p in pol_before[:3]:
+                self._notify({"type": "log", "text": f"  ! {p}"})
+
         set_system_proxy(
             self._settings.local_host,
             self._settings.local_port,
             self._settings.proxy_bypass,
         )
-        self._notify({"type": "log", "text": f"System proxy → {self._settings.listen_addr()}"})
+        applied = is_system_proxy_set()
+        self._notify({
+            "type": "log",
+            "text": (
+                f"System proxy → {self._settings.listen_addr()} "
+                f"(HKCU + HKLM(adm) + Connections + WinHTTP) "
+                f"{'OK' if applied else 'FAILED — registry write rejected'}"
+            ),
+        })
+        # Post-flight diagnostic — every layer's actual state.
+        for ln in diagnose_system_proxy():
+            self._notify({"type": "log", "text": f"  proxy: {ln}"})
 
         # ── Health monitor loop ───────────────────────────────────────────────
         hc = int(self._settings.health_check_seconds)
@@ -470,7 +512,9 @@ class ChainService:
 
             self._notify({"type": "log", "text": "Health check..."})
             t1 = time.monotonic()
-            exit_ip = await check_chain_exit_ip(local_proxy, self._settings.ip_check_url, timeout)
+            exit_ip = await check_chain_exit_ip(
+                local_proxy, self._settings.ip_check_url, timeout, chain_hops=len(chain)
+            )
             log.debug("Periodic exit IP check %.2fs → %s", time.monotonic() - t1, exit_ip or "none")
 
             if is_chain_leak(exit_ip, real_ip, self._vpn.active):

proxy_chain_manager/sysproxy.py

@@ -1,16 +1,62 @@
-"""Set / clear the Windows system-wide HTTP proxy via the registry + WinINet broadcast."""
+"""Set / clear the Windows system-wide HTTP proxy.
+
+Layers configured so the proxy actually applies system-wide:
+
+1. ``HKCU\\…\\Internet Settings``       — simple values WinINet reads first
+2. ``Internet Settings\\Connections\\DefaultConnectionSettings`` binary blob —
+   overrides #1 for any process that opens the per-connection structure.
+3. ``HKLM\\…\\Internet Settings`` mirror (Admin only) — required on Server when
+   ``ProxySettingsPerUser=0`` is set by Group Policy / baseline image.
+4. ``netsh winhttp set proxy``         — .NET, Windows Update, services and
+   headless browser components that bypass WinINet.
+
+We also actively detect and warn about:
+- ``ProxySettingsPerUser=0``  → HKCU is ignored; we fix it when Admin.
+- Group Policy proxy keys     → those override us; we surface the path so the
+  user can verify or remove them.
+- ``AutoConfigURL`` / ``AutoDetect`` (WPAD) → wiped on engage.
+"""
 from __future__ import annotations
 
 import ctypes
 import logging
+import struct
+import subprocess
 import winreg
 
 log = logging.getLogger(__name__)
 
 _KEY_PATH = r"Software\Microsoft\Windows\CurrentVersion\Internet Settings"
+_CONN_KEY_PATH = (
+    r"Software\Microsoft\Windows\CurrentVersion\Internet Settings\Connections"
+)
+_HKLM_INET_PATH = r"SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings"
+_HKLM_CONN_PATH = (
+    r"SOFTWARE\Microsoft\Windows\CurrentVersion\Internet Settings\Connections"
+)
+_POLICY_PATHS = (
+    (winreg.HKEY_LOCAL_MACHINE,
+     r"SOFTWARE\Policies\Microsoft\Windows\CurrentVersion\Internet Settings"),
+    (winreg.HKEY_CURRENT_USER,
+     r"SOFTWARE\Policies\Microsoft\Windows\CurrentVersion\Internet Settings"),
+    (winreg.HKEY_LOCAL_MACHINE,
+     r"SOFTWARE\Policies\Microsoft\Internet Explorer\Control Panel"),
+)
 _SETTINGS_CHANGED = 39
 _REFRESH = 37
 
