diff --git a/examples/wheel/wheel_test.py b/examples/wheel/wheel_test.py
index f326af20c6..8200e54cfd 100644
--- a/examples/wheel/wheel_test.py
+++ b/examples/wheel/wheel_test.py
@@ -238,6 +238,14 @@ def test_custom_package_root_wheel(self):
                 ],
             )
 
+            record_contents = zf.read(
+                "examples_custom_package_root-0.0.1.dist-info/RECORD"
+            ).decode("utf-8")
+
+            # Ensure RECORD files do not have leading forward slashes
+            for line in record_contents.splitlines():
+                self.assertFalse(line.startswith("/"))
+
     def test_custom_package_root_multi_prefix_wheel(self):
         filename = os.path.join(
             os.environ["TEST_SRCDIR"],
@@ -261,6 +269,14 @@ def test_custom_package_root_multi_prefix_wheel(self):
                 ],
             )
 
+            record_contents = zf.read(
+                "example_custom_package_root_multi_prefix-0.0.1.dist-info/RECORD"
+            ).decode("utf-8")
+
+            # Ensure RECORD files do not have leading forward slashes
+            for line in record_contents.splitlines():
+                self.assertFalse(line.startswith("/"))
+
     def test_custom_package_root_multi_prefix_reverse_order_wheel(self):
         filename = os.path.join(
             os.environ["TEST_SRCDIR"],
@@ -284,6 +300,14 @@ def test_custom_package_root_multi_prefix_reverse_order_wheel(self):
                 ],
             )
 
+            record_contents = zf.read(
+                "example_custom_package_root_multi_prefix_reverse_order-0.0.1.dist-info/RECORD"
+            ).decode("utf-8")
+
+            # Ensure RECORD files do not have leading forward slashes
+            for line in record_contents.splitlines():
+                self.assertFalse(line.startswith("/"))
+
     def test_python_requires_wheel(self):
         filename = os.path.join(
             os.environ["TEST_SRCDIR"],
diff --git a/tools/wheelmaker.py b/tools/wheelmaker.py
index b5ad346d70..fb8e37b5a9 100644
--- a/tools/wheelmaker.py
+++ b/tools/wheelmaker.py
@@ -214,7 +214,7 @@ def add_recordfile(self):
         contents = b""
         for filename, digest, size in entries:
             if sys.version_info[0] > 2 and isinstance(filename, str):
-                filename = filename.encode("utf-8", "surrogateescape")
+                filename = filename.lstrip("/").encode("utf-8", "surrogateescape")
             contents += b"%s,%s,%s\n" % (filename, digest, size)
         self.add_string(record_path, contents)