diff --git a/tests/venv_site_packages_libs/BUILD.bazel b/tests/venv_site_packages_libs/BUILD.bazel
index 2ce4ad9d22..2eb9678838 100644
--- a/tests/venv_site_packages_libs/BUILD.bazel
+++ b/tests/venv_site_packages_libs/BUILD.bazel
@@ -28,6 +28,7 @@ py_reconfig_test(
     venvs_site_packages = "yes",
     deps = [
         ":closer_lib",
+        "//tests/venv_site_packages_libs/nested_with_pth",
         "//tests/venv_site_packages_libs/nspkg_alpha",
         "//tests/venv_site_packages_libs/nspkg_beta",
         "//tests/venv_site_packages_libs/pkgutil_top",
diff --git a/tests/venv_site_packages_libs/bin.py b/tests/venv_site_packages_libs/bin.py
index 772925f00e..c075f4fc65 100644
--- a/tests/venv_site_packages_libs/bin.py
+++ b/tests/venv_site_packages_libs/bin.py
@@ -40,6 +40,8 @@ def test_imported_from_venv(self):
         self.assert_imported_from_venv("nspkg.subnspkg.delta")
         self.assert_imported_from_venv("single_file")
         self.assert_imported_from_venv("simple")
+        m = self.assert_imported_from_venv("nested_with_pth")
+        self.assertEqual(m.WHOAMI, "nested_with_pth")
 
     def test_data_is_included(self):
         self.assert_imported_from_venv("simple")
diff --git a/tests/venv_site_packages_libs/nested_with_pth/BUILD.bazel b/tests/venv_site_packages_libs/nested_with_pth/BUILD.bazel
new file mode 100644
index 0000000000..68c16cfde9
--- /dev/null
+++ b/tests/venv_site_packages_libs/nested_with_pth/BUILD.bazel
@@ -0,0 +1,11 @@
+load("//python:py_library.bzl", "py_library")
+
+package(default_visibility = ["//visibility:public"])
+
+py_library(
+    name = "nested_with_pth",
+    srcs = glob(["site-packages/**/*.py"]),
+    data = glob(["site-packages/*.pth"]),
+    experimental_venvs_site_packages = "//python/config_settings:venvs_site_packages",
+    imports = [package_name() + "/site-packages"],
+)
diff --git a/tests/venv_site_packages_libs/nested_with_pth/site-packages/nested.pth b/tests/venv_site_packages_libs/nested_with_pth/site-packages/nested.pth
new file mode 100644
index 0000000000..924e0dccc8
--- /dev/null
+++ b/tests/venv_site_packages_libs/nested_with_pth/site-packages/nested.pth
@@ -0,0 +1 @@
+nested_sdk
diff --git a/tests/venv_site_packages_libs/nested_with_pth/site-packages/nested_sdk/nested_with_pth/__init__.py b/tests/venv_site_packages_libs/nested_with_pth/site-packages/nested_sdk/nested_with_pth/__init__.py
new file mode 100644
index 0000000000..adde64d3ef
--- /dev/null
+++ b/tests/venv_site_packages_libs/nested_with_pth/site-packages/nested_sdk/nested_with_pth/__init__.py
@@ -0,0 +1 @@
+WHOAMI = "nested_with_pth"