diff --git a/CHANGELOG.md b/CHANGELOG.md
index d1d3fc5..41be77c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,7 @@ These breaking changes apply to Python JSONPath in its default configuration. We
 
 - Added the `startswith(value, prefix)` function extension. `startswith` returns `True` if both arguments are strings and the second argument is a prefix of the first argument. See the [filter functions](https://jg-rp.github.io/python-jsonpath/functions/#startswith) documentation.
 - The non-standard `keys()` function extension has been reimplemented. It used to be a simple Python function, `jsonpath.function_extensions.keys`. Now it is a "well-typed" class, `jsonpath.function_extensions.Keys`. See the [filter functions](https://jg-rp.github.io/python-jsonpath/functions/#keys) documentation.
+- Added `cache_capacity`, `debug` and `thread_safe` arguments to `jsonpath.function_extensions.Match` and `jsonpath.function_extensions.Search` constructors.
 
 **JSONPath features**
 
diff --git a/jsonpath/function_extensions/_pattern.py b/jsonpath/function_extensions/_pattern.py
index a42a689..d505f29 100644
--- a/jsonpath/function_extensions/_pattern.py
+++ b/jsonpath/function_extensions/_pattern.py
@@ -1,7 +1,88 @@
 from typing import List
+from typing import Optional
+
+try:
+    import regex as re
+
+    REGEX_AVAILABLE = True
+except ImportError:
+    import re  # type: ignore
+
+    REGEX_AVAILABLE = False
+
+try:
+    from iregexp_check import check
+
+    IREGEXP_AVAILABLE = True
+except ImportError:
+    IREGEXP_AVAILABLE = False
+
+from jsonpath.exceptions import JSONPathError
+from jsonpath.function_extensions import ExpressionType
+from jsonpath.function_extensions import FilterFunction
+from jsonpath.lru_cache import LRUCache
+from jsonpath.lru_cache import ThreadSafeLRUCache
+
+
+class AbstractRegexFilterFunction(FilterFunction):
+    """Base class for filter function that accept regular expression arguments.
+
+    Arguments:
+        cache_capacity: The size of the regular expression cache.
+        debug: When `True`, raise an exception when regex pattern compilation
+            fails. The default - as required by RFC 9535 - is `False`, which
+            silently ignores bad patterns.
+        thread_safe: When `True`, use a `ThreadSafeLRUCache` instead of an
+            instance of `LRUCache`.
+    """
+
+    arg_types = [ExpressionType.VALUE, ExpressionType.VALUE]
+    return_type = ExpressionType.LOGICAL
+
+    def __init__(
+        self,
+        *,
+        cache_capacity: int = 300,
+        debug: bool = False,
+        thread_safe: bool = False,
+    ):
+        self.cache: LRUCache[str, Optional[re.Pattern]] = (  # type: ignore
+            ThreadSafeLRUCache(capacity=cache_capacity)
+            if thread_safe
+            else LRUCache(capacity=cache_capacity)
+        )
+
+        self.debug = debug
+
+    def check_cache(self, pattern: str) -> Optional[re.Pattern]:  # type: ignore
+        """Return a compiled re pattern if `pattern` is valid, or `None` otherwise."""
+        try:
+            _pattern = self.cache[pattern]
+        except KeyError:
+            if IREGEXP_AVAILABLE and not check(pattern):
+                if self.debug:
+                    raise JSONPathError(
+                        "search pattern is not a valid I-Regexp", token=None
+                    ) from None
+                _pattern = None
+            else:
+                if REGEX_AVAILABLE:
+                    pattern = map_re(pattern)
+
+                try:
+                    _pattern = re.compile(pattern)
+                except re.error:
+                    if self.debug:
+                        raise
+                    _pattern = None
+
+            self.cache[pattern] = _pattern
+
+        return _pattern
 
 
 def map_re(pattern: str) -> str:
+    """Convert an I-Regexp pattern into a Python re pattern."""
     escaped = False
     char_class = False
     parts: List[str] = []
diff --git a/jsonpath/function_extensions/match.py b/jsonpath/function_extensions/match.py
index 68494b8..1743c3c 100644
--- a/jsonpath/function_extensions/match.py
+++ b/jsonpath/function_extensions/match.py
@@ -1,50 +1,19 @@
 """The standard `match` function extension."""
 
-try:
-    import regex as re
+from ._pattern import AbstractRegexFilterFunction
 
-    REGEX_AVAILABLE = True
-except ImportError:
-    import re  # type: ignore
 
-    REGEX_AVAILABLE = False
+class Match(AbstractRegexFilterFunction):
+    """The standard `match` function."""
 
