diff --git a/tests/test_upload_webdav_comprehensive.py b/tests/test_upload_webdav_comprehensive.py
new file mode 100644
index 00000000..80646c6e
--- /dev/null
+++ b/tests/test_upload_webdav_comprehensive.py
@@ -0,0 +1,508 @@
+"""Comprehensive tests for upload_to_webdav task."""
+import os
+import pytest
+from unittest.mock import patch, Mock, MagicMock
+from requests.exceptions import ConnectionError, Timeout, RequestException
+
+from app.tasks.upload_to_webdav import upload_to_webdav
+
+
+@pytest.mark.unit
+class TestUploadToWebDAV:
+    """Comprehensive tests for WebDAV upload task."""
+
+    def test_upload_success_with_file_id(self, sample_text_file):
+        """Test successful upload with file_id parameter."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress") as mock_log:
+            
+            # Setup settings
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            # Setup mock response - 201 Created
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            # Execute upload
+            result = upload_to_webdav.apply(args=[sample_text_file], kwargs={"file_id": 100}).get()
+            
+            # Verify result
+            assert result["status"] == "Completed"
+            assert result["file"] == sample_text_file
+            assert "url" in result
+            assert "webdav.example.com" in result["url"]
+            
+            # Verify requests.put was called correctly
+            assert mock_put.called
+            call_args = mock_put.call_args
+            assert call_args[1]["auth"] == ("test_user", "test_pass")
+            assert call_args[1]["verify"] is True
+            assert call_args[1]["timeout"] == 30
+            
+            # Verify logging was called with file_id
+            assert mock_log.called
+            log_calls_with_file_id = [
+                call for call in mock_log.call_args_list 
+                if call[1].get("file_id") == 100
+            ]
+            assert len(log_calls_with_file_id) > 0
+
+    def test_upload_success_without_file_id(self, sample_text_file):
+        """Test successful upload without file_id parameter."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = ""
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 200  # 200 OK is also valid
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            assert result["status"] == "Completed"
+            assert result["file"] == sample_text_file
+
+    def test_upload_success_status_204(self, sample_text_file):
+        """Test successful upload with 204 No Content status."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = None
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 204  # 204 No Content
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            assert result["status"] == "Completed"
+
+    def test_missing_webdav_url(self, sample_text_file):
+        """Test that missing WebDAV URL raises ValueError."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = None
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            
+            with pytest.raises(ValueError, match="WebDAV URL is not configured"):
+                upload_to_webdav.apply(args=[sample_text_file]).get()
+
+    def test_file_not_found(self):
+        """Test that missing file raises FileNotFoundError."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            
+            with pytest.raises(FileNotFoundError, match="File not found"):
+                upload_to_webdav.apply(args=["/nonexistent/file.pdf"]).get()
+
+    def test_http_error_response(self, sample_text_file):
+        """Test handling of HTTP error responses (4xx, 5xx)."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            # Simulate 401 Unauthorized
+            mock_response = Mock()
+            mock_response.status_code = 401
+            mock_response.text = "Unauthorized"
+            mock_put.return_value = mock_response
+            
+            with pytest.raises(Exception, match="Failed to upload.*401"):
+                upload_to_webdav.apply(args=[sample_text_file]).get()
+
+    def test_http_404_not_found(self, sample_text_file):
+        """Test handling of 404 Not Found response."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "nonexistent"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 404
+            mock_response.text = "Not Found"
+            mock_put.return_value = mock_response
+            
+            with pytest.raises(Exception, match="Failed to upload.*404"):
+                upload_to_webdav.apply(args=[sample_text_file]).get()
+
+    def test_http_500_server_error(self, sample_text_file):
+        """Test handling of 500 Internal Server Error."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 500
+            mock_response.text = "Internal Server Error"
+            mock_put.return_value = mock_response
+            
+            with pytest.raises(Exception, match="Failed to upload.*500"):
+                upload_to_webdav.apply(args=[sample_text_file]).get()
+
+    def test_connection_error(self, sample_text_file):
+        """Test handling of connection errors."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            # Simulate connection error
+            mock_put.side_effect = ConnectionError("Connection refused")
+            
+            with pytest.raises(Exception, match="Error uploading.*Connection refused"):
+                upload_to_webdav.apply(args=[sample_text_file]).get()
+
+    def test_timeout_error(self, sample_text_file):
+        """Test handling of timeout errors."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            # Simulate timeout
+            mock_put.side_effect = Timeout("Request timed out")
+            
+            with pytest.raises(Exception, match="Error uploading.*timed out"):
+                upload_to_webdav.apply(args=[sample_text_file]).get()
+
+    def test_url_construction_with_trailing_slash(self, sample_text_file):
+        """Test URL construction when base URL has trailing slash."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify URL construction
+            called_url = mock_put.call_args[0][0]
+            assert called_url.startswith("https://webdav.example.com/")
+            assert "uploads" in called_url
