diff --git a/CHANGELOG.md b/CHANGELOG.md
index e0a447c8..7967e69f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ### Changed
 
+- Changed `push_to_s3` deployment step function to write paths `as_posix()` to allow support for deploying from windows [#314](https://github.com/PrefectHQ/prefect-aws/pull/314)
+
 ### Deprecated
 
 ### Removed
diff --git a/prefect_aws/deployments/steps.py b/prefect_aws/deployments/steps.py
index 805b4648..5609a044 100644
--- a/prefect_aws/deployments/steps.py
+++ b/prefect_aws/deployments/steps.py
@@ -117,7 +117,9 @@ def push_to_s3(
             continue
         elif not local_file_path.is_dir():
             remote_file_path = Path(folder) / local_file_path.relative_to(local_path)
-            client.upload_file(str(local_file_path), bucket, str(remote_file_path))
+            client.upload_file(
+                str(local_file_path), bucket, str(remote_file_path.as_posix())
+            )
 
     return {
         "bucket": bucket,
diff --git a/tests/deploments/test_steps.py b/tests/deploments/test_steps.py
index 5e2d2efd..a2312d18 100644
--- a/tests/deploments/test_steps.py
+++ b/tests/deploments/test_steps.py
@@ -1,4 +1,5 @@
 import os
+import sys
 from pathlib import Path, PurePath, PurePosixPath
 
 import boto3
@@ -40,6 +41,24 @@ def tmp_files(tmp_path: Path):
     return tmp_path
 
 
+@pytest.fixture
+def tmp_files_win(tmp_path: Path):
+    files = [
+        "testfile1.txt",
+        "testfile2.txt",
+        "testfile3.txt",
+        r"testdir1\testfile4.txt",
+        r"testdir2\testfile5.txt",
+    ]
+
+    for file in files:
+        filepath = tmp_path / file
+        filepath.parent.mkdir(parents=True, exist_ok=True)
+        filepath.write_text("Sample text")
+
+    return tmp_path
+
+
 @pytest.fixture
 def mock_aws_credentials(monkeypatch):
     # Set mock environment variables for AWS credentials
@@ -77,6 +96,29 @@ def test_push_to_s3(s3_setup, tmp_files, mock_aws_credentials):
     assert set(object_keys) == set(expected_keys)
 
 
+@pytest.mark.skipif(sys.platform != "win32", reason="requires Windows")
+def test_push_to_s3_as_posix(s3_setup, tmp_files_win, mock_aws_credentials):
+    s3, bucket_name = s3_setup
+    folder = "my-project"
+
+    os.chdir(tmp_files_win)
+
+    push_to_s3(bucket_name, folder)
+
+    s3_objects = s3.list_objects_v2(Bucket=bucket_name)
+    object_keys = [item["Key"] for item in s3_objects["Contents"]]
+
+    expected_keys = [
+        f"{folder}/testfile1.txt",
+        f"{folder}/testfile2.txt",
+        f"{folder}/testfile3.txt",
+        f"{folder}/testdir1/testfile4.txt",
+        f"{folder}/testdir2/testfile5.txt",
+    ]
+
+    assert set(object_keys) == set(expected_keys)
+
+
 def test_pull_from_s3(s3_setup, tmp_path, mock_aws_credentials):
     s3, bucket_name = s3_setup
     folder = "my-project"