+_FLAG_DIRECT       = 0x01
+_FLAG_MANUAL_PROXY = 0x02
+_FLAG_AUTO_CONFIG  = 0x04
+_FLAG_AUTO_DETECT  = 0x08
+
+
+def _is_admin() -> bool:
+    try:
+        return ctypes.windll.shell32.IsUserAnAdmin() != 0  # type: ignore[attr-defined]
+    except Exception:
+        return False
+
 
 def _broadcast() -> None:
     """Tell running apps (browsers, etc.) that proxy settings changed."""
@@ -22,8 +68,281 @@ def _broadcast() -> None:
         pass
 
 
-def set_system_proxy(host: str, port: int, bypass: str = "localhost;127.*;10.*;192.168.*;<local>") -> None:
+def _bump_counter(prev: bytes | None) -> int:
+    if not prev or len(prev) < 8:
+        return 1
+    try:
+        return int.from_bytes(prev[4:8], "little") + 1
+    except Exception:
+        return 1
+
+
+def _build_blob(
+    proxy: str,
+    bypass: str,
+    auto_config_url: str = "",
+    counter: int = 1,
+) -> bytes:
+    """REG_BINARY layout for DefaultConnectionSettings (little-endian)."""
+    flags = _FLAG_DIRECT
+    if proxy:
+        flags |= _FLAG_MANUAL_PROXY
+    if auto_config_url:
+        flags |= _FLAG_AUTO_CONFIG
+
+    p = proxy.encode("utf-8")
+    b = bypass.encode("utf-8")
+    a = auto_config_url.encode("utf-8")
+
+    return (
+        struct.pack("<III", 0x46, counter, flags)
+        + struct.pack("<I", len(p)) + p
+        + struct.pack("<I", len(b)) + b
+        + struct.pack("<I", len(a)) + a
+        + b"\x00" * 32
+    )
+
+
+def _read_blob_counter(hive: int, path: str) -> int:
+    try:
+        with winreg.OpenKey(hive, path, 0, winreg.KEY_QUERY_VALUE) as key:
+            val, _ = winreg.QueryValueEx(key, "DefaultConnectionSettings")
+            return _bump_counter(val)
+    except OSError:
+        return 1
+
+
+def _write_conn_blob(hive: int, path: str, proxy: str, bypass: str) -> bool:
+    counter = _read_blob_counter(hive, path)
+    blob = _build_blob(proxy, bypass, "", counter)
+    try:
+        key = winreg.CreateKeyEx(hive, path, 0, winreg.KEY_SET_VALUE)
+        with key:
+            winreg.SetValueEx(key, "DefaultConnectionSettings", 0, winreg.REG_BINARY, blob)
+            winreg.SetValueEx(key, "SavedLegacySettings", 0, winreg.REG_BINARY, blob)
+        return True
+    except OSError as e:
+        log.debug("Connections blob write failed (%s): %s", path, e)
+        return False
+
+
+def _clear_conn_blob(hive: int, path: str) -> None:
+    counter = _read_blob_counter(hive, path)
+    blob = _build_blob("", "", "", counter)
+    try:
+        with winreg.OpenKey(hive, path, 0, winreg.KEY_SET_VALUE) as key:
+            winreg.SetValueEx(key, "DefaultConnectionSettings", 0, winreg.REG_BINARY, blob)
+            winreg.SetValueEx(key, "SavedLegacySettings", 0, winreg.REG_BINARY, blob)
+    except OSError:
+        pass
+
+
+def _wipe_autoconfig(key: winreg.HKEYType) -> None:
+    for name in ("AutoConfigURL", "AutoDetect"):
+        try:
+            winreg.DeleteValue(key, name)
+        except OSError:
+            pass
+
+
+def _set_winhttp_proxy(host: str, port: int, bypass: str) -> None:
+    try:
+        bypass_list = (
+            bypass.replace(";", " ").replace("<local>", "<local>").strip()
+        ) or "<local>"
+        subprocess.run(
+            ["netsh", "winhttp", "set", "proxy",
+             f"{host}:{port}", f"bypass-list={bypass_list}"],
+            capture_output=True, text=True, timeout=15,
+            creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
+        )
+    except Exception as e:
+        log.debug("netsh winhttp set proxy failed: %s", e)
+
+
+def _reset_winhttp_proxy() -> None:
+    try:
+        subprocess.run(
+            ["netsh", "winhttp", "reset", "proxy"],
+            capture_output=True, text=True, timeout=15,
+            creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
+        )
+    except Exception:
+        pass
+
+
+def _read_proxy_settings_per_user() -> int | None:
+    """``HKLM\\…\\Internet Settings\\ProxySettingsPerUser``.
+
+    When 0, Windows ignores HKCU proxy values and reads only HKLM. Set on many