+            assert os.path.basename(sample_text_file) in called_url
+
+    def test_url_construction_without_trailing_slash(self, sample_text_file):
+        """Test URL construction when base URL has no trailing slash."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "documents"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify URL construction
+            called_url = mock_put.call_args[0][0]
+            assert "webdav.example.com" in called_url
+            assert "documents" in called_url
+
+    def test_folder_path_with_leading_slash(self, sample_text_file):
+        """Test folder path normalization when it starts with /."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "/uploads/documents"  # Leading slash
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify the leading slash was removed in URL construction
+            called_url = mock_put.call_args[0][0]
+            # Should not have double slashes like //uploads
+            assert "//" not in called_url.replace("https://", "")
+
+    def test_empty_folder_path(self, sample_text_file):
+        """Test upload with empty folder path (root directory)."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = ""  # Empty folder
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            assert result["status"] == "Completed"
+
+    def test_ssl_verification_enabled(self, sample_text_file):
+        """Test that SSL verification is enabled when configured."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify SSL verification was enabled
+            call_kwargs = mock_put.call_args[1]
+            assert call_kwargs["verify"] is True
+
+    def test_ssl_verification_disabled(self, sample_text_file):
+        """Test that SSL verification can be disabled."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = False
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify SSL verification was disabled
+            call_kwargs = mock_put.call_args[1]
+            assert call_kwargs["verify"] is False
+
+    def test_authentication_credentials(self, sample_text_file):
+        """Test that authentication credentials are properly passed."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "custom_user"
+            mock_settings.webdav_password = "custom_password123"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify correct credentials were used
+            call_kwargs = mock_put.call_args[1]
+            assert call_kwargs["auth"] == ("custom_user", "custom_password123")
+
+    def test_logging_on_success(self, sample_text_file):
+        """Test that progress is logged on successful upload."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress") as mock_log:
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            upload_to_webdav.apply(args=[sample_text_file], kwargs={"file_id": 42}).get()
+            
+            # Verify logging calls
+            assert mock_log.call_count >= 2  # At least in_progress and success
+            
+            # Check for success log
+            success_calls = [
+                call for call in mock_log.call_args_list
+                if call[0][2] == "success"
+            ]
+            assert len(success_calls) >= 1
+
+    def test_logging_on_failure(self, sample_text_file):
+        """Test that progress is logged on failed upload."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress") as mock_log:
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 403
+            mock_response.text = "Forbidden"
+            mock_put.return_value = mock_response
+            
+            with pytest.raises(Exception):
+                upload_to_webdav.apply(args=[sample_text_file], kwargs={"file_id": 42}).get()
+            
+            # Check for failure log
+            failure_calls = [
+                call for call in mock_log.call_args_list
+                if call[0][2] == "failure"
+            ]
+            assert len(failure_calls) >= 1
+
+    def test_file_content_uploaded(self, sample_text_file):
+        """Test that file content is actually read and uploaded."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Verify data was passed to PUT request
+            call_kwargs = mock_put.call_args[1]
+            assert "data" in call_kwargs
+            # Data should be a file-like object from open()
+            assert call_kwargs["data"] is not None
+
+    def test_return_value_structure(self, sample_text_file):
+        """Test that return value has correct structure."""
+        with patch("app.tasks.upload_to_webdav.settings") as mock_settings, \
+             patch("app.tasks.upload_to_webdav.requests.put") as mock_put, \
+             patch("app.tasks.upload_to_webdav.log_task_progress"):
+            
+            mock_settings.webdav_url = "https://webdav.example.com/"
+            mock_settings.webdav_username = "test_user"
+            mock_settings.webdav_password = "test_pass"
+            mock_settings.webdav_folder = "uploads"
+            mock_settings.webdav_verify_ssl = True
+            mock_settings.http_request_timeout = 30
+            
+            mock_response = Mock()
+            mock_response.status_code = 201
+            mock_put.return_value = mock_response
+            
+            result = upload_to_webdav.apply(args=[sample_text_file]).get()
+            
+            # Check return value structure
+            assert isinstance(result, dict)
+            assert "status" in result
+            assert "file" in result
+            assert "url" in result
+            assert result["status"] == "Completed"
+            assert result["file"] == sample_text_file
+
+    def test_module_importable(self):
+        """Test that upload_to_webdav module is importable."""
+        from app.tasks.upload_to_webdav import upload_to_webdav
+        assert callable(upload_to_webdav)
+
+    def test_task_has_retry_configuration(self):
+        """Test that the task has retry configuration from BaseTaskWithRetry."""
+        from app.tasks.upload_to_webdav import upload_to_webdav
+        
+        # BaseTaskWithRetry should provide retry configuration
+        assert hasattr(upload_to_webdav, 'max_retries')
+        # BaseTaskWithRetry configures 3 retries
+        assert upload_to_webdav.max_retries == 3