diff --git a/sh.py b/sh.py
index 04fe4ad4..cab0cf9c 100644
--- a/sh.py
+++ b/sh.py
@@ -1425,7 +1425,10 @@ def __call__(self, *args, **kwargs):
             pcall_args.pop("with", None)
 
             call_args.update(pcall_args)
-            cmd.extend(prepend.cmd)
+            # we do not prepend commands used as a 'with' context as they will
+            # be prepended to any nested commands
+            if not kwargs.get("_with", False):
+                cmd.extend(prepend.cmd)
 
         cmd.append(self._path)
 
diff --git a/tests/test.py b/tests/test.py
index 8ffac583..babaff92 100644
--- a/tests/test.py
+++ b/tests/test.py
@@ -1101,6 +1101,13 @@ def test_with_context_args(self):
             out = whoami()
         self.assertEqual(out.strip(), "")
 
+    def test_with_context_nested(self):
+        echo_path = sh.echo._path
+        with sh.echo.bake("test1", _with=True):
+            with sh.echo.bake("test2", _with=True):
+                out = sh.echo("test3")
+        self.assertEqual(out.strip(), f"test1 {echo_path} test2 {echo_path} test3")
+
     def test_binary_input(self):
         py = create_tmp_test(
             """