diff --git a/paperqa/agents/search.py b/paperqa/agents/search.py
index f9625bf1..585f5391 100644
--- a/paperqa/agents/search.py
+++ b/paperqa/agents/search.py
@@ -353,6 +353,9 @@ async def maybe_get_manifest(filename: anyio.Path | None) -> dict[str, DocDetail
     return {}
 
 
+FAILED_DOCUMENT_ADD_ID = "ERROR"
+
+
 async def process_file(
     file_path: anyio.Path,
     search_index: SearchIndex,
@@ -382,7 +385,9 @@ async def process_file(
                 logger.exception(
                     f"Error parsing {file_name}, skipping index for this file."
                 )
-                (await search_index.index_files)[str(file_path)] = "ERROR"
+                (await search_index.index_files)[
+                    str(file_path)
+                ] = FAILED_DOCUMENT_ADD_ID
                 await search_index.save_index()
                 return
 
diff --git a/paperqa/readers.py b/paperqa/readers.py
index 0a4962bf..496b1f62 100644
--- a/paperqa/readers.py
+++ b/paperqa/readers.py
@@ -48,7 +48,8 @@ def chunk_pdf(
 
     if not parsed_text.content:
         raise ImpossibleParsingError(
-            "No text was parsed from the document: either empty or corrupted."
+            f"No text was parsed from the document named {doc.docname!r}, either empty"
+            " or corrupted."
         )
 
     for page_num, page_text in parsed_text.content.items():
@@ -117,17 +118,19 @@ def parse_text(
 
 
 def chunk_text(
-    parsed_text: ParsedText, doc: Doc, chunk_chars: int, overlap: int, use_tiktoken=True
+    parsed_text: ParsedText,
+    doc: Doc,
+    chunk_chars: int,
+    overlap: int,
+    use_tiktoken: bool = True,
 ) -> list[Text]:
     """Parse a document into chunks, based on tiktoken encoding.
 
     NOTE: We get some byte continuation errors.
-    Currently ignored, but should explore more to make sure we
-    don't miss anything.
+    Currently ignored, but should explore more to make sure we don't miss anything.
     """
     texts: list[Text] = []
     enc = tiktoken.get_encoding("cl100k_base")
-    split = []
 
     if not isinstance(parsed_text.content, str):
         raise NotImplementedError(
@@ -135,6 +138,11 @@ def chunk_text(
         )
 
     content = parsed_text.content if not use_tiktoken else parsed_text.encode_content()
+    if not content:  # Avoid div0 in token calculations
+        raise ImpossibleParsingError(
+            f"No text was parsed from the document named {doc.docname!r}, either empty"
+            " or corrupted."
+        )
 
     # convert from characters to chunks
     char_count = parsed_text.metadata.total_parsed_text_length  # e.g., 25,000
diff --git a/tests/stub_data/empty.txt b/tests/stub_data/empty.txt
new file mode 100644
index 00000000..e69de29b
diff --git a/tests/test_agents.py b/tests/test_agents.py
index 425c5685..c456a892 100644
--- a/tests/test_agents.py
+++ b/tests/test_agents.py
@@ -21,7 +21,7 @@
 from paperqa.agents import agent_query
 from paperqa.agents.env import settings_to_tools
 from paperqa.agents.models import AgentStatus, AnswerResponse, QueryRequest
-from paperqa.agents.search import get_directory_index
+from paperqa.agents.search import FAILED_DOCUMENT_ADD_ID, get_directory_index
 from paperqa.agents.tools import (
     EnvironmentState,
     GatherEvidence,
@@ -44,8 +44,12 @@ async def test_get_directory_index(agent_test_settings: Settings) -> None:
         "title",
         "year",
     ], "Incorrect fields in index"
-    # paper.pdf + flag_day.html + bates.txt + obama.txt
-    assert len(await index.index_files) == 4, "Incorrect number of index files"
+    # paper.pdf + empty.txt + flag_day.html + bates.txt + obama.txt,
+    # but empty.txt fails to be added
+    path_to_id = await index.index_files
+    assert (
+        sum(id_ != FAILED_DOCUMENT_ADD_ID for id_ in path_to_id.values()) == 4
+    ), "Incorrect number of parsed index files"
     results = await index.query(query="who is Frederick Bates?")
     paper_dir = cast(Path, agent_test_settings.paper_directory)
     assert results[0].docs.keys() == {md5sum((paper_dir / "bates.txt").absolute())}
@@ -63,8 +67,8 @@ async def test_get_directory_index_w_manifest(
         "title",
         "year",
     ], "Incorrect fields in index"
-    # paper.pdf + flag_day.html + bates.txt + obama.txt
-    assert len(await index.index_files) == 4, "Incorrect number of index files"
+    # paper.pdf + empty.txt + flag_day.html + bates.txt + obama.txt
+    assert len(await index.index_files) == 5, "Incorrect number of index files"
     results = await index.query(query="who is Frederick Bates?")
     top_result = next(iter(results[0].docs.values()))
     paper_dir = cast(Path, agent_test_settings.paper_directory)
diff --git a/tests/test_paperqa.py b/tests/test_paperqa.py
index 2284a3bc..c44adedd 100644
--- a/tests/test_paperqa.py
+++ b/tests/test_paperqa.py
@@ -837,13 +837,15 @@ def test_pdf_reader_match_doc_details(stub_data_dir: Path) -> None:
     assert "yes" in answer.answer or "Yes" in answer.answer
 
 
-@pytest.mark.flaky(reruns=3, only_rerun=["AssertionError"])
+@pytest.mark.flaky(reruns=5, only_rerun=["AssertionError"])
 def test_fileio_reader_pdf(stub_data_dir: Path) -> None:
     with (stub_data_dir / "paper.pdf").open("rb") as f:
         docs = Docs()
         docs.add_file(f, "Wellawatte et al, XAI Review, 2023")
         answer = docs.query("Are counterfactuals actionable?[yes/no]")
-        assert "yes" in answer.answer or "Yes" in answer.answer
+        assert any(
+            w in answer.answer for w in ("yes", "Yes")
+        ), f"Incorrect answer: {answer.answer}"
 
 
 def test_fileio_reader_txt(stub_data_dir: Path) -> None: