diff --git a/optional_requirements.txt b/optional_requirements.txt
index d4e27c4..38e5c0c 100644
--- a/optional_requirements.txt
+++ b/optional_requirements.txt
@@ -1,3 +1,5 @@
 # SPDX-FileCopyrightText: 2022 Alec Delaney, for Adafruit Industries
 #
 # SPDX-License-Identifier: Unlicense
+
+requests
diff --git a/tests/files/green_red.png b/tests/files/green_red.png
new file mode 100644
index 0000000..7d8ddb3
Binary files /dev/null and b/tests/files/green_red.png differ
diff --git a/tests/files/green_red.png.license b/tests/files/green_red.png.license
new file mode 100644
index 0000000..d41b03e
--- /dev/null
+++ b/tests/files/green_red.png.license
@@ -0,0 +1,2 @@
+# SPDX-FileCopyrightText: 2024 Justin Myers
+# SPDX-License-Identifier: Unlicense
diff --git a/tests/files/red_green.png b/tests/files/red_green.png
new file mode 100644
index 0000000..6b4fc30
Binary files /dev/null and b/tests/files/red_green.png differ
diff --git a/tests/files/red_green.png.license b/tests/files/red_green.png.license
new file mode 100644
index 0000000..d41b03e
--- /dev/null
+++ b/tests/files/red_green.png.license
@@ -0,0 +1,2 @@
+# SPDX-FileCopyrightText: 2024 Justin Myers
+# SPDX-License-Identifier: Unlicense
diff --git a/tests/files_test.py b/tests/files_test.py
new file mode 100644
index 0000000..8299b1b
--- /dev/null
+++ b/tests/files_test.py
@@ -0,0 +1,214 @@
+# SPDX-FileCopyrightText: 2024 Justin Myers
+#
+# SPDX-License-Identifier: Unlicense
+
+""" Post Files Tests """
+# pylint: disable=line-too-long
+
+import re
+from unittest import mock
+
+import mocket
+import pytest
+import requests as python_requests
+
+
+@pytest.fixture
+def log_stream():
+    return []
+
+
+@pytest.fixture
+def post_url():
+    return "https://httpbin.org/post"
+
+
+@pytest.fixture
+def request_logging(log_stream):
+    """Reset the ConnectionManager, since it's a singlton and will hold data"""
+    import http.client  # pylint: disable=import-outside-toplevel
+
+    def httpclient_log(*args):
+        log_stream.append(args)
+
+    http.client.print = httpclient_log
+    http.client.HTTPConnection.debuglevel = 1
+
+
+def get_actual_request_data(log_stream):
+    boundary_pattern = r"(?<=boundary=)(.\w*)"
+    content_length_pattern = r"(?<=Content-Length: )(.\d*)"
+
+    boundary = ""
+    actual_request_post = ""
+    content_length = ""
+    for log in log_stream:
+        for log_arg in log:
+            boundary_search = re.findall(boundary_pattern, log_arg)
+            content_length_search = re.findall(content_length_pattern, log_arg)
+            if boundary_search:
+                boundary = boundary_search[0]
+            if content_length_search:
+                content_length = content_length_search[0]
+            if "Content-Disposition" in log_arg:
+                # this will look like:
+                #  b\'{content}\'
+                # and escaped characters look like:
+                #  \\r
+                post_data = log_arg[2:-1]
+                post_bytes = post_data.encode("utf-8")
+                post_unescaped = post_bytes.decode("unicode_escape")
+                actual_request_post = post_unescaped.encode("latin1")
+
+    return boundary, content_length, actual_request_post
+
+
+def test_post_files_text(  # pylint: disable=unused-argument
+    sock, requests, log_stream, post_url, request_logging
+):
+    file_data = {
+        "key_4": (None, "Value 5"),
+    }
+
+    python_requests.post(post_url, files=file_data, timeout=30)
+    boundary, content_length, actual_request_post = get_actual_request_data(log_stream)
+
+    requests._build_boundary_string = mock.Mock(return_value=boundary)
+    requests.post("http://" + mocket.MOCK_HOST_1 + "/post", files=file_data)
+
+    sock.connect.assert_called_once_with((mocket.MOCK_POOL_IP, 80))
+    sock.send.assert_has_calls(
+        [
+            mock.call(b"Content-Type"),
+            mock.call(b": "),
+            mock.call(f"multipart/form-data; boundary={boundary}".encode()),
+            mock.call(b"\r\n"),
+        ]
