diff --git a/samcli/lib/init/__init__.py b/samcli/lib/init/__init__.py
index 56a948c6b2..089d81f18e 100644
--- a/samcli/lib/init/__init__.py
+++ b/samcli/lib/init/__init__.py
@@ -3,6 +3,7 @@
 """
 import itertools
 import logging
+import platform
 
 from pathlib import Path
 
@@ -11,6 +12,7 @@
 
 from samcli.local.common.runtime_template import RUNTIME_DEP_TEMPLATE_MAPPING
 from samcli.lib.utils.packagetype import ZIP
+from samcli.lib.utils import osutils
 from .exceptions import GenerateProjectFailedError, InvalidLocationError
 from .arbitrary_project import generate_non_cookiecutter_project
 
@@ -90,6 +92,12 @@ def generate_project(
     try:
         LOG.debug("Baking a new template with cookiecutter with all parameters")
         cookiecutter(**params)
+        # Fixes gradlew line ending issue caused by Windows git
+        # gradlew is a shell script which should not have CR LF line endings
+        # Putting the conversion after cookiecutter as cookiecutter processing will also change the line endings
+        # https://github.com/cookiecutter/cookiecutter/pull/1407
+        if platform.system().lower() == "windows":
+            osutils.convert_files_to_unix_line_endings(output_dir, ["gradlew"])
     except RepositoryNotFound as e:
         # cookiecutter.json is not found in the template. Let's just clone it directly without using cookiecutter
         # and call it done.
diff --git a/samcli/lib/utils/osutils.py b/samcli/lib/utils/osutils.py
index bdff5ea3b2..68b6fa02d1 100644
--- a/samcli/lib/utils/osutils.py
+++ b/samcli/lib/utils/osutils.py
@@ -8,6 +8,7 @@
 import sys
 import tempfile
 from contextlib import contextmanager
+from typing import List, Optional
 
 LOG = logging.getLogger(__name__)
 
@@ -154,3 +155,21 @@ def copytree(source, destination, ignore=None):
             copytree(new_source, new_destination, ignore=ignore)
         else:
             shutil.copy2(new_source, new_destination)
+
+
+def convert_files_to_unix_line_endings(path: str, target_files: Optional[List[str]] = None) -> None:
+    for subdirectory, _, files in os.walk(path):
+        for file in files:
+            if target_files is not None and file not in target_files:
+                continue
+
+            file_path = os.path.join(subdirectory, file)
+            convert_to_unix_line_ending(file_path)
+
+
+def convert_to_unix_line_ending(file_path: str) -> None:
+    with open(file_path, "rb") as file:
+        content = file.read()
+    content = content.replace(b"\r\n", b"\n")
+    with open(file_path, "wb") as file:
+        file.write(content)
diff --git a/tests/integration/buildcmd/test_build_cmd.py b/tests/integration/buildcmd/test_build_cmd.py
index 712698d7a1..8eab44ed32 100644
--- a/tests/integration/buildcmd/test_build_cmd.py
+++ b/tests/integration/buildcmd/test_build_cmd.py
@@ -336,8 +336,6 @@ class TestBuildCommand_Java(BuildIntegBase):
     USING_GRADLEW_PATH = os.path.join("Java", "gradlew")
     USING_GRADLE_KOTLIN_PATH = os.path.join("Java", "gradle-kotlin")
     USING_MAVEN_PATH = os.path.join("Java", "maven")
-    WINDOWS_LINE_ENDING = b"\r\n"
-    UNIX_LINE_ENDING = b"\n"
 
     @parameterized.expand(
         [
@@ -402,7 +400,7 @@ def _test_with_building_java(self, runtime, code_path, expected_files, use_conta
         cmdlist = self.get_command_list(use_container=use_container, parameter_overrides=overrides)
         cmdlist += ["--skip-pull-image"]
         if code_path == self.USING_GRADLEW_PATH and use_container and IS_WINDOWS:
-            self._change_to_unix_line_ending(os.path.join(self.test_data_path, self.USING_GRADLEW_PATH, "gradlew"))
+            osutils.convert_to_unix_line_ending(os.path.join(self.test_data_path, self.USING_GRADLEW_PATH, "gradlew"))
 
         LOG.info("Running Command: {}".format(cmdlist))
         run_command(cmdlist, cwd=self.working_dir)
@@ -465,15 +463,6 @@ def _verify_built_artifact(self, build_dir, function_logical_id, expected_files,
         lib_dir_contents = set(os.listdir(str(resource_artifact_dir.joinpath("lib"))))
         self.assertEqual(lib_dir_contents, expected_modules)
 
-    def _change_to_unix_line_ending(self, path):
-        with open(os.path.abspath(path), "rb") as open_file:
-            content = open_file.read()
-
-        content = content.replace(self.WINDOWS_LINE_ENDING, self.UNIX_LINE_ENDING)
-
-        with open(os.path.abspath(path), "wb") as open_file:
-            open_file.write(content)
-
 
 @skipIf(
     ((IS_WINDOWS and RUNNING_ON_CI) and not CI_OVERRIDE),
diff --git a/tests/unit/lib/utils/test_osutils.py b/tests/unit/lib/utils/test_osutils.py
index d7633509b0..fbcdb10a81 100644
--- a/tests/unit/lib/utils/test_osutils.py
+++ b/tests/unit/lib/utils/test_osutils.py
@@ -61,3 +61,19 @@ def test_must_return_sys_stdout(self):
             expected_stdout = sys.stdout.buffer
 
         self.assertEqual(expected_stdout, osutils.stdout())
+
+
+class Test_convert_files_to_unix_line_endings:
+    @patch("os.walk")
+    @patch("builtins.open")
+    def test_must_return_sys_stdout(self, patched_open, os_walk):
+        target_file = "target_file"
+        os_walk.return_value = [
+            ("a", "_", ("file_a_1", "file_a_2", target_file)),
+            ("b", "_", ("file_b_1", target_file)),
+        ]
+        osutils.convert_files_to_unix_line_endings("path", [target_file])
+        patched_open.assert_any_call(os.path.join("a", target_file), "rb")
+        patched_open.assert_any_call(os.path.join("b", target_file), "rb")
+        patched_open.assert_any_call(os.path.join("a", target_file), "wb")
+        patched_open.assert_any_call(os.path.join("b", target_file), "wb")