diff --git a/tests/api/v1/software/software-header-2.swu b/tests/api/v1/software/software-header-2.swu
new file mode 100644
index 00000000..4fa6112b
Binary files /dev/null and b/tests/api/v1/software/software-header-2.swu differ
diff --git a/tests/api/v1/software/test_routes.py b/tests/api/v1/software/test_routes.py
index 5eb686e8..41bcbbc1 100644
--- a/tests/api/v1/software/test_routes.py
+++ b/tests/api/v1/software/test_routes.py
@@ -1,6 +1,8 @@
 import pytest
 from anyio import Path, open_file
 
+from goosebit.db.models import Rollout
+
 
 @pytest.mark.asyncio
 async def test_create_software_local(async_client, test_data):
@@ -16,6 +18,21 @@ async def test_create_software_local(async_client, test_data):
     assert software["id"] == 4
 
 
+@pytest.mark.asyncio
+async def test_create_software_local_twice(async_client, test_data):
+    resolved = await Path(__file__).resolve()
+    path = resolved.parent / "software-header.swu"
+    with open(path, "rb") as file:
+        files = {"file": file}
+        response = await async_client.post(f"/api/v1/software", files=files)
+    assert response.status_code == 200
+
+    with open(path, "rb") as file:
+        files = {"file": file}
+        response = await async_client.post(f"/api/v1/software", files=files)
+    assert response.status_code == 409
+
+
 @pytest.mark.asyncio
 async def test_create_software_remote(async_client, httpserver, test_data):
     resolved = await Path(__file__).resolve()
@@ -31,3 +48,64 @@ async def test_create_software_remote(async_client, httpserver, test_data):
     assert response.status_code == 200
     software = response.json()
     assert software["id"] == 4
+
+
+@pytest.mark.asyncio
+async def test_create_software_remote_twice_same_content_different_url(async_client, httpserver, test_data):
+    response = await _upload_software(async_client, httpserver, "software-header.swu", "/software-header.swu")
+    assert response.status_code == 200
+
+    response = await _upload_software(async_client, httpserver, "software-header.swu", "/software-header-2.swu")
+    assert response.status_code == 409
+
+
+@pytest.mark.asyncio
+async def test_create_software_remote_twice_different_content_different_url(async_client, httpserver, test_data):
+    response = await _upload_software(async_client, httpserver, "software-header.swu", "/software-header.swu")
+    assert response.status_code == 200
+    software = response.json()
+    software_id = software["id"]
+
+    response = await _upload_software(async_client, httpserver, "software-header-2.swu", "/software-header-2.swu")
+    assert response.status_code == 200
+    software = response.json()
+    assert software_id != software["id"], "added second software"
+
+
+@pytest.mark.asyncio
+async def test_create_software_remote_twice_different_content_same_url(async_client, httpserver, test_data):
+    response = await _upload_software(async_client, httpserver, "software-header.swu", "/software-header.swu")
+    assert response.status_code == 200
+    software = response.json()
+    software_id = software["id"]
+
+    response = await _upload_software(async_client, httpserver, "software-header-2.swu", "/software-header.swu")
+    assert response.status_code == 200
+    software = response.json()
+    assert software_id != software["id"], "added second software"
+
+
+@pytest.mark.asyncio
+async def test_create_software_remote_twice_different_content_same_url_referenced_by_rollout(
+    async_client, httpserver, test_data
+):
+    response = await _upload_software(async_client, httpserver, "software-header.swu", "/software-header.swu")
+    assert response.status_code == 200
+    software = response.json()
+    software_id = software["id"]
+
+    await Rollout.create(name=f"Test rollout", software_id=software_id)
+
+    response = await _upload_software(async_client, httpserver, "software-header-2.swu", "/software-header.swu")
+    assert response.status_code == 409
+
+
+async def _upload_software(async_client, httpserver, software_file, download_url):
+    resolved = await Path(__file__).resolve()
+    path = resolved.parent / software_file
+    with open(path, "rb") as file:
+        byte_array = file.read()
+    httpserver.expect_request(download_url).respond_with_data(byte_array)
+    software_url = httpserver.url_for(download_url)
+    response = await async_client.post(f"/api/v1/software", data={"url": software_url})
+    return response