diff --git a/.jules/bolt.md b/.jules/bolt.md
new file mode 100644
index 0000000..4ae275d
--- /dev/null
+++ b/.jules/bolt.md
@@ -0,0 +1,3 @@
+## 2025-10-31 - Memoizing Lexicon Regex Compilations
+**Learning:** In the openmed NLP pipelines (e.g., `openmed.clinical.context`), deterministic regex compilations (`_compiled_context_lexicon`) and lexicon generation can cause severe performance bottlenecks during repeated evaluations across text spans.
+**Action:** Always memoize deterministic lexicon and regex compilations (using `@functools.lru_cache`) when processing spans or lexicons dynamically in text pipelines.
diff --git a/openmed/openmed/clinical/context.py b/openmed/openmed/clinical/context.py
index 9fd11df..439abc2 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(maxsize=16)
 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/experiencer.py b/openmed/openmed/clinical/experiencer.py
index 8373a72..be1b6a8 100644
--- a/openmed/openmed/clinical/experiencer.py
+++ b/openmed/openmed/clinical/experiencer.py
@@ -22,6 +22,7 @@
 
 from __future__ import annotations
 
+import functools
 import re
 from collections.abc import Mapping
 from dataclasses import dataclass, replace
@@ -106,6 +107,7 @@
 _CLAUSE_BOUNDARY_RE = re.compile(r"[.!?;]")
 
 
+@functools.lru_cache(maxsize=512)
 def _cue_pattern(cues: tuple[str, ...]) -> re.Pattern[str]:
     alternation = "|".join(
         r"\s+".join(re.escape(part) for part in cue.split())