+    Server images and AD policy baselines — the #1 cause of "set the proxy but
+    the browser still goes direct" on Server.
+    """
+    try:
+        with winreg.OpenKey(
+            winreg.HKEY_LOCAL_MACHINE, _HKLM_INET_PATH, 0, winreg.KEY_QUERY_VALUE
+        ) as key:
+            val, _ = winreg.QueryValueEx(key, "ProxySettingsPerUser")
+            return int(val)
+    except OSError:
+        return None
+
+
+def _fix_proxy_settings_per_user() -> bool:
+    """Force ``ProxySettingsPerUser=1`` (per-user proxy honored). Admin only."""
+    if not _is_admin():
+        return False
+    try:
+        with winreg.CreateKeyEx(
+            winreg.HKEY_LOCAL_MACHINE, _HKLM_INET_PATH, 0, winreg.KEY_SET_VALUE
+        ) as key:
+            winreg.SetValueEx(key, "ProxySettingsPerUser", 0, winreg.REG_DWORD, 1)
+        log.info("HKLM\\…\\ProxySettingsPerUser → 1 (was %s)", _read_proxy_settings_per_user())
+        return True
+    except OSError as e:
+        log.warning("Could not fix ProxySettingsPerUser: %s", e)
+        return False
+
+
+def _set_hklm_root(proxy: str, bypass: str) -> bool:
+    """Mirror the per-user keys at HKLM so machine-scope WinINet reads honor us."""
+    if not _is_admin():
+        return False
+    try:
+        with winreg.CreateKeyEx(
+            winreg.HKEY_LOCAL_MACHINE, _HKLM_INET_PATH, 0, winreg.KEY_SET_VALUE
+        ) as key:
+            winreg.SetValueEx(key, "ProxyEnable", 0, winreg.REG_DWORD, 1)
+            winreg.SetValueEx(key, "ProxyServer", 0, winreg.REG_SZ, proxy)
+            winreg.SetValueEx(key, "ProxyOverride", 0, winreg.REG_SZ, bypass)
+            _wipe_autoconfig(key)
+        return True
+    except OSError as e:
+        log.warning("HKLM root proxy write failed: %s", e)
+        return False
+
+
+def _clear_hklm_root() -> None:
+    if not _is_admin():
+        return
+    try:
+        with winreg.OpenKey(
+            winreg.HKEY_LOCAL_MACHINE, _HKLM_INET_PATH, 0, winreg.KEY_SET_VALUE
+        ) as key:
+            winreg.SetValueEx(key, "ProxyEnable", 0, winreg.REG_DWORD, 0)
+            _wipe_autoconfig(key)
+    except OSError:
+        pass
+
+
+def detect_policy_overrides() -> list[str]:
+    """Return human-readable paths of Group Policy proxy locks that beat us.
+
+    Anything we find here will silently override our manual proxy. We do *not*
+    delete policy keys (admins set those deliberately) — we just surface them.
+    """
+    hits: list[str] = []
+    proxy_value_names = ("ProxyServer", "ProxyEnable", "AutoConfigURL", "ProxyOverride")
+    for hive, path in _POLICY_PATHS:
+        try:
+            with winreg.OpenKey(hive, path, 0, winreg.KEY_QUERY_VALUE) as key:
+                for n in proxy_value_names:
+                    try:
+                        winreg.QueryValueEx(key, n)
+                        hive_name = "HKLM" if hive == winreg.HKEY_LOCAL_MACHINE else "HKCU"
+                        hits.append(f"{hive_name}\\{path}\\{n}")
+                    except OSError:
+                        continue
+        except OSError:
+            continue
+    return hits
+
+
+def _read_str(hive: int, path: str, name: str) -> str:
+    try:
+        with winreg.OpenKey(hive, path, 0, winreg.KEY_QUERY_VALUE) as key:
+            val, _ = winreg.QueryValueEx(key, name)
+            return str(val)
+    except OSError:
+        return ""
+
+
+def _read_dword(hive: int, path: str, name: str) -> int | None:
+    try:
+        with winreg.OpenKey(hive, path, 0, winreg.KEY_QUERY_VALUE) as key:
+            val, _ = winreg.QueryValueEx(key, name)
+            return int(val)
+    except OSError:
+        return None
+
+
+def _read_winhttp_proxy() -> str:
+    try:
+        r = subprocess.run(
+            ["netsh", "winhttp", "show", "proxy"],
+            capture_output=True, text=True, timeout=10,
+            creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
+        )
+        for ln in (r.stdout or "").splitlines():
+            if "proxy" in ln.lower() and ":" in ln:
+                return ln.strip()
