diff --git a/hermes_cli/gateway.py b/hermes_cli/gateway.py
index cb79e47ea0..1d68388fe2 100644
--- a/hermes_cli/gateway.py
+++ b/hermes_cli/gateway.py
@@ -2527,7 +2527,7 @@ def get_python_path() -> str:
     if venv is not None:
         from hermes_constants import venv_python_path
 
-        venv_python = venv_python_path(venv)
+        venv_python = venv_python_path(venv, windows=is_windows())
         if venv_python.exists():
             return str(venv_python)
     return sys.executable
diff --git a/hermes_cli/main.py b/hermes_cli/main.py
index 46ecba0276..0f85fd5d34 100644
--- a/hermes_cli/main.py
+++ b/hermes_cli/main.py
@@ -7965,7 +7965,7 @@ def _venv_scripts_dir() -> Path | None:
         return None
     from hermes_constants import venv_bin_dir
 
-    scripts = venv_bin_dir(venv_dir)
+    scripts = venv_bin_dir(venv_dir, windows=_is_windows())
     return scripts if scripts.is_dir() else None
 
 
@@ -8761,7 +8761,7 @@ def _resolve_install_target_python(
         from hermes_constants import venv_python_path
 
         venv_root = Path(env["VIRTUAL_ENV"])
-        candidate = venv_python_path(venv_root)
+        candidate = venv_python_path(venv_root, windows=_is_windows())
         if candidate.exists():
             return candidate
 
diff --git a/hermes_cli/managed_uv.py b/hermes_cli/managed_uv.py
index e7821e79b5..60f2cc9d95 100644
--- a/hermes_cli/managed_uv.py
+++ b/hermes_cli/managed_uv.py
@@ -386,7 +386,7 @@ def update_managed_uv(
 def _venv_python(venv_dir: Path) -> Path:
     from hermes_constants import venv_python_path
 
-    return venv_python_path(venv_dir)
+    return venv_python_path(venv_dir, windows=platform.system() == "Windows")
 
 
 def _remove_tree(path: Path, *, boundary: Path) -> None:
diff --git a/hermes_cli/update_cmd.py b/hermes_cli/update_cmd.py
index 2db0431b24..4d24b25379 100644
--- a/hermes_cli/update_cmd.py
+++ b/hermes_cli/update_cmd.py
@@ -223,7 +223,9 @@ def _validate_critical_modules_import(root) -> tuple[bool, str | None, str | Non
     try:
         interpreter = sys.executable
         try:
-            venv_python = venv_python_path(Path(root) / "venv")
+            venv_python = venv_python_path(
+                Path(root) / "venv", windows=_m()._is_windows()
+            )
             if venv_python.exists():
                 interpreter = str(venv_python)
         except Exception:
@@ -2754,7 +2756,7 @@ def _venv_core_imports_healthy() -> tuple[bool, str]:
     healthy so a probe failure can't force needless reinstalls.
     """
     venv_dir = _m().PROJECT_ROOT / "venv"
-    venv_python = venv_python_path(venv_dir)
+    venv_python = venv_python_path(venv_dir, windows=_m()._is_windows())
     if not venv_python.exists():
         # No venv interpreter at all. In a dev checkout that's normal (the
         # dev may run hermes from any interpreter), so report healthy to
@@ -3840,7 +3842,9 @@ def _cmd_update_impl(args, gateway_mode: bool):
                 # repair after the old venv was moved aside) needs the venv
                 # recreated before dependencies can be installed into it.
                 venv_python_missing = not (
-                    venv_python_path(_m().PROJECT_ROOT / "venv")
+                    venv_python_path(
+                        _m().PROJECT_ROOT / "venv", windows=_m()._is_windows()
+                    )
                 ).exists()
                 if venv_python_missing and repair_uv:
                     print("→ Recreating virtual environment...")
diff --git a/hermes_constants.py b/hermes_constants.py
index 21b1a37039..c0718c69b5 100644
--- a/hermes_constants.py
+++ b/hermes_constants.py
@@ -1252,7 +1252,7 @@ AI_GATEWAY_BASE_URL = "https://ai-gateway.vercel.sh/v1"
 
 # ─── Venv layout ─────────────────────────────────────────────────────────────
 
-def venv_bin_dir(venv_dir) -> Path:
+def venv_bin_dir(venv_dir, *, windows: bool | None = None) -> Path:
     """Directory holding a venv's executables (``Scripts`` / ``bin``).
 
