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..1d78382b18 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,
             }
+            lowered_path = path.lower()
             for ext, dtype in mapping.items():
-                if path.endswith(ext):
+                if lowered_path.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..7774c29b71
--- /dev/null
+++ b/lib/crewai-tools/tests/rag/test_data_types.py
@@ -0,0 +1,74 @@
+"""Tests for file-type detection in ``DataTypes.from_content``.
+
+Extension detection must be case-insensitive so that files/URLs with
+uppercase or mixed-case extensions (e.g. ``report.PDF``) are routed to the
+correct loader instead of silently falling back to the plain-text loader.
+"""
+
+from pathlib import Path
+import tempfile
+
+import pytest
+
+from crewai_tools.rag.data_types import DataType, DataTypes
+
+
+class TestFileExtensionCaseInsensitivity:
+    """Local-file extension detection should ignore case."""
+
+    @pytest.mark.parametrize(
+        ("suffix", "expected"),
+        [
+            (".pdf", DataType.PDF_FILE),
+            (".PDF", DataType.PDF_FILE),
+            (".Pdf", DataType.PDF_FILE),
+            (".csv", DataType.CSV),
+            (".CSV", DataType.CSV),
+            (".json", DataType.JSON),
+            (".JSON", DataType.JSON),
+            (".xml", DataType.XML),
+            (".XML", DataType.XML),
+            (".docx", DataType.DOCX),
+            (".DOCX", DataType.DOCX),
+            (".mdx", DataType.MDX),
+            (".MDX", DataType.MDX),
+            (".md", DataType.MDX),
+            (".MD", DataType.MDX),
+            (".txt", DataType.TEXT_FILE),
+            (".TXT", DataType.TEXT_FILE),
+        ],
+    )
+    def test_local_file_extension_is_case_insensitive(
+        self, suffix: str, expected: DataType
+    ) -> None:
+        with tempfile.TemporaryDirectory() as tmpdir:
+            file_path = Path(tmpdir) / f"document{suffix}"
+            file_path.write_text("content")
+
+            assert DataTypes.from_content(str(file_path)) == expected
+
+    def test_uppercase_pdf_is_not_misdetected_as_text_file(self) -> None:
+        """Regression: an uppercase ``.PDF`` must not fall back to text_file."""
+        with tempfile.TemporaryDirectory() as tmpdir:
+            file_path = Path(tmpdir) / "report.PDF"
+            file_path.write_text("content")
+
+            assert DataTypes.from_content(str(file_path)) == DataType.PDF_FILE
+
+
+class TestUrlExtensionCaseInsensitivity:
+    """URL extension detection should ignore case."""
+
+    @pytest.mark.parametrize(
+        ("url", "expected"),
+        [
+            ("https://example.com/file.pdf", DataType.PDF_FILE),
+            ("https://example.com/file.PDF", DataType.PDF_FILE),
+            ("https://example.com/data.CSV", DataType.CSV),
+            ("https://example.com/data.JSON", DataType.JSON),
+        ],
+    )
+    def test_url_extension_is_case_insensitive(
+        self, url: str, expected: DataType
+    ) -> None:
+        assert DataTypes.from_content(url) == expected