diff --git a/outlines/fsm/json_schema.py b/outlines/fsm/json_schema.py
index d96597d4c..2c53fd240 100644
--- a/outlines/fsm/json_schema.py
+++ b/outlines/fsm/json_schema.py
@@ -195,13 +195,7 @@ def to_regex(
             to_regex(resolver, t, whitespace_pattern) for t in instance["oneOf"]
         ]
 
-        xor_patterns = []
-        # json schema validation ensured there is no overlapping schemas in oneOf
-        for subregex in subregexes:
-            other_subregexes = filter(lambda r: r != subregex, subregexes)
-            other_subregexes_str = "|".join([f"{s}" for s in other_subregexes])
-            negative_lookahead = f"(?!.*({other_subregexes_str}))"
-            xor_patterns.append(f"({subregex}){negative_lookahead}")
+        xor_patterns = [f"(?:{subregex})" for subregex in subregexes]
 
         return rf"({'|'.join(xor_patterns)})"
 
diff --git a/tests/fsm/test_json_schema.py b/tests/fsm/test_json_schema.py
index 5b3ad9e39..b992f7aa5 100644
--- a/tests/fsm/test_json_schema.py
+++ b/tests/fsm/test_json_schema.py
@@ -1,9 +1,10 @@
 import json
 import re
-from typing import List
+from typing import List, Literal, Union
 
+import interegular
 import pytest
-from pydantic import BaseModel, constr
+from pydantic import BaseModel, Field, constr
 
 from outlines.fsm.json_schema import (
     BOOLEAN,
@@ -321,7 +322,7 @@ def test_match_number(pattern, does_match):
                 "title": "Foo",
                 "oneOf": [{"type": "string"}, {"type": "number"}, {"type": "boolean"}],
             },
-            rf"(({STRING})(?!.*({NUMBER}|{BOOLEAN}))|({NUMBER})(?!.*({STRING}|{BOOLEAN}))|({BOOLEAN})(?!.*({STRING}|{NUMBER})))",
+            rf'((?:"{STRING_INNER}*")|(?:{NUMBER})|(?:{BOOLEAN}))',
             [
                 ("12.3", True),
                 ("true", True),
@@ -750,3 +751,27 @@ class MockModel(BaseModel):
         assert match_default_ws is None
 
     assert re.fullmatch(pattern, mock_result_maybe_ws)
+
+
+def test_one_of_doesnt_produce_illegal_lookaround():
+    """Reproduces failure in https://github.com/outlines-dev/outlines/issues/823"""
+
+    class Cat(BaseModel):
+        pet_type: Literal["cat"]
+        meows: int
+
+    class Dog(BaseModel):
+        pet_type: Literal["dog"]
+        barks: float
+
+    class Model(BaseModel):
+        pet: Union[Cat, Dog] = Field(..., discriminator="pet_type")
+        n: int
+
+    json_schema = Model.schema_json()
+
+    json_schema = Model.schema_json()
+    pattern = build_regex_from_schema(json_schema, whitespace_pattern=None)
+
+    # check if the pattern uses lookarounds incompatible with interegular.Pattern.to_fsm()
+    interegular.parse_pattern(pattern).to_fsm()