+        return (r.stdout or "").strip().splitlines()[-1] if r.stdout else ""
+    except Exception:
+        return ""
+
+
+def diagnose_system_proxy() -> list[str]:
+    """Return a list of human-readable lines covering every place proxy can
+    be configured. Logged on each engage so "chain green but browser leaks"
+    is debuggable without RegEdit gymnastics.
+    """
+    lines: list[str] = []
+    per_user = _read_proxy_settings_per_user()
+    per_user_msg = (
+        "1 (HKCU honored)" if per_user == 1
+        else "0 (HKCU IGNORED — Server lock!)" if per_user == 0
+        else "(unset → defaults to HKCU)"
+    )
+    lines.append(f"ProxySettingsPerUser = {per_user_msg}")
+
+    en_u = _read_dword(winreg.HKEY_CURRENT_USER, _KEY_PATH, "ProxyEnable")
+    ps_u = _read_str(winreg.HKEY_CURRENT_USER, _KEY_PATH, "ProxyServer")
+    lines.append(f"HKCU  Enable={en_u}  Server='{ps_u}'")
+
+    en_m = _read_dword(winreg.HKEY_LOCAL_MACHINE, _HKLM_INET_PATH, "ProxyEnable")
+    ps_m = _read_str(winreg.HKEY_LOCAL_MACHINE, _HKLM_INET_PATH, "ProxyServer")
+    lines.append(f"HKLM  Enable={en_m}  Server='{ps_m}'")
+
+    ac_u = _read_str(winreg.HKEY_CURRENT_USER, _KEY_PATH, "AutoConfigURL")
+    ad_u = _read_dword(winreg.HKEY_CURRENT_USER, _KEY_PATH, "AutoDetect")
+    if ac_u or ad_u:
+        lines.append(f"WPAD/PAC: AutoConfigURL='{ac_u}' AutoDetect={ad_u}")
+
+    winhttp = _read_winhttp_proxy()
+    if winhttp:
+        lines.append(f"WinHTTP: {winhttp}")
+
+    pol = detect_policy_overrides()
+    if pol:
+        lines.append(f"Policy overrides (these BEAT us): {len(pol)} entries")
+        for p in pol[:5]:
+            lines.append(f"  ! {p}")
+        if len(pol) > 5:
+            lines.append(f"  ! …and {len(pol) - 5} more")
+    else:
+        lines.append("Policy overrides: none")
+
+    return lines
+
+
+def set_system_proxy(
+    host: str,
+    port: int,
+    bypass: str = "localhost;127.*;10.*;192.168.*;<local>",
+) -> None:
     proxy = f"{host}:{port}"
+
+    # HKCU root
     try:
         with winreg.OpenKey(
             winreg.HKEY_CURRENT_USER, _KEY_PATH, 0, winreg.KEY_SET_VALUE
@@ -31,10 +350,40 @@ def set_system_proxy(host: str, port: int, bypass: str = "localhost;127.*;10.*;1
             winreg.SetValueEx(key, "ProxyEnable", 0, winreg.REG_DWORD, 1)
             winreg.SetValueEx(key, "ProxyServer", 0, winreg.REG_SZ, proxy)
             winreg.SetValueEx(key, "ProxyOverride", 0, winreg.REG_SZ, bypass)
-        _broadcast()
+            _wipe_autoconfig(key)
-        log.info("System proxy set to %s (bypass: %s)", proxy, bypass)
     except OSError:
-        log.exception("Failed to set system proxy")
+        log.exception("Failed to set system proxy (HKCU root)")
+        return
+
+    _write_conn_blob(winreg.HKEY_CURRENT_USER, _CONN_KEY_PATH, proxy, bypass)
+
+    # If ProxySettingsPerUser=0 (Server / GPO baseline), HKCU is ignored.
+    # When Admin, fix the flag AND mirror to HKLM so the proxy actually applies.
+    per_user = _read_proxy_settings_per_user()
+    if per_user == 0:
+        log.warning(
+            "ProxySettingsPerUser=0 detected — Windows is ignoring per-user "
+            "proxy. Attempting Admin fix (HKLM mirror)."
+        )
+        if _is_admin():
+            _fix_proxy_settings_per_user()
+            _set_hklm_root(proxy, bypass)
+            _write_conn_blob(winreg.HKEY_LOCAL_MACHINE, _HKLM_CONN_PATH, proxy, bypass)
+        else:
+            log.warning(
+                "Not running as Admin — cannot fix ProxySettingsPerUser. "
+                "Re-launch elevated for proxy to apply on this Server image."
+            )
+
+    # On Admin runs always mirror HKLM root too. Harmless when PerUser=1 and
+    # correct when PerUser=0 or absent.
+    if _is_admin():
+        _set_hklm_root(proxy, bypass)
+        _write_conn_blob(winreg.HKEY_LOCAL_MACHINE, _HKLM_CONN_PATH, proxy, bypass)
+
+    _set_winhttp_proxy(host, port, bypass)
+    _broadcast()
+    log.info("System proxy set %s (bypass=%s) — HKCU + HKLM(adm) + Connections + WinHTTP", proxy, bypass)
 
