diff --git a/python/private/py_executable.bzl b/python/private/py_executable.bzl
index d5c0fa5388..669951e172 100644
--- a/python/private/py_executable.bzl
+++ b/python/private/py_executable.bzl
@@ -356,7 +356,7 @@ def _create_executable(
             [stage2_bootstrap] + (
                 venv.files_without_interpreter if venv else []
             ),
-        )
+        ).merge(venv.lib_runfiles)
         zip_main = _create_zip_main(
             ctx,
             stage2_bootstrap = stage2_bootstrap,
@@ -606,7 +606,7 @@ def _create_venv(ctx, output_prefix, imports, runtime_details):
     }
     venv_app_files = create_venv_app_files(ctx, ctx.attr.deps, venv_dir_map)
 
-    files_without_interpreter = [pth, site_init] + venv_app_files
+    files_without_interpreter = [pth, site_init] + venv_app_files.venv_files
     if pyvenv_cfg:
         files_without_interpreter.append(pyvenv_cfg)
 
@@ -629,6 +629,11 @@ def _create_venv(ctx, output_prefix, imports, runtime_details):
                 venv,
             ),
         ),
+        # venv files for user library dependencies (files that are specific
+        # to the executable bootstrap and python runtime aren't here).
+        lib_runfiles = ctx.runfiles(
+            symlinks = venv_app_files.runfiles_symlinks,
+        ),
     )
 
 def _map_each_identity(v):
diff --git a/python/private/venv_runfiles.bzl b/python/private/venv_runfiles.bzl
index 05dc296e15..eeedda4555 100644
--- a/python/private/venv_runfiles.bzl
+++ b/python/private/venv_runfiles.bzl
@@ -30,7 +30,12 @@ def create_venv_app_files(ctx, deps, venv_dir_map):
             paths within the current ctx's venv (e.g. `_foo.venv/bin`).
 
     Returns:
-        {type}`list[File]` of the files that were created.
+        {type}`struct` with the following attributes:
+        * {type}`list[File]` `venv_files` additional files created for
+          the venv.
+        * {type}`dict[str, File]` `runfiles_symlinks` map intended for
+          the `runfiles.symlinks` argument. A map of main-repo
+          relative paths to File.
     """
 
     # maps venv-relative path to the runfiles path it should point to
@@ -44,16 +49,16 @@ def create_venv_app_files(ctx, deps, venv_dir_map):
 
     link_map = build_link_map(ctx, entries)
     venv_files = []
+    runfiles_symlinks = {}
+
     for kind, kind_map in link_map.items():
         base = venv_dir_map[kind]
         for venv_path, link_to in kind_map.items():
             bin_venv_path = paths.join(base, venv_path)
             if is_file(link_to):
-                if link_to.is_directory:
-                    venv_link = ctx.actions.declare_directory(bin_venv_path)
-                else:
-                    venv_link = ctx.actions.declare_file(bin_venv_path)
-                ctx.actions.symlink(output = venv_link, target_file = link_to)
+                symlink_from = "{}/{}".format(ctx.label.package, bin_venv_path)
+                runfiles_symlinks[symlink_from] = link_to
+
             else:
                 venv_link = ctx.actions.declare_symlink(bin_venv_path)
                 venv_link_rf_path = runfiles_root_path(ctx, venv_link.short_path)
@@ -64,9 +69,12 @@ def create_venv_app_files(ctx, deps, venv_dir_map):
                     to = link_to,
                 )
                 ctx.actions.symlink(output = venv_link, target_path = rel_path)
-            venv_files.append(venv_link)
+                venv_files.append(venv_link)
 
-    return venv_files
+    return struct(
+        venv_files = venv_files,
+        runfiles_symlinks = runfiles_symlinks,
+    )
 
 # Visible for testing
 def build_link_map(ctx, entries):