diff --git a/.docker/docker-compose.ci-test.yml b/.docker/docker-compose.ci-test.yml
index e47ea4a..c01b639 100644
--- a/.docker/docker-compose.ci-test.yml
+++ b/.docker/docker-compose.ci-test.yml
@@ -4,9 +4,9 @@
 
 version: "3"
 services:
-  gotenberg:
+  gotenberg-client-test-server:
     image: docker.io/gotenberg/gotenberg:7.9.2
-    hostname: gotenberg
-    container_name: gotenberg
+    hostname: gotenberg-client-test-server
+    container_name: gotenberg-client-test-server
     network_mode: host
     restart: unless-stopped
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index d166e59..0c7e7a0 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -64,6 +64,11 @@ jobs:
         docker compose --file ${GITHUB_WORKSPACE}/.docker/docker-compose.ci-test.yml up --detach
         echo "Wait for container to be started"
         sleep 5
+    -
+      name: Install poppler-utils
+      run: |
+        sudo apt-get update
+        sudo apt-get install --yes --no-install-reccomends poppler-utils
     -
       name: Set up Python ${{ matrix.python-version }}
       uses: actions/setup-python@v4
@@ -72,7 +77,9 @@ jobs:
         cache: 'pip'
     -
       name: Install Hatch
-      run: pip install --upgrade hatch
+      run: |
+        python3 -m pip install --upgrade pip
+        pip install --upgrade hatch
     -
       name: Run tests
       run: hatch run cov
diff --git a/CHANGELOG.md b/CHANGELOG.md
index de445a1..97c805c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,12 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## [Unreleased]
+
+### Fixed
+
+- An issue with the sorting of merging PDFs. Expanded testing to cover the merged ordering
+
 ## [0.2.0] - 2023-10-16
 
 ### Added
diff --git a/src/gotenberg_client/_base.py b/src/gotenberg_client/_base.py
index 41a69e8..4beb317 100644
--- a/src/gotenberg_client/_base.py
+++ b/src/gotenberg_client/_base.py
@@ -79,23 +79,22 @@ def get_files(self) -> RequestFiles:
         files = {}
         for filename in self._file_map:
             file_path = self._file_map[filename]
-            # Gotenberg requires these to have the specific name
-            filepath_name = filename if filename in {"index.html", "header.html", "footer.html"} else file_path.name
 
             # Helpful but not necessary to provide the mime type when possible
             mime_type = guess_mime_type(file_path)
             if mime_type is not None:
                 files.update(
-                    {filepath_name: (filepath_name, self._stack.enter_context(file_path.open("rb")), mime_type)},
+                    {filename: (filename, self._stack.enter_context(file_path.open("rb")), mime_type)},
                 )
             else:  # pragma: no cover
-                files.update({filepath_name: (filepath_name, self._stack.enter_context(file_path.open("rb")))})  # type: ignore
+                files.update({filename: (filename, self._stack.enter_context(file_path.open("rb")))})  # type: ignore
         return files
 
     def _add_file_map(self, filepath: Path, name: Optional[str] = None) -> None:
         """
         Small helper to handle bookkeeping of files for later opening.  The name is
         optional to support those things which are required to have a certain name
+        generally for ordering or just to be found at all
         """
         if name is None:
             name = filepath.name
diff --git a/src/gotenberg_client/_merge.py b/src/gotenberg_client/_merge.py
index 52848a1..70ff94e 100644
--- a/src/gotenberg_client/_merge.py
+++ b/src/gotenberg_client/_merge.py
@@ -4,6 +4,8 @@
 from pathlib import Path
 from typing import List
 
+from httpx import Client
+
 from gotenberg_client._base import BaseApi
 from gotenberg_client._base import BaseRoute
 
@@ -13,15 +15,20 @@ class MergeRoute(BaseRoute):
     Handles the merging of a given set of files
     """
 
+    def __init__(self, client: Client, api_route: str) -> None:
+        super().__init__(client, api_route)
+        self._next = 1
+
     def merge(self, files: List[Path]) -> "MergeRoute":
         """
         Adds the given files into the file mapping.  This method will maintain the
         ordering of the list.  Calling this method multiple times may not merge
         in the expected ordering
         """
-        for idx, filepath in enumerate(files):
+        for filepath in files:
             # Include index to enforce ordering
-            self._add_file_map(filepath, f"{idx}_{filepath.name}")
+            self._add_file_map(filepath, f"{self._next}_{filepath.name}")
+            self._next += 1
         return self
 
 
diff --git a/src/gotenberg_client/_types_compat.py b/src/gotenberg_client/_types_compat.py
index 91bfbc1..8ccf339 100644
--- a/src/gotenberg_client/_types_compat.py
+++ b/src/gotenberg_client/_types_compat.py
@@ -4,7 +4,7 @@
 
 import sys
 
-if sys.version_info >= (3, 11):
+if sys.version_info >= (3, 11):  # pragma: no cover
     from typing import Self
-else:
+else:  # pragma: no cover
     from typing_extensions import Self  # noqa: F401
diff --git a/src/gotenberg_client/_utils.py b/src/gotenberg_client/_utils.py
index eec25ff..5c80146 100644
--- a/src/gotenberg_client/_utils.py
+++ b/src/gotenberg_client/_utils.py
@@ -19,7 +19,7 @@ def optional_to_form(value: Optional[Union[bool, int, float, str]], name: str) -
         return {name: str(value).lower()}
 