 
 def clear_system_proxy() -> None:
@@ -43,11 +392,18 @@ def clear_system_proxy() -> None:
             winreg.HKEY_CURRENT_USER, _KEY_PATH, 0, winreg.KEY_SET_VALUE
         ) as key:
             winreg.SetValueEx(key, "ProxyEnable", 0, winreg.REG_DWORD, 0)
-        _broadcast()
+            _wipe_autoconfig(key)
-        log.info("System proxy cleared")
     except OSError:
         log.exception("Failed to clear system proxy")
 
+    _clear_conn_blob(winreg.HKEY_CURRENT_USER, _CONN_KEY_PATH)
+    if _is_admin():
+        _clear_hklm_root()
+        _clear_conn_blob(winreg.HKEY_LOCAL_MACHINE, _HKLM_CONN_PATH)
+    _reset_winhttp_proxy()
+    _broadcast()
+    log.info("System proxy cleared — HKCU + HKLM(adm) + Connections + WinHTTP")
+
 
 def is_system_proxy_set() -> bool:
     try:

proxy_chain_manager/validator.py

@@ -10,8 +10,16 @@ import httpx
 
 log = logging.getLogger(__name__)
 
-# Secondary fallback endpoints for IP resolution
+# Secondary fallback endpoints for IP resolution.
+# HTTP endpoints come first: many free proxies and older Windows Server
+# environments fail HTTPS CONNECT through chained hops. Plain HTTP IP-check
+# succeeds even when only forward-proxying (no CONNECT) works, so the chain's
+# "last leg" exit-IP verification doesn't fail just because TLS can't tunnel.
 _IP_FALLBACKS = [
+    "http://api.ipify.org/?format=json",
+    "http://checkip.amazonaws.com/",
+    "http://ip-api.com/json/",
+    "http://ifconfig.me/ip",
     "https://api.ipify.org?format=json",
     "https://httpbin.org/ip",
     "https://ifconfig.me/ip",
@@ -144,14 +152,25 @@ async def check_chain_exit_ip(
     listen_proxy: str,
     check_url: str,
     timeout_seconds: float,
+    chain_hops: int = 3,
 ) -> str | None:
     """Query the IP-check URL through the local chain proxy.
-    Bounded total time — never stacks one slow request per fallback URL forever."""
+
-    per = max(5.0, min(20.0, float(timeout_seconds)))
+    Bounded total time — never stacks one slow request per fallback URL forever.
-    budget = max(15.0, min(60.0, float(timeout_seconds) * 2 + 5.0))
+    Per-request timeout scales mildly with chain length so 5+ hop chains on
-    urls = [check_url] + [u for u in _IP_FALLBACKS if u != check_url][:2]
+    slower hardware (older Windows Server, low-spec VPS) don't time out on
+    cumulative TLS/CONNECT handshakes.
+    """
+    hops = max(1, int(chain_hops))
+    scale = 1.0 + max(0, hops - 3) * 0.35
+    per = max(5.0, min(30.0, float(timeout_seconds) * scale))
+    budget = max(20.0, min(90.0, float(timeout_seconds) * 2 * scale + 5.0))
+    # Try more endpoints with HTTP first; if any hop blocks CONNECT, HTTPS
+    # IP-check would fail and the whole chain looks "dead" at the last step.
+    urls = [check_url] + [u for u in _IP_FALLBACKS if u != check_url][:4]
     log.debug(
-        "check_chain_exit_ip: budget=%.1fs per_req=%.1fs fallback_count=%d",
+        "check_chain_exit_ip: hops=%d budget=%.1fs per_req=%.1fs fallback_count=%d",
+        hops,
         budget,
         per,
         len(urls),

proxy_chain_manager/vpn_detect.py

@@ -16,7 +16,15 @@ _VPN_ADAPTER_HINTS = (
     "tailscale", "zerotier", "cisco anyconnect", "fortinet", "pulse secure",
     "globalprotect", "softether", "proton", "mullvad", "expressvpn",