-try:
-    from iregexp_check import check
-
-    IREGEXP_AVAILABLE = True
-except ImportError:
-    IREGEXP_AVAILABLE = False
-
-from jsonpath.function_extensions import ExpressionType
-from jsonpath.function_extensions import FilterFunction
-
-from ._pattern import map_re
-
-
-class Match(FilterFunction):
-    """A type-aware implementation of the standard `match` function."""
-
-    arg_types = [ExpressionType.VALUE, ExpressionType.VALUE]
-    return_type = ExpressionType.LOGICAL
-
-    def __call__(self, string: str, pattern: str) -> bool:
-        """Return `True` if _string_ matches _pattern_, or `False` otherwise."""
-        # TODO: re.match caches compiled patterns internally, but `map_re` and `check`
-        # are not cached.
-
-        # TODO: validate literal patterns ar compile time?
-
-        if IREGEXP_AVAILABLE and (not isinstance(pattern, str) or not check(pattern)):
+    def __call__(self, value: object, pattern: object) -> bool:
+        """Return `True` if _value_ matches _pattern_, or `False` otherwise."""
+        if not isinstance(value, str) or not isinstance(pattern, str):
             return False
 
-        if REGEX_AVAILABLE:
-            try:
-                pattern = map_re(pattern)
-            except TypeError:
-                return False
+        _pattern = self.check_cache(pattern)
 
-        try:
-            return bool(re.fullmatch(pattern, string))
-        except (TypeError, re.error):
+        if _pattern is None:
             return False
+
+        return bool(_pattern.fullmatch(value))
diff --git a/jsonpath/function_extensions/search.py b/jsonpath/function_extensions/search.py
index e6d9086..4ae2740 100644
--- a/jsonpath/function_extensions/search.py
+++ b/jsonpath/function_extensions/search.py
@@ -1,50 +1,19 @@
 """The standard `search` function extension."""
 
-try:
-    import regex as re
+from ._pattern import AbstractRegexFilterFunction
 
-    REGEX_AVAILABLE = True
-except ImportError:
-    import re  # type: ignore
 
-    REGEX_AVAILABLE = False
+class Search(AbstractRegexFilterFunction):
+    """The standard `search` function."""
 
-try:
-    from iregexp_check import check
-
-    IREGEXP_AVAILABLE = True
-except ImportError:
-    IREGEXP_AVAILABLE = False
-
-from jsonpath.function_extensions import ExpressionType
-from jsonpath.function_extensions import FilterFunction
-
-from ._pattern import map_re
-
-
-class Search(FilterFunction):
-    """A type-aware implementation of the standard `search` function."""
-
-    arg_types = [ExpressionType.VALUE, ExpressionType.VALUE]
-    return_type = ExpressionType.LOGICAL
-
-    def __call__(self, string: str, pattern: str) -> bool:
-        """Return `True` if _string_ contains _pattern_, or `False` otherwise."""
-        # TODO: re.search caches compiled patterns internally, but `map_re` and `check`
-        # are not cached.
-
-        # TODO: validate literal patterns ar compile time?
-
-        if IREGEXP_AVAILABLE and (not isinstance(pattern, str) or not check(pattern)):
+    def __call__(self, value: object, pattern: object) -> bool:
+        """Return `True` if _value_ matches _pattern_, or `False` otherwise."""
+        if not isinstance(value, str) or not isinstance(pattern, str):
             return False
 
-        if REGEX_AVAILABLE:
-            try:
-                pattern = map_re(pattern)
-            except TypeError:
-                return False
+        _pattern = self.check_cache(pattern)
 
