diff --git a/lib/crewai-tools/src/crewai_tools/rag/data_types.py b/lib/crewai-tools/src/crewai_tools/rag/data_types.py
index 27ee48abb0..94d1dd58ba 100644
--- a/lib/crewai-tools/src/crewai_tools/rag/data_types.py
+++ b/lib/crewai-tools/src/crewai_tools/rag/data_types.py
@@ -123,8 +123,9 @@ def get_file_type(path: str) -> DataType | None:
                 ".xml": DataType.XML,
                 ".txt": DataType.TEXT_FILE,
             }
+            path_lower = path.lower()
             for ext, dtype in mapping.items():
-                if path.endswith(ext):
+                if path_lower.endswith(ext):
                     return dtype
             return None
 
diff --git a/lib/crewai-tools/tests/rag/test_data_types.py b/lib/crewai-tools/tests/rag/test_data_types.py
new file mode 100644
index 0000000000..41e8a35fc2
--- /dev/null
+++ b/lib/crewai-tools/tests/rag/test_data_types.py
@@ -0,0 +1,60 @@
+import os
+import tempfile
+from collections.abc import Callable, Iterator
+
+from crewai_tools.rag.data_types import DataType, DataTypes
+import pytest
+
+
+@pytest.fixture
+def temp_file() -> Iterator[Callable[[str], str]]:
+    created_files: list[str] = []
+
+    def _create(suffix: str) -> str:
+        f = tempfile.NamedTemporaryFile(mode="w", suffix=suffix, delete=False)
+        f.write("content")
+        f.close()
+        created_files.append(f.name)
+        return f.name
+
+    yield _create
+
+    for path in created_files:
+        os.unlink(path)
+
+
+class TestDataTypesFromContent:
+    @pytest.mark.parametrize(
+        "suffix,expected",
+        [
+            (".pdf", DataType.PDF_FILE),
+            (".PDF", DataType.PDF_FILE),
+            (".csv", DataType.CSV),
+            (".CSV", DataType.CSV),
+            (".docx", DataType.DOCX),
+            (".DOCX", DataType.DOCX),
+            (".json", DataType.JSON),
+            (".Json", DataType.JSON),
+            (".xml", DataType.XML),
+            (".XML", DataType.XML),
+            (".md", DataType.MDX),
+            (".MD", DataType.MDX),
+        ],
+    )
+    def test_file_extension_detection_is_case_insensitive(
+        self, temp_file: Callable[[str], str], suffix: str, expected: DataType
+    ) -> None:
+        path = temp_file(suffix)
+        assert DataTypes.from_content(path) == expected
+
+    def test_uppercase_pdf_url_is_detected_as_pdf(self) -> None:
+        assert (
+            DataTypes.from_content("https://example.com/file.PDF")
+            == DataType.PDF_FILE
+        )
+
+    def test_lowercase_pdf_url_is_detected_as_pdf(self) -> None:
+        assert (
+            DataTypes.from_content("https://example.com/file.pdf")
+            == DataType.PDF_FILE
+        )