     "surfshark", "private internet", "pia ", "windscribe", "hotspot shield",
-    "tunnel", "vpn",
+)
+
+_NON_VPN_HINTS = (
+    "wan miniport",
+    "microsoft kernel debug",
+    "isatap",
+    "teredo",
+    "loopback",
+    "pseudo-interface",
 )
 
 # Executables to whitelist in kill-switch when present
@@ -97,10 +105,45 @@ def detect_vpn() -> VpnStatus:
     """Inspect up network adapters for VPN/tunnel interfaces."""
     out = _run_ps(
         "Get-NetAdapter | Where-Object { $_.Status -eq 'Up' } | "
-        "Select-Object -ExpandProperty Name"
+        "ForEach-Object { \"$($_.Name)|$($_.InterfaceDescription)\" }"
     )
     if not out:
-        # Fallback: netsh
+        # Fallback for PowerShell 2.0 / older Windows Server: parse "wmic nic"
+        # then "netsh interface show interface". Both are locale-tolerant.
+        try:
+            r = subprocess.run(
+                ["wmic", "nic", "where", "NetEnabled=true",
+                 "get", "NetConnectionID,Name", "/format:list"],
+                capture_output=True,
+                text=True,
+                timeout=12,
+                creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
+            )
+            blob = (r.stdout or "")
+            names: list[str] = []
+            cur_id = ""
+            cur_name = ""
+            for ln in blob.splitlines():
+                ln = ln.strip()
+                if not ln:
+                    if cur_id:
+                        names.append(f"{cur_id}|{cur_name}")
+                    cur_id, cur_name = "", ""
+                    continue
+                if ln.startswith("NetConnectionID="):
+                    cur_id = ln.split("=", 1)[1].strip()
+                elif ln.startswith("Name="):
+                    cur_name = ln.split("=", 1)[1].strip()
+            if cur_id:
+                names.append(f"{cur_id}|{cur_name}")
+            out = "\n".join(names)
+        except Exception:
+            out = ""
+
+    if not out:
+        # Last-ditch: netsh. Locale-tolerant — match the connected/enabled state
+        # by extracting the interface name from the rightmost column. Older
+        # localized Server SKUs (es, de, fr, etc.) don't print literal "Enabled".
         try:
             r = subprocess.run(
                 ["netsh", "interface", "show", "interface"],
@@ -109,25 +152,42 @@ def detect_vpn() -> VpnStatus:
                 timeout=10,
                 creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
             )
-            lines = (r.stdout or "").splitlines()
+            raw = (r.stdout or "")
             names = []
-            for ln in lines[3:]:
+            for ln in raw.splitlines():
-                parts = ln.split()
+                s = ln.rstrip()
-                if len(parts) >= 4 and parts[0] == "Enabled":
+                if not s or s.startswith("-") or ":" in s.split(" ")[0]:
-                    names.append(" ".join(parts[3:]))
+                    continue
+                parts = re.split(r"\s{2,}", s.strip())
+                if len(parts) >= 4:
+                    nm = parts[-1].strip()
+                    if nm and nm.lower() not in ("interface name", "nombre de interfaz"):
+                        names.append(f"{nm}|")
             out = "\n".join(names)
         except Exception:
             return VpnStatus()
 