+    )
+    sock.send.assert_has_calls(
+        [
+            mock.call(b"Content-Length"),
+            mock.call(b": "),
+            mock.call(content_length.encode()),
+            mock.call(b"\r\n"),
+        ]
+    )
+
+    sent = b"".join(sock.sent_data)
+    assert sent.endswith(actual_request_post)
+
+
+def test_post_files_file(  # pylint: disable=unused-argument
+    sock, requests, log_stream, post_url, request_logging
+):
+    with open("tests/files/red_green.png", "rb") as file_1:
+        file_data = {
+            "file_1": (
+                "red_green.png",
+                file_1,
+                "image/png",
+                {
+                    "Key_1": "Value 1",
+                    "Key_2": "Value 2",
+                    "Key_3": "Value 3",
+                },
+            ),
+        }
+
+        python_requests.post(post_url, files=file_data, timeout=30)
+        boundary, content_length, actual_request_post = get_actual_request_data(
+            log_stream
+        )
+
+        requests._build_boundary_string = mock.Mock(return_value=boundary)
+        requests.post("http://" + mocket.MOCK_HOST_1 + "/post", files=file_data)
+
+    sock.connect.assert_called_once_with((mocket.MOCK_POOL_IP, 80))
+    sock.send.assert_has_calls(
+        [
+            mock.call(b"Content-Type"),
+            mock.call(b": "),
+            mock.call(f"multipart/form-data; boundary={boundary}".encode()),
+            mock.call(b"\r\n"),
+        ]
+    )
+    sock.send.assert_has_calls(
+        [
+            mock.call(b"Content-Length"),
+            mock.call(b": "),
+            mock.call(content_length.encode()),
+            mock.call(b"\r\n"),
+        ]
+    )
+    sent = b"".join(sock.sent_data)
+    assert sent.endswith(actual_request_post)
+
+
+def test_post_files_complex(  # pylint: disable=unused-argument
+    sock, requests, log_stream, post_url, request_logging
+):
+    with open("tests/files/red_green.png", "rb") as file_1, open(
+        "tests/files/green_red.png", "rb"
+    ) as file_2:
+        file_data = {
+            "file_1": (
+                "red_green.png",
+                file_1,
+                "image/png",
+                {
+                    "Key_1": "Value 1",
+                    "Key_2": "Value 2",
+                    "Key_3": "Value 3",
+                },
+            ),
+            "key_4": (None, "Value 5"),
+            "file_2": (
+                "green_red.png",
+                file_2,
+                "image/png",
+            ),
+            "key_6": (None, "Value 6"),
+        }
+
+        python_requests.post(post_url, files=file_data, timeout=30)
+        boundary, content_length, actual_request_post = get_actual_request_data(
+            log_stream
+        )
+
+        requests._build_boundary_string = mock.Mock(return_value=boundary)
+        requests.post("http://" + mocket.MOCK_HOST_1 + "/post", files=file_data)
+
+    sock.connect.assert_called_once_with((mocket.MOCK_POOL_IP, 80))
+    sock.send.assert_has_calls(
+        [
+            mock.call(b"Content-Type"),
+            mock.call(b": "),
+            mock.call(f"multipart/form-data; boundary={boundary}".encode()),
+            mock.call(b"\r\n"),
+        ]
+    )
+    sock.send.assert_has_calls(
+        [
+            mock.call(b"Content-Length"),
+            mock.call(b": "),
+            mock.call(content_length.encode()),
+            mock.call(b"\r\n"),
+        ]
+    )
+    sent = b"".join(sock.sent_data)
+    assert sent.endswith(actual_request_post)
+
+
+def test_post_files_not_binary(requests):
+    with open("tests/files/red_green.png", "r") as file_1:
+        file_data = {
+            "file_1": (
+                "red_green.png",
+                file_1,
+                "image/png",
+            ),
+        }
+
+        with pytest.raises(AttributeError) as context:
+            requests.post("http://" + mocket.MOCK_HOST_1 + "/post", files=file_data)
+        assert "Files must be opened in binary mode" in str(context)