diff --git a/docs/changelog/+base-probe-env.bugfix.rst b/docs/changelog/+base-probe-env.bugfix.rst
new file mode 100644
index 0000000..9f3c086
--- /dev/null
+++ b/docs/changelog/+base-probe-env.bugfix.rst
@@ -0,0 +1 @@
+Use the supplied environment for base-interpreter probes when resolving a virtual environment.
diff --git a/src/python_discovery/_py_info.py b/src/python_discovery/_py_info.py
index ecf6cc6..a85b4b9 100644
--- a/src/python_discovery/_py_info.py
+++ b/src/python_discovery/_py_info.py
@@ -421,7 +421,7 @@ def _from_exe_with_args(  # ruff:ignore[too-many-arguments]
 
         if isinstance(proposed, PythonInfo) and resolve_to_host:
             try:
-                proposed = proposed.resolve_to_system(cache, proposed)
+                proposed = proposed.resolve_to_system(cache, proposed, env=env)
             except Exception as exception:
                 if raise_on_error:
                     raise
@@ -452,12 +452,15 @@ def from_dict(cls, data: dict[str, InfoValue]) -> PythonInfo:
         return result
 
     @classmethod
-    def resolve_to_system(cls, cache: PyInfoCache | None, target: PythonInfo) -> PythonInfo:
+    def resolve_to_system(
+        cls, cache: PyInfoCache | None, target: PythonInfo, *, env: Mapping[str, str] | None = None
+    ) -> PythonInfo:
         """
         Walk virtualenv/venv prefix chains to find the underlying system interpreter.
 
         :param cache: interpreter metadata cache; when ``None`` results are not cached.
         :param target: the interpreter to resolve.
+        :param env: environment mapping; defaults to :data:`os.environ`.
         """
         start_executable = target.executable
         prefixes = OrderedDict()
@@ -475,9 +478,9 @@ def resolve_to_system(cls, cache: PyInfoCache | None, target: PythonInfo) -> Pyt
                 msg = "prefixes are causing a circle {}".format("|".join(prefixes.keys()))
                 raise RuntimeError(msg)
             prefixes[prefix_key] = target
-            target = target.discover_exe(cache, prefix=prefix, exact=False)
+            target = target.discover_exe(cache, prefix=prefix, exact=False, env=env)
         if target.executable != target.system_executable:
-            resolved = cls.from_exe(target.system_executable, cache)
+            resolved = cls.from_exe(target.system_executable, cache, env=env)
             if resolved is not None:
                 target = resolved
         if target.executable != start_executable:
diff --git a/tests/test_py_info_extra.py b/tests/test_py_info_extra.py
index b7642bd..d93fb90 100644
--- a/tests/test_py_info_extra.py
+++ b/tests/test_py_info_extra.py
@@ -490,6 +490,55 @@ def test_resolve_to_system_resolved_from_exe(mocker: MockerFixture, caplog: pyte
     assert result.executable == "/some/venv/python"
 
 
+def test_from_exe_uses_supplied_environment_for_base_probe(
+    mocker: MockerFixture, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setenv("PYTHONPATH", "process-only")
+    target = copy.deepcopy(CURRENT)
+    target.executable = "venv"
+    target.system_executable = "system"
+    mapped = copy.deepcopy(CURRENT)
+    mapped.executable = mapped.system_executable = "system"
+    mapped.path = ["mapped"]
+    process_only = copy.deepcopy(mapped)
+    process_only.path = ["process-only"]
+    mocker.patch(
+        "python_discovery._cached_py_info.from_exe",
+        side_effect=lambda _cls, _cache, exe, **kwargs: {
+            "venv": target,
+            "system": mapped if kwargs["env"] == {"PYTHONPATH": "mapped"} else process_only,
+        }[exe],
+    )
+
+    info = PythonInfo.from_exe("venv", env={"PYTHONPATH": "mapped"})
+
+    assert info is not None
+    assert info.path == ["mapped"]
+
+
+def test_resolve_to_system_uses_supplied_environment_for_prefix_probe(mocker: MockerFixture) -> None:
+    target = copy.deepcopy(CURRENT)
+    target.system_executable = None
+    target.real_prefix = None
+    target.base_prefix = "/prefix"
+
+    mapped = copy.deepcopy(CURRENT)
+    mapped.path = ["mapped"]
+    mapped.system_executable = mapped.executable
+    fallback = copy.deepcopy(CURRENT)
+    fallback.path = ["process"]
+    fallback.system_executable = fallback.executable
+    mocker.patch.object(
+        PythonInfo,
+        "discover_exe",
+        side_effect=lambda _cache, **kwargs: mapped if kwargs.get("env") == {"PYTHONPATH": "mapped"} else fallback,
+    )
+
+    resolved = PythonInfo.resolve_to_system(None, target, env={"PYTHONPATH": "mapped"})
+
+    assert resolved.path == ["mapped"]
+
+
 def test_resolve_to_system_from_exe_returns_none(mocker: MockerFixture) -> None:
     target = copy.deepcopy(CURRENT)
     target.system_executable = "/some/system/python"