diff --git a/.jules/bolt.md b/.jules/bolt.md
new file mode 100644
index 0000000..f987448
--- /dev/null
+++ b/.jules/bolt.md
@@ -0,0 +1,3 @@
+## 2024-08-25 - [Memoizing Deterministic Regex Compilations]
+**Learning:** NLP and text-processing pipelines, especially within `openmed.clinical`, heavily rely on compiling sets of strings into regex patterns (`_cue_pattern`). Without caching, iterating over sentences/documents triggers repetitive regex parsing, slowing down throughput dramatically.
+**Action:** Always memoize deterministic regex compilations and lexicon generation (e.g., using `@functools.lru_cache`) with tuple parameters instead of lists to prevent severe performance bottlenecks during repeated string/span evaluations.
diff --git a/openmed/openmed/clinical/context.py b/openmed/openmed/clinical/context.py
index 9fd11df..e78f5ad 100644
--- a/openmed/openmed/clinical/context.py
+++ b/openmed/openmed/clinical/context.py
@@ -35,6 +35,7 @@
 
 from __future__ import annotations
 
+import functools
 import re
 from collections.abc import Iterable, Iterator, Mapping, Sequence
 from dataclasses import dataclass, replace
@@ -154,6 +155,7 @@ class _CompiledContextLexicon:
     backward_context_cues: frozenset[str]
 
 
+@functools.lru_cache
 def _compiled_context_lexicon(language: str | None = None) -> _CompiledContextLexicon:
     lexicon = get_clinical_cue_lexicon(language)
     token_boundaries = lexicon.token_boundaries
diff --git a/openmed/openmed/clinical/status_vocab.py b/openmed/openmed/clinical/status_vocab.py
index 3b87adb..6020ece 100644
--- a/openmed/openmed/clinical/status_vocab.py
+++ b/openmed/openmed/clinical/status_vocab.py
@@ -186,7 +186,7 @@ def _cue_matches(text: str, cue: object) -> bool:
     return _cue_pattern(normalized_cue).search(text) is not None
 
 
-@lru_cache(maxsize=512)
+@lru_cache(maxsize=1024)
 def _cue_pattern(cue: str) -> re.Pattern[str]:
     escaped = re.escape(cue).replace(r"\ ", r"\s+")
     prefix = r"(?<!\w)"