diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5a18a66b74..47f7271960 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,10 @@
+## 0.27.24
+
+### Fixes
+
+- **Reject a negative `overlap`.** `ChunkingOptions` validated `new_after_n_chars` and `new_after_n_tokens` but not `overlap`, so a negative value silently corrupted output: on the character-split path the remainder started past the end of the fragment and dropped that many characters at every split boundary, and with `overlap_all=True` the tail slice ran forward and repeated most of the chunk. It now raises `ValueError`, matching the sibling options.
+
+
 ## 0.27.23
 
 ### Fixes
diff --git a/test_unstructured/chunking/test_base.py b/test_unstructured/chunking/test_base.py
index fcf0099b32..4c3bcd9c91 100644
--- a/test_unstructured/chunking/test_base.py
+++ b/test_unstructured/chunking/test_base.py
@@ -172,6 +172,22 @@ def it_rejects_new_after_n_chars_for_n_less_than_zero(self, n_chars: int):
         ):
             ChunkingOptions(new_after_n_chars=n_chars)._validate()
 
+    @pytest.mark.parametrize("overlap", [-1, -5])
+    def it_rejects_overlap_for_n_less_than_zero(self, overlap: int):
+        """A negative `overlap` silently corrupts chunk text, so reject it at validation.
+
+        On the character-split path `_TextSplitter.__call__` computes the remainder as
+        `s[maxlen - overlap:]`, so a negative overlap starts the remainder *after* the end of the
+        fragment and drops that many characters of the document at every split boundary. With
+        `overlap_all=True`, `PreChunk.overlap_tail` computes `self._text[-overlap:]`, which for a
+        negative overlap is a forward slice that repeats nearly the whole chunk in the next one.
+        """
+        with pytest.raises(
+            ValueError,
+            match=f"'overlap' argument must be >= 0, got {overlap}",
+        ):
+            ChunkingOptions(overlap=overlap)._validate()
+
     def it_rejects_overlap_not_less_than_max_characters(self):
         with pytest.raises(
             ValueError,
diff --git a/unstructured/__version__.py b/unstructured/__version__.py
index 1f3fae62c1..48bb3c3063 100644
--- a/unstructured/__version__.py
+++ b/unstructured/__version__.py
@@ -1 +1 @@
-__version__ = "0.27.23"  # pragma: no cover
+__version__ = "0.27.24"  # pragma: no cover
diff --git a/unstructured/chunking/base.py b/unstructured/chunking/base.py
index f2a6c1fd9f..5bbcc75c53 100644
--- a/unstructured/chunking/base.py
+++ b/unstructured/chunking/base.py
@@ -391,6 +391,15 @@ def _validate(self) -> None:
                 " adjacent elements"
             )
 
+        # -- a negative `overlap` is a caller mistake, not a smaller overlap: on the
+        # -- character-split path it moves the remainder's start past the end of the fragment and
+        # -- silently deletes that many characters from the document, and with `overlap_all=True`
+        # -- `_text[-overlap:]` becomes a forward slice that repeats most of the chunk instead of
+        # -- its tail. Reject it here, as `new_after_n_chars` already is.
+        overlap_arg = self._kwargs.get("overlap")
+        if overlap_arg is not None and overlap_arg < 0:
+            raise ValueError(f"'overlap' argument must be >= 0, got {overlap_arg}")
+
         # -- overlap must be less than max-chars or the chunk text will never be consumed --
         if self.overlap >= hard_max:
             raise ValueError(