 
-def guess_mime_type_stdlib(url: Path) -> Optional[str]:
+def guess_mime_type_stdlib(url: Path) -> Optional[str]:  # pragma: no cover
     """
     Uses the standard library to guess a mimetype
     """
diff --git a/tests/samples/a_merge_second.pdf b/tests/samples/a_merge_second.pdf
new file mode 100644
index 0000000..2955c8d
Binary files /dev/null and b/tests/samples/a_merge_second.pdf differ
diff --git a/tests/samples/sample1.pdf b/tests/samples/sample1.pdf
old mode 100755
new mode 100644
diff --git a/tests/samples/z_first_merge.pdf b/tests/samples/z_first_merge.pdf
new file mode 100644
index 0000000..4f74613
Binary files /dev/null and b/tests/samples/z_first_merge.pdf differ
diff --git a/tests/test_merge.py b/tests/test_merge.py
index fc869fc..3239dba 100644
--- a/tests/test_merge.py
+++ b/tests/test_merge.py
@@ -1,7 +1,7 @@
 import shutil
+import subprocess
 import tempfile
 from pathlib import Path
-from typing import List
 
 import pikepdf
 import pytest
@@ -15,18 +15,27 @@
 from tests.utils import call_run_with_server_error_handling
 
 
-@pytest.fixture()
-def create_files():
+def extract_text(pdf_path: Path) -> str:
     """
-    Creates 2 files in a temporary directory and cleans them up
-    after their use
+    Using pdftotext from poppler, extracts the text of a PDF into a file,
+    then reads the file contents and returns it
     """
-    temp_dir = Path(tempfile.mkdtemp())
-    test_file = SAMPLE_DIR / "sample1.pdf"
-    other_test_file = temp_dir / "sample2.pdf"
-    other_test_file.write_bytes(test_file.read_bytes())
-    yield [test_file, other_test_file]
-    shutil.rmtree(temp_dir, ignore_errors=True)
+    with tempfile.NamedTemporaryFile(
+        mode="w+",
+    ) as tmp:
+        subprocess.run(
+            [  # noqa: S603
+                shutil.which("pdftotext"),
+                "-q",
+                "-layout",
+                "-enc",
+                "UTF-8",
+                str(pdf_path),
+                tmp.name,
+            ],
+            check=True,
+        )
+        return tmp.read()
 
 
 class TestMergePdfs:
@@ -37,12 +46,15 @@ class TestMergePdfs:
     def test_merge_files_pdf_a(
         self,
         client: GotenbergClient,
-        create_files: List[Path],
         gt_format: PdfAFormat,
         pike_format: str,
     ):
         with client.merge.merge() as route:
-            resp = call_run_with_server_error_handling(route.merge(create_files).pdf_format(gt_format))
+            resp = call_run_with_server_error_handling(
+                route.merge([SAMPLE_DIR / "z_first_merge.pdf", SAMPLE_DIR / "a_merge_second.pdf"]).pdf_format(
+                    gt_format,
+                ),
+            )
 
         assert resp.status_code == codes.OK
         assert "Content-Type" in resp.headers
@@ -58,14 +70,31 @@ def test_merge_files_pdf_a(
         if SAVE_OUTPUTS:
             (SAVE_DIR / f"test_libre_office_convert_xlsx_format_{pike_format}.pdf").write_bytes(resp.content)
 
-    def test_pdf_a_multiple_file(
+    def test_merge_multiple_file(
         self,
         client: GotenbergClient,
-        create_files: List[Path],
     ):
-        with client.merge.merge() as route:
-            resp = call_run_with_server_error_handling(route.merge(create_files))
+        if shutil.which("pdftotext") is None:
+            pytest.skip("No pdftotext executable found")
+        else:
+            with client.merge.merge() as route:
+                # By default, these would not merge correctly
+                route.merge([SAMPLE_DIR / "z_first_merge.pdf", SAMPLE_DIR / "a_merge_second.pdf"])
+                resp = call_run_with_server_error_handling(route)
+
+                assert resp.status_code == codes.OK
+                assert "Content-Type" in resp.headers
+                assert resp.headers["Content-Type"] == "application/pdf"
+
+                with tempfile.NamedTemporaryFile(mode="wb") as tmp:
+                    tmp.write(resp.content)
+
+                    text = extract_text(tmp.name)
+                    lines = text.split("\n")
+                    # Extra is empty line
+                    assert len(lines) == 3
+                    assert "first PDF to be merged." in lines[0]
+                    assert "second PDF to be merged." in lines[1]
 
-            assert resp.status_code == codes.OK
-            assert "Content-Type" in resp.headers
-            assert resp.headers["Content-Type"] == "application/pdf"
+                if SAVE_OUTPUTS:
+                    (SAVE_DIR / "test_pdf_a_multiple_file.pdf").write_bytes(resp.content)
diff --git a/tests/utils.py b/tests/utils.py
index 0db432b..29f97d7 100644
--- a/tests/utils.py
+++ b/tests/utils.py
@@ -33,16 +33,16 @@ def call_run_with_server_error_handling(route: BaseRoute) -> Response:
     one attempt to parse.
 
     This will wait the following:
-        - Attempt 1 - 20s following failure
-        - Attempt 2 - 40s following failure
-        - Attempt 3 - 80s following failure
-        - Attempt 4 - 160s
-        - Attempt 5 - 320s
+        - Attempt 1 - 5s following failure
+        - Attempt 2 - 10s following failure
+        - Attempt 3 - 20s following failure
+        - Attempt 4 - 40s following failure
+        - Attempt 5 - 80s following failure
 
     """
     result = None
     succeeded = False
-    retry_time = 20.0
+    retry_time = 5.0
     retry_count = 0
     max_retry_count = 5