     adapters: list[str] = []
+    adapter_blob: list[str] = []
     for line in out.splitlines():
-        name = line.strip()
+        raw = line.strip()
+        if not raw:
+            continue
+        if "|" in raw:
+            name, desc = raw.split("|", 1)
+        else:
+            name, desc = raw, ""
+        name = name.strip()
+        desc = desc.strip()
         if name:
             adapters.append(name)
+            adapter_blob.append((name + " " + desc).strip())
 
     hits: list[str] = []
-    for name in adapters:
+    for i, name in enumerate(adapters):
-        low = name.lower()
+        low = adapter_blob[i].lower()
+        if any(h in low for h in _NON_VPN_HINTS):
+            continue
         if any(h in low for h in _VPN_ADAPTER_HINTS):
             hits.append(name)
 

proxy_chain_manager/win_compat.py

@@ -0,0 +1,90 @@
+"""Windows version / PowerShell capability probe.
+
+Used by privacy features to log a single clear reason when a function silently
+no-ops on older Windows Server hosts (Server 2008 R2 ships PowerShell 2.0 which
+does not have ``Get-NetAdapter`` / ``Set-NetAdapter`` / ``Disable-NetAdapterBinding``
+/ ``Get-DnsClientServerAddress`` / ``Rename-Computer``).
+"""
+from __future__ import annotations
+
+import logging
+import platform
+import subprocess
+from dataclasses import dataclass
+from functools import lru_cache
+
+log = logging.getLogger(__name__)
+
+
+@dataclass(frozen=True)
+class WinCompat:
+    release: str           # e.g. "10", "2012ServerR2"
+    build: int             # major build number
+    powershell_major: int  # 0 = PowerShell not detected
+    has_net_cmdlets: bool  # Get-NetAdapter etc. (PS 3.0+ on Server 2012+)
+    has_defender: bool     # Add-MpPreference cmdlet exists
+
+    def summary(self) -> str:
+        return (
+            f"Windows release={self.release} build={self.build} "
+            f"PowerShell={self.powershell_major}.x "
+            f"NetAdapter cmdlets={'yes' if self.has_net_cmdlets else 'no'} "
+            f"Defender={'yes' if self.has_defender else 'no'}"
+        )
+
+
+def _powershell_major() -> int:
+    try:
+        r = subprocess.run(
+            ["powershell", "-NoProfile", "-NonInteractive", "-Command",
+             "$PSVersionTable.PSVersion.Major"],
+            capture_output=True,
+            text=True,
+            timeout=12,
+            creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
+        )
+        out = (r.stdout or "").strip().splitlines()[-1] if r.stdout else ""
+        return int(out) if out.isdigit() else 0
+    except Exception:
+        return 0
+
+
+def _has_cmdlet(name: str) -> bool:
+    try:
+        r = subprocess.run(
+            ["powershell", "-NoProfile", "-NonInteractive", "-Command",
+             f"if (Get-Command {name} -ErrorAction SilentlyContinue) "
+             f"{{ 'yes' }} else {{ 'no' }}"],
+            capture_output=True,
+            text=True,
+            timeout=10,
+            creationflags=getattr(subprocess, "CREATE_NO_WINDOW", 0),
+        )
+        return "yes" in (r.stdout or "").lower()
+    except Exception:
+        return False
+
+
+@lru_cache(maxsize=1)
+def probe() -> WinCompat:
+    """Cached host probe. Cheap on subsequent calls."""
+    release = platform.release()
+    try:
+        build = int(platform.version().split(".")[-1])
+    except Exception:
+        build = 0
+    ps = _powershell_major()
+    # PowerShell >= 3.0 is the gate for the modern Net* cmdlets that all the
+    # privacy features rely on. Anything older (Server 2008 R2 RTM) only has
+    # PS 2.0 and needs WMI / netsh / ipconfig fallbacks.
+    has_net = ps >= 3 and _has_cmdlet("Get-NetAdapter")
+    has_def = _has_cmdlet("Add-MpPreference")
+    info = WinCompat(
+        release=release,
+        build=build,
+        powershell_major=ps,
+        has_net_cmdlets=has_net,
+        has_defender=has_def,
+    )
+    log.info("WinCompat probe: %s", info.summary())
+    return info

