diff --git a/cli/tests/test_cli_web.py b/cli/tests/test_cli_web.py
index 9605c906..26990be3 100644
--- a/cli/tests/test_cli_web.py
+++ b/cli/tests/test_cli_web.py
@@ -7,6 +7,7 @@ import time
 import zipfile
 import tempfile
 import base64
+import shutil
 from io import BytesIO
 
 import pytest
@@ -185,6 +186,134 @@ class TestWeb:
             assert webhook_url == "http://127.0.0.1:1337/example"
             assert webhook_data == "1 file submitted to OnionShare"
 
+    def test_receive_mode_message_no_files(self, temp_dir, common_obj):
+        web = web_obj(temp_dir, common_obj, "receive")
+
+        data_dir = os.path.join(temp_dir, "OnionShare")
+        os.makedirs(data_dir, exist_ok=True)
+
+        web.settings.set("receive", "data_dir", data_dir)
+
+        with web.app.test_client() as c:
+            res = c.post(
+                "/upload-ajax",
+                buffered=True,
+                content_type="multipart/form-data",
+                data={"text": "you know just sending an anonymous message"},
+                headers=self._make_auth_headers(web.password),
+            )
+            content = res.get_data()
+            assert res.status_code == 200
+            assert b"Message submitted" in content
+
+        # ~/OnionShare should have a folder for the date
+        filenames = os.listdir(data_dir)
+        assert len(filenames) == 1
+        data_dir_date = os.path.join(data_dir, filenames[0])
+
+        # The date folder should have a single message txt file, no folders
+        filenames = os.listdir(data_dir_date)
+        assert len(filenames) == 1
+        assert filenames[0].endswith("-message.txt")
+
+        shutil.rmtree(data_dir)
+
+    def test_receive_mode_message_and_files(self, temp_dir, common_obj):
+        web = web_obj(temp_dir, common_obj, "receive")
+
+        data_dir = os.path.join(temp_dir, "OnionShare")
+        os.makedirs(data_dir, exist_ok=True)
+
+        web.settings.set("receive", "data_dir", data_dir)
+
+        with web.app.test_client() as c:
+            res = c.post(
+                "/upload-ajax",
+                buffered=True,
+                content_type="multipart/form-data",
+                data={
+                    "file[]": (BytesIO(b"THIS IS A TEST FILE"), "new_york.jpg"),
+                    "text": "you know just sending an anonymous message",
+                },
+                headers=self._make_auth_headers(web.password),
+            )
+            content = res.get_data()
+            assert res.status_code == 200
+            assert b"Message submitted, uploaded new_york.jpg" in content
+
+        # Date folder should have a time folder with new_york.jpg, and a text message file
+        data_dir_date = os.path.join(data_dir, os.listdir(data_dir)[0])
+        filenames = os.listdir(data_dir_date)
+        assert len(filenames) == 2
+        time_str = filenames[0][0:6]
+        assert time_str in filenames
+        assert f"{time_str}-message.txt" in filenames
+        data_dir_time = os.path.join(data_dir_date, time_str)
+        assert os.path.isdir(data_dir_time)
+        assert os.path.exists(os.path.join(data_dir_time, "new_york.jpg"))
+
+        shutil.rmtree(data_dir)
+
+    def test_receive_mode_files_no_message(self, temp_dir, common_obj):
+        web = web_obj(temp_dir, common_obj, "receive")
+
+        data_dir = os.path.join(temp_dir, "OnionShare")
+        os.makedirs(data_dir, exist_ok=True)
+
+        web.settings.set("receive", "data_dir", data_dir)
+
+        with web.app.test_client() as c:
+            res = c.post(
+                "/upload-ajax",
+                buffered=True,
+                content_type="multipart/form-data",
+                data={"file[]": (BytesIO(b"THIS IS A TEST FILE"), "new_york.jpg")},
+                headers=self._make_auth_headers(web.password),
+            )
+            content = res.get_data()
+            assert res.status_code == 200
+            assert b"Uploaded new_york.jpg" in content
+
+        # Date folder should have just a time folder with new_york.jpg
+        data_dir_date = os.path.join(data_dir, os.listdir(data_dir)[0])
+        filenames = os.listdir(data_dir_date)
+        assert len(filenames) == 1
+        time_str = filenames[0][0:6]
+        assert time_str in filenames
+        assert f"{time_str}-message.txt" not in filenames
+        data_dir_time = os.path.join(data_dir_date, time_str)
+        assert os.path.isdir(data_dir_time)
+        assert os.path.exists(os.path.join(data_dir_time, "new_york.jpg"))
+
+        shutil.rmtree(data_dir)
+
+    def test_receive_mode_no_message_no_files(self, temp_dir, common_obj):
+        web = web_obj(temp_dir, common_obj, "receive")
+
+        data_dir = os.path.join(temp_dir, "OnionShare")
+        os.makedirs(data_dir, exist_ok=True)
+
+        web.settings.set("receive", "data_dir", data_dir)
+
+        with web.app.test_client() as c:
+            res = c.post(
+                "/upload-ajax",
+                buffered=True,
+                content_type="multipart/form-data",
+                data={},
+                headers=self._make_auth_headers(web.password),
+            )
+            content = res.get_data()
+            assert res.status_code == 200
+            assert b"Nothing submitted" in content
+
+        # Date folder should be empty
+        data_dir_date = os.path.join(data_dir, os.listdir(data_dir)[0])
+        filenames = os.listdir(data_dir_date)
+        assert len(filenames) == 0
+
+        shutil.rmtree(data_dir)
+
     def test_public_mode_on(self, temp_dir, common_obj):
         web = web_obj(temp_dir, common_obj, "receive")
         web.settings.set("general", "public", True)