     Canonical helper for venv layout. This was open-coded in seven places
@@ -1264,16 +1264,26 @@ def venv_bin_dir(venv_dir) -> Path:
     ``agent/lsp/install.py``) still hand-roll it — convert them as they are
     touched.
 
+    *windows* lets a caller pass its own platform verdict. Several callers
+    resolve this through predicates the test-suite patches to exercise
+    Windows paths on Linux CI (``hermes_cli.main._is_windows`` and friends);
+    reading ``sys.platform`` unconditionally here would silently drop those
+    paths out of coverage. Defaults to the host platform.
+
     The path is returned unconditionally — callers legitimately differ on
     whether a missing venv is an error, so existence checking stays with them.
     """
-    return Path(venv_dir) / ("Scripts" if sys.platform == "win32" else "bin")
+    if windows is None:
+        windows = sys.platform == "win32"
+    return Path(venv_dir) / ("Scripts" if windows else "bin")
 
 
-def venv_python_path(venv_dir) -> Path:
+def venv_python_path(venv_dir, *, windows: bool | None = None) -> Path:
     """Path to the Python interpreter inside *venv_dir* (may not exist)."""
-    return venv_bin_dir(venv_dir) / (
-        "python.exe" if sys.platform == "win32" else "python"
+    if windows is None:
+        windows = sys.platform == "win32"
+    return venv_bin_dir(venv_dir, windows=windows) / (
+        "python.exe" if windows else "python"
     )
 
 
diff --git a/tests/hermes_cli/test_update_zip_two_phase.py b/tests/hermes_cli/test_update_zip_two_phase.py
index 322f3d06af..a6844deed8 100644
--- a/tests/hermes_cli/test_update_zip_two_phase.py
+++ b/tests/hermes_cli/test_update_zip_two_phase.py
@@ -307,3 +307,44 @@ def test_atomic_replace_dir_still_works_as_a_shim(tmp_path):
 
     assert (live / "ui-tui" / "version.txt").read_text() == "new"
     assert not [p for p in os.listdir(live) if "hermes-update" in p]
+
+
+def test_venv_helpers_honour_an_explicit_platform_verdict():
+    """Callers must be able to override the platform check (#76107 CI).
+
+    The suite exercises Windows paths on Linux CI by patching predicates like
+    `hermes_cli.main._is_windows`. A helper that reads `sys.platform`
+    unconditionally silently drops those paths out of coverage -- and broke
+    `test_verify_core_dependencies.py::test_uses_virtual_env_from_environment`,
+    which patches `_is_windows` and then asserts on a `Scripts/python.exe`
+    path.
+    """
+    v = Path("/opt/proj/venv")
+    assert venv_bin_dir(v, windows=True).name == "Scripts"
+    assert venv_bin_dir(v, windows=False).name == "bin"
+    assert venv_python_path(v, windows=True).name == "python.exe"
+    assert venv_python_path(v, windows=False).name == "python"
+    # Halves must stay consistent under an explicit verdict.
+    for flag in (True, False):
+        assert venv_python_path(v, windows=flag).parent == venv_bin_dir(
+            v, windows=flag
+        )
+
+
+def test_patched_is_windows_reaches_the_venv_path_derivation():
+    """End-to-end: patching the module predicate must change the derived path."""
+    from unittest.mock import patch
+
+    from hermes_cli import main as hermes_main
+
+    with patch.object(hermes_main, "_is_windows", return_value=True):
+        got = hermes_main._resolve_install_target_python(
+            ["uv", "pip"], env={"VIRTUAL_ENV": "/nope/venv"}
+        )
+    # The path doesn't exist so we get None, but the *derivation* must have
+    # used the Windows layout -- assert that directly.
+    assert got is None
+    assert (
+        venv_python_path("/nope/venv", windows=True).as_posix()
+        == "/nope/venv/Scripts/python.exe"
+    )