diff --git a/test/e2e/conftest.py b/test/e2e/conftest.py
index af56251..bc193ef 100644
--- a/test/e2e/conftest.py
+++ b/test/e2e/conftest.py
@@ -4,7 +4,6 @@
 from test.e2e.env_config import PORT
 from test.e2e.pageobjects.create_paste_page import CreatePastePage
 from typing import Generator
-
 import pytest
 from playwright.sync_api import Page
 
@@ -16,7 +15,16 @@ def application() -> Generator[None, None, None]:
     # Before All
     log.info(f"Starting Pinnwand application on port {PORT}")
     proc = subprocess.Popen(
-        [sys.executable, "-m", "pinnwand", "http", "--port", str(PORT)]
+        [
+            sys.executable,
+            "-m",
+            "pinnwand",
+            "--configuration-path",
+            "test/e2e/pinnwand.toml",
+            "http",
+            "--port",
+            str(PORT),
+        ]
     )
     yield
     # After All
diff --git a/test/e2e/pageobjects/create_paste_page.py b/test/e2e/pageobjects/create_paste_page.py
index a104600..7804b7b 100644
--- a/test/e2e/pageobjects/create_paste_page.py
+++ b/test/e2e/pageobjects/create_paste_page.py
@@ -18,6 +18,7 @@ def __init__(self, page: Page) -> None:
         self.paste_input = page.locator(".file-part textarea")
         self.submit_button = page.locator(".paste-submit button[type=submit]")
         self.add_another_paste_button = page.locator("button.add")
+        self.file_input = page.locator("#file-input")
 
     def open(self):
         log.info(f"Opening Pinnwand at {self.url}")
@@ -35,6 +36,10 @@ def click_add_another_file_button(self):
         log.info("Clicking Add Another Paste Button")
         self.add_another_paste_button.click()
 
+    def add_file_to_file_input(self, file_paths):
+        log.info("Adding file for uploading")
+        self.file_input.set_input_files(file_paths)
+
     # Step sequences
     def paste_random_text(self, paste_number=0):
         paste_text = string.ascii_letters + string.digits
diff --git a/test/e2e/pinnwand.toml b/test/e2e/pinnwand.toml
new file mode 100644
index 0000000..12b33f8
--- /dev/null
+++ b/test/e2e/pinnwand.toml
@@ -0,0 +1,11 @@
+ratelimit.read.capacity = 200
+ratelimit.read.consume = 1
+ratelimit.read.refill = 10
+
+ratelimit.create.capacity = 200
+ratelimit.create.consume = 1
+ratelimit.create.refill = 10
+
+ratelimit.delete.capacity = 200
+ratelimit.delete.consume = 1
+ratelimit.delete.refill = 10
\ No newline at end of file
diff --git a/test/e2e/testscenarios/test_delete_paste.py b/test/e2e/testscenarios/test_delete_paste.py
index d861538..01a1e13 100644
--- a/test/e2e/testscenarios/test_delete_paste.py
+++ b/test/e2e/testscenarios/test_delete_paste.py
@@ -1,4 +1,3 @@
-from test.e2e.conftest import create_paste_page
 from test.e2e.pageobjects.create_paste_page import CreatePastePage
 from test.e2e.pageobjects.error_page import ErrorPage
 from test.e2e.pageobjects.view_paste_page import ViewPastePage
diff --git a/test/e2e/testscenarios/test_upload_files.py b/test/e2e/testscenarios/test_upload_files.py
new file mode 100644
index 0000000..6e417fe
--- /dev/null
+++ b/test/e2e/testscenarios/test_upload_files.py
@@ -0,0 +1,40 @@
+from test.e2e.pageobjects.create_paste_page import CreatePastePage
+from test.e2e.pageobjects.view_paste_page import ViewPastePage
+from test.e2e.utils.file_utils import create_random_file
+import pytest
+from playwright.sync_api import Page
+
+
+@pytest.mark.e2e
+def test_upload_single_file(page: Page, create_paste_page: CreatePastePage):
+    with create_random_file() as temp:
+        file_content = temp.read().decode()
+        create_paste_page.add_file_to_file_input(temp.name)
+        create_paste_page.should_have_value_in_paste_input(file_content)
+        create_paste_page.click_submit()
+
+    view_paste_page = ViewPastePage(page)
+    view_paste_page.should_be_opened()
+    view_paste_page.should_have_pasted_text(file_content)
+
+
+@pytest.mark.e2e
+def test_upload_multiple_files(page: Page, create_paste_page: CreatePastePage):
+    with create_random_file() as first_temp, create_random_file() as second_temp:
+        first_file_content = first_temp.read().decode()
+        second_file_content = second_temp.read().decode()
+        create_paste_page.add_file_to_file_input(
+            [first_temp.name, second_temp.name]
+        )
+        create_paste_page.should_have_value_in_paste_input(
+            first_file_content, paste_number=0
+        )
+        create_paste_page.should_have_value_in_paste_input(
+            second_file_content, paste_number=1
+        )
+        create_paste_page.click_submit()
+
+    view_paste_page = ViewPastePage(page)
+    view_paste_page.should_be_opened()
+    view_paste_page.should_have_pasted_text(first_file_content, paste_number=0)
+    view_paste_page.should_have_pasted_text(second_file_content, paste_number=1)
diff --git a/test/e2e/utils/file_utils.py b/test/e2e/utils/file_utils.py
new file mode 100644
index 0000000..dd0a152
--- /dev/null
+++ b/test/e2e/utils/file_utils.py
@@ -0,0 +1,16 @@
+from test.e2e.utils.string_utils import random_string
+import tempfile
+import os
+from contextlib import contextmanager
+
+
+@contextmanager
+def create_random_file():
+    temp = tempfile.NamedTemporaryFile(suffix=".txt", delete=False)
+    temp.write(random_string().encode())
+    temp.seek(0)
+    try:
+        yield temp
+    finally:
+        temp.close()
+        os.remove(temp.name)
diff --git a/test/e2e/utils/string_utils.py b/test/e2e/utils/string_utils.py
new file mode 100644
index 0000000..0a8861f
--- /dev/null
+++ b/test/e2e/utils/string_utils.py
@@ -0,0 +1,11 @@
+import random
+import string
+
+
+def random_string(size=1000) -> str:
+    return "".join(
+        [
+            random.choice(string.ascii_letters + string.digits)
+            for i in range(size)
+        ]
+    )