diff --git a/src/embedding_client.py b/src/embedding_client.py
index 70f6b34a..1656338d 100644
--- a/src/embedding_client.py
+++ b/src/embedding_client.py
@@ -313,17 +313,23 @@ class _EmbeddingClient:
         """Return a prefix of `text` whose re-encoded token count fits the cap.
 
         `decode(ids[:n])` can re-encode to more than `n` tokens at BPE /
-        pre-tokenizer boundaries, so we re-encode after each slice and trim
-        again until the verified count fits. If a slice does not shrink the
-        count we drop one extra token so the loop cannot spin.
+        pre-tokenizer boundaries (a slice landing mid-character decodes to
+        replacement chars that cost tokens of their own), so we re-encode
+        after each slice and trim again until the verified count fits. Each
+        retry keeps strictly fewer tokens than the last, so the loop always
+        terminates instead of oscillating around the cap.
         """
         token_ids = self.encoding.encode(text)
+        keep = self.max_embedding_tokens
         while len(token_ids) > self.max_embedding_tokens:
-            keep = min(self.max_embedding_tokens, len(token_ids) - 1)
+            keep = min(keep, len(token_ids) - 1)
             if keep < 1:
                 return "", 0
             text = self.encoding.decode(token_ids[:keep])
             token_ids = self.encoding.encode(text)
+            # Guarantee forward progress: if this slice still re-encodes over
+            # the cap, the next one must be strictly smaller.
+            keep -= 1
         return text, len(token_ids)
 
     async def simple_batch_embed(
diff --git a/src/reconciler/sync_vectors.py b/src/reconciler/sync_vectors.py
index 68e9ac59..8f510f47 100644
--- a/src/reconciler/sync_vectors.py
+++ b/src/reconciler/sync_vectors.py
@@ -301,7 +301,14 @@ async def _sync_documents(
                 EmbeddingCallPurpose.VECTOR_SYNC.value,
                 parent_category="reconciliation",
             ):
-                new_embeddings = await embedding_client.simple_batch_embed(contents)
+                # Document content is stored whole, so an observation can be
+                # over the per-item embedding cap (the write path truncates the
+                # embedded prefix, not the stored text). Truncate here too:
+                # raising would drop every other document in this batch on
+                # every reconciler pass.
+                new_embeddings = await embedding_client.simple_batch_embed(
+                    contents, on_oversize="truncate"
+                )
 
             if len(new_embeddings) != len(docs_needing_embed):
                 logger.warning(
diff --git a/tests/deriver/test_vector_reconciliation.py b/tests/deriver/test_vector_reconciliation.py
index 5e2e4712..b22d71a8 100644
--- a/tests/deriver/test_vector_reconciliation.py
+++ b/tests/deriver/test_vector_reconciliation.py
@@ -551,7 +551,9 @@ class TestReEmbedding:
         # Mock embedding client to track batch calls
         batch_call_count = 0
 
-        async def track_batch_embed(contents: list[str]) -> list[list[float]]:
+        async def track_batch_embed(
+            contents: list[str], **_kwargs: object
+        ) -> list[list[float]]:
             nonlocal batch_call_count
             batch_call_count += 1
             return [[1.0] * 1536 for _ in contents]