diff --git a/.gitignore b/.gitignore
index c598b98..80a1db0 100644
--- a/.gitignore
+++ b/.gitignore
@@ -110,5 +110,6 @@ experiments/*
 !batdetect2_notebook.ipynb
 !batdetect2/models/*.pth.tar
 !tests/data/*.wav
+!tests/data/**/*.wav
 notebooks/lightning_logs
 example_data/preprocessed
diff --git a/tests/conftest.py b/tests/conftest.py
new file mode 100644
index 0000000..06f9ddc
--- /dev/null
+++ b/tests/conftest.py
@@ -0,0 +1,17 @@
+from pathlib import Path
+
+import pytest
+
+
+@pytest.fixture
+def data_dir() -> Path:
+    dir = Path(__file__).parent / "data"
+    assert dir.exists()
+    return dir
+
+
+@pytest.fixture
+def contrib_dir(data_dir) -> Path:
+    dir = data_dir / "contrib"
+    assert dir.exists()
+    return dir
diff --git a/tests/data/contrib/jeff37/0166_20240531_223911.wav b/tests/data/contrib/jeff37/0166_20240531_223911.wav
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diff --git a/tests/data/contrib/jeff37/0166_20240603_033731.wav b/tests/data/contrib/jeff37/0166_20240603_033731.wav
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diff --git a/tests/data/contrib/jeff37/0166_20240603_033937.wav b/tests/data/contrib/jeff37/0166_20240603_033937.wav
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diff --git a/tests/data/contrib/jeff37/0166_20240604_233500.wav b/tests/data/contrib/jeff37/0166_20240604_233500.wav
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diff --git a/tests/test_contrib.py b/tests/test_contrib.py
new file mode 100644
index 0000000..efb0531
--- /dev/null
+++ b/tests/test_contrib.py
@@ -0,0 +1,42 @@
+"""Test suite to ensure user provided files are correctly processed."""
+
+from pathlib import Path
+
+from click.testing import CliRunner
+
+from batdetect2.cli import cli
+
+runner = CliRunner()
+
+
+def test_files_negative_dimensions_are_not_allowed(
+    contrib_dir: Path,
+    tmp_path: Path,
+):
+    """This test stems from issue #31.
+
+    A user provided a set of files which which batdetect2 cli failed and
+    generated the following error message:
+
+        [2272] "Error processing file!: negative dimensions are not allowed"
+
+    This test ensures that the error message is not generated when running
+    batdetect2 cli with the same set of files.
+    """
+    path = contrib_dir / "jeff37"
+    assert path.exists()
+
+    results_dir = tmp_path / "results"
+    result = runner.invoke(
+        cli,
+        [
+            "detect",
+            str(path),
+            str(results_dir),
+            "0.3",
+        ],
+    )
+    assert result.exit_code == 0
+    assert results_dir.exists()
+    assert len(list(results_dir.glob("*.csv"))) == 3
+    assert len(list(results_dir.glob("*.json"))) == 3