tests/test_proxy_god.py

@@ -10,6 +10,7 @@ from proxy_chain_manager.config import (
     Settings,
     merge_proxy_credentials,
     normalize_proxy_url,
+    parse_exit_proxy_input,
     redact_proxy_url,
     sanitize_settings,
     split_proxy_for_edit,
@@ -87,6 +88,45 @@ class TestConfig(unittest.TestCase):
         self.assertTrue(changed)
         self.assertGreater(len(s2.sources), 0)
 
+    def test_parse_exit_host_port_only_defaults_to_socks5(self) -> None:
+        base, u, pw = parse_exit_proxy_input("1.2.3.4:1080")
+        self.assertEqual(base, "socks5://1.2.3.4:1080")
+        self.assertEqual(u, "")
+        self.assertEqual(pw, "")
+
+    def test_parse_exit_colon_quadruple(self) -> None:
+        base, u, pw = parse_exit_proxy_input("1.2.3.4:1080:alice:s3cret")
+        self.assertEqual(base, "socks5://1.2.3.4:1080")
+        self.assertEqual(u, "alice")
+        self.assertEqual(pw, "s3cret")
+
+    def test_parse_exit_password_with_colon_kept_intact(self) -> None:
+        base, u, pw = parse_exit_proxy_input("h:9:u:a:b:c")
+        self.assertEqual(base, "socks5://h:9")
+        self.assertEqual(u, "u")
+        self.assertEqual(pw, "a:b:c")
+
+    def test_parse_exit_at_form_no_scheme(self) -> None:
+        base, u, pw = parse_exit_proxy_input("alice:secret@1.2.3.4:1080")
+        self.assertEqual(base, "socks5://1.2.3.4:1080")
+        self.assertEqual(u, "alice")
+        self.assertEqual(pw, "secret")
+
+    def test_parse_exit_respects_explicit_scheme(self) -> None:
+        base, u, pw = parse_exit_proxy_input("http://x:y@9.9.9.9:8080")
+        self.assertEqual(base, "http://9.9.9.9:8080")
+        self.assertEqual(u, "x")
+        self.assertEqual(pw, "y")
+
+    def test_parse_exit_whitespace_form(self) -> None:
+        base, u, pw = parse_exit_proxy_input("1.2.3.4:1080 alice s3cret")
+        self.assertEqual(base, "socks5://1.2.3.4:1080")
+        self.assertEqual(u, "alice")
+        self.assertEqual(pw, "s3cret")
+
+    def test_parse_exit_empty(self) -> None:
+        self.assertEqual(parse_exit_proxy_input("   "), ("", "", ""))
+
     def test_sanitize_clamps_extremes(self) -> None:
         s = Settings(
             chain_length=0,