diff --git a/py/private/venv/venv.bzl b/py/private/venv/venv.bzl
index 8c9f2a14..8b898c45 100644
--- a/py/private/venv/venv.bzl
+++ b/py/private/venv/venv.bzl
@@ -92,8 +92,7 @@ def _make_venv(ctx, name = None, main = None, strip_pth_workspace_root = None):
         content = pth_lines,
     )
 
-    venv_sibling = _get_attr(ctx.file, "main", main)
-    venv_directory = ctx.actions.declare_directory("%s.source" % name, sibling = venv_sibling)
+    venv_directory = ctx.actions.declare_directory("%s.source" % name)
 
     common_substitutions = {
         "{{BASH_BIN}}": bash_bin,
diff --git a/py/tests/external-deps/BUILD.bazel b/py/tests/external-deps/BUILD.bazel
index 54afebb9..3ecf6f54 100644
--- a/py/tests/external-deps/BUILD.bazel
+++ b/py/tests/external-deps/BUILD.bazel
@@ -1,6 +1,7 @@
 load("//py:defs.bzl", "py_binary", "py_library")
 load("@python_toolchain//:defs.bzl", "host_platform")
 load("@aspect_bazel_lib//lib:write_source_files.bzl", "write_source_files")
+load("//py/tests/external-deps/custom-macro:macro.bzl", "click_cli_binary")
 
 py_library(
     name = "lib",
@@ -33,7 +34,7 @@ genrule(
 
 py_binary(
     name = "click",
-    srcs = ["click.py"],
+    srcs = ["//py/tests/external-deps/custom-macro:__main__.py"],
     deps = [
         # Referencing the external py_library rule generated by rules_python
         "@pypi_click//:pkg",
@@ -47,10 +48,22 @@ genrule(
     tools = ["click"],
 )
 
+click_cli_binary(
+    name = "click_binary",
+)
+
+genrule(
+    name = "run_click_cli_binary",
+    outs = ["click_cli_binary_out"],
+    cmd = "$(execpath click_binary) --count 628 > $@",
+    tools = ["click_binary"],
+)
+
 write_source_files(
     name = "test",
     files = {
         "expected_pathing": "pathing_out",
         "expected_click": "click_out",
+        "expected_click_cli_binary": "click_cli_binary_out",
     },
 )
diff --git a/py/tests/external-deps/custom-macro/BUILD.bazel b/py/tests/external-deps/custom-macro/BUILD.bazel
new file mode 100644
index 00000000..f35309b0
--- /dev/null
+++ b/py/tests/external-deps/custom-macro/BUILD.bazel
@@ -0,0 +1 @@
+exports_files(["__main__.py"])
diff --git a/py/tests/external-deps/click.py b/py/tests/external-deps/custom-macro/__main__.py
similarity index 100%
rename from py/tests/external-deps/click.py
rename to py/tests/external-deps/custom-macro/__main__.py
diff --git a/py/tests/external-deps/custom-macro/macro.bzl b/py/tests/external-deps/custom-macro/macro.bzl
new file mode 100644
index 00000000..9ed82314
--- /dev/null
+++ b/py/tests/external-deps/custom-macro/macro.bzl
@@ -0,0 +1,17 @@
+load("//py:defs.bzl", "py_binary", "py_library")
+
+def click_cli_binary(name, deps = [], **kwargs):
+    py_library(
+        name = name + "_lib",
+        srcs = ["//py/tests/external-deps/custom-macro:__main__.py"],
+    )
+
+    py_binary(
+        name = name,
+        main = "//py/tests/external-deps/custom-macro:__main__.py",
+        deps = deps + [
+            name + "_lib",
+            "@pypi_click//:pkg",
+        ],
+        **kwargs
+    )
diff --git a/py/tests/external-deps/expected_click_cli_binary b/py/tests/external-deps/expected_click_cli_binary
new file mode 100644
index 00000000..cc973039
--- /dev/null
+++ b/py/tests/external-deps/expected_click_cli_binary
@@ -0,0 +1 @@
+Count = 628
diff --git a/py/tests/external-deps/sibling-package/BUILD.bazel b/py/tests/external-deps/sibling-package/BUILD.bazel
new file mode 100644
index 00000000..5ceda7b8
--- /dev/null
+++ b/py/tests/external-deps/sibling-package/BUILD.bazel
@@ -0,0 +1,20 @@
+load("//py/tests/external-deps/custom-macro:macro.bzl", "click_cli_binary")
+load("@aspect_bazel_lib//lib:write_source_files.bzl", "write_source_files")
+
+click_cli_binary(
+    name = "click_sibling_binary",
+)
+
+genrule(
+    name = "run_click_cli_binary",
+    outs = ["click_sibling_cli_binary_out"],
+    cmd = "$(execpath click_sibling_binary) --count 628 > $@",
+    tools = ["click_sibling_binary"],
+)
+
+write_source_files(
+    name = "test",
+    files = {
+        "expected_click_sibling_cli_binary": "click_sibling_cli_binary_out",
+    },
+)
diff --git a/py/tests/external-deps/sibling-package/expected_click_sibling_cli_binary b/py/tests/external-deps/sibling-package/expected_click_sibling_cli_binary
new file mode 100755
index 00000000..cc973039
--- /dev/null
+++ b/py/tests/external-deps/sibling-package/expected_click_sibling_cli_binary
@@ -0,0 +1 @@
+Count = 628
diff --git a/py/tests/external-deps/sibling-package/expected_click_sibling_cli_binary_out b/py/tests/external-deps/sibling-package/expected_click_sibling_cli_binary_out
new file mode 100644
index 00000000..cc973039
--- /dev/null
+++ b/py/tests/external-deps/sibling-package/expected_click_sibling_cli_binary_out
@@ -0,0 +1 @@
+Count = 628