diff --git a/.changeset/llamacloud-local-file-name-extension.md b/.changeset/llamacloud-local-file-name-extension.md
new file mode 100644
index 000000000..09cc3db2b
--- /dev/null
+++ b/.changeset/llamacloud-local-file-name-extension.md
@@ -0,0 +1,10 @@
+---
+"@create-llama/llama-index-server": patch
+---
+
+fix: only strip the trailing extension when building the local LlamaCloud file name
+
+`get_local_file_name` used `str.replace(file_ext, "")`, which removes every
+occurrence of the extension string. For files whose stem also ends with the
+extension (e.g. `report.pdf.pdf`) this corrupted the stem (`report` instead of
+`report.pdf`). It now uses the root returned by `os.path.splitext`.
diff --git a/python/llama-index-server/llama_index/server/utils/llamacloud.py b/python/llama-index-server/llama_index/server/utils/llamacloud.py
index 42b37a870..842eaf407 100644
--- a/python/llama-index-server/llama_index/server/utils/llamacloud.py
+++ b/python/llama-index-server/llama_index/server/utils/llamacloud.py
@@ -22,8 +22,10 @@ def get_local_file_name(
     if llamacloud_file_name is None or pipeline_id is None:
         raise ValueError("Couldn't find llamacloud_file_name and pipeline_id")
     # Construct the local file name
-    file_ext = os.path.splitext(llamacloud_file_name)[1]
-    file_name = llamacloud_file_name.replace(file_ext, "")
+    file_root, file_ext = os.path.splitext(llamacloud_file_name)
+    # Only strip the trailing extension; using str.replace would remove every
+    # occurrence of the extension (e.g. "report.pdf.pdf" -> "report").
+    file_name = file_root
     sanitized_file_name = re.sub(r"[^A-Za-z0-9_\-]", "_", file_name)
     return f"{sanitized_file_name}_{pipeline_id}{file_ext}"
 
diff --git a/python/llama-index-server/tests/utils/test_llamacloud.py b/python/llama-index-server/tests/utils/test_llamacloud.py
new file mode 100644
index 000000000..7cf2ccb69
--- /dev/null
+++ b/python/llama-index-server/tests/utils/test_llamacloud.py
@@ -0,0 +1,37 @@
+from llama_index.server.utils.llamacloud import (
+    get_local_file_name,
+    is_llamacloud_file,
+)
+
+
+def test_get_local_file_name_single_extension() -> None:
+    assert (
+        get_local_file_name(llamacloud_file_name="report.pdf", pipeline_id="123")
+        == "report_123.pdf"
+    )
+
+
+def test_get_local_file_name_keeps_repeated_extension_in_stem() -> None:
+    # The stem also ends with the extension string. Only the trailing
+    # extension must be stripped, otherwise the stem is corrupted.
+    assert (
+        get_local_file_name(llamacloud_file_name="report.pdf.pdf", pipeline_id="123")
+        == "report_pdf_123.pdf"
+    )
+
+
+def test_get_local_file_name_extension_substring_in_stem() -> None:
+    assert (
+        get_local_file_name(llamacloud_file_name="backup.tar.tar", pipeline_id="abc")
+        == "backup_tar_abc.tar"
+    )
+
+
+def test_get_local_file_name_from_metadata() -> None:
+    metadata = {"file_name": "my.report.pdf.pdf", "pipeline_id": "p1"}
+    assert get_local_file_name(node_metadata=metadata) == "my_report_pdf_p1.pdf"
+
+
+def test_is_llamacloud_file() -> None:
+    assert is_llamacloud_file({"pipeline_id": "p1"}) is True
+    assert is_llamacloud_file({"file_name": "a.pdf"}) is False