-        try:
-            return bool(re.search(pattern, string))
-        except (TypeError, re.error):
+        if _pattern is None:
             return False
+
+        return bool(_pattern.search(value))
diff --git a/jsonpath/lru_cache.py b/jsonpath/lru_cache.py
new file mode 100644
index 0000000..86a43c0
--- /dev/null
+++ b/jsonpath/lru_cache.py
@@ -0,0 +1,130 @@
+"""An LRU cache with a mapping interface implemented using an ordered dict."""
+
+from collections import OrderedDict
+from threading import Lock
+from typing import Generic
+from typing import Iterator
+from typing import Optional
+from typing import Tuple
+from typing import TypeVar
+from typing import Union
+from typing import overload
+
+_KT = TypeVar("_KT")
+_VT = TypeVar("_VT")
+_T = TypeVar("_T")
+
+
+class LRUCache(Generic[_KT, _VT]):
+    """An LRU cache with a mapping interface."""
+
+    def __init__(self, capacity: int):
+        if capacity < 1:
+            raise ValueError("cache capacity must be greater than zero")
+
+        self.capacity = capacity
+        self._cache: OrderedDict[_KT, _VT] = OrderedDict()
+
+    def __getitem__(self, key: _KT) -> _VT:
+        value = self._cache[key]  # This will raise a KeyError if key is not cached
+        self._cache.move_to_end(key)
+        return value
+
+    def __setitem__(self, key: _KT, value: _VT) -> None:
+        try:
+            self._cache.move_to_end(key)
+        except KeyError:
+            if len(self._cache) >= self.capacity:
+                self._cache.popitem(last=False)
+
+        self._cache[key] = value
+
+    def __delitem__(self, key: _KT) -> None:
+        del self._cache[key]
+
+    def __len__(self) -> int:
+        return len(self._cache)
+
+    def __iter__(self) -> Iterator[_KT]:
+        return reversed(self._cache)
+
+    def __contains__(self, key: _KT) -> bool:
+        return key in self._cache
+
+    @overload
+    def get(self, key: _KT) -> Optional[_VT]: ...
+    @overload
+    def get(self, key: _KT, default: _VT) -> _VT: ...
+    @overload
+    def get(self, key: _KT, default: _T) -> Union[_VT, _T]: ...
+    def get(self, key: _KT, default: object = None) -> object:
+        """Return the cached value for _key_ if _key_ is in the cache, else default."""
+        try:
+            return self[key]
+        except KeyError:
+            return default
+
+    def keys(self) -> Iterator[_KT]:
+        """Return an iterator over this cache's keys."""
+        return reversed(self._cache.keys())
+
+    def values(self) -> Iterator[_VT]:
+        """Return an iterator over this cache's values."""
+        return reversed(self._cache.values())
+
+    def items(self) -> Iterator[Tuple[_KT, _VT]]:
+        """Return an iterator over this cache's key/value pairs."""
+        return reversed(self._cache.items())
+
+
+class ThreadSafeLRUCache(LRUCache[_KT, _VT]):
+    """A thread safe LRU cache."""
+
+    def __init__(self, capacity: int):
+        super().__init__(capacity)
+        self._lock = Lock()
+
+    def __getitem__(self, key: _KT) -> _VT:
+        with self._lock:
+            return super().__getitem__(key)
+
+    def __setitem__(self, key: _KT, value: _VT) -> None:
+        with self._lock:
+            return super().__setitem__(key, value)
+
+    def __delitem__(self, key: _KT) -> None:
+        with self._lock:
+            return super().__delitem__(key)
+
+    def __contains__(self, key: _KT) -> bool:
+        with self._lock:
+            return super().__contains__(key)
+
+    @overload
+    def get(self, key: _KT) -> Optional[_VT]: ...
+    @overload
+    def get(self, key: _KT, default: _VT) -> _VT: ...
+    @overload
+    def get(self, key: _KT, default: _T) -> Union[_VT, _T]: ...
+    def get(self, key: _KT, default: object = None) -> object:
+        """Return the cached value for _key_ if _key_ is in the cache, else default."""
+        # NOTE: self.__getitem__ is already acquiring the lock.
+        try:
+            return self[key]
+        except KeyError:
+            return default
+
+    def keys(self) -> Iterator[_KT]:
+        """Return an iterator over this cache's keys."""
+        with self._lock:
+            return super().keys()
+
+    def values(self) -> Iterator[_VT]:
+        """Return an iterator over this cache's values."""
+        with self._lock:
+            return super().values()
+
+    def items(self) -> Iterator[Tuple[_KT, _VT]]:
+        """Return an iterator over this cache's key/value pairs."""
+        with self._lock:
+            return super().items()
diff --git a/pyproject.toml b/pyproject.toml
index ca89351..0696765 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -59,8 +59,14 @@ dependencies = [
 ]
 
 [tool.hatch.envs.default.scripts]
-cov = "pytest --cov-report=term-missing --cov-config=pyproject.toml --cov=jsonpath --cov=tests {args}"
-cov-html = "pytest --cov-report=html --cov-config=pyproject.toml --cov=jsonpath --cov=tests {args}"
+cov = [
+  "hatch run no-regex:cov",
+  "pytest --cov-append --cov-report=term-missing --cov-config=pyproject.toml --cov=jsonpath --cov=tests {args}"
+]
+cov-html = [
+  "hatch run no-regex:cov",
+  "pytest --cov-append --cov-report=html --cov-config=pyproject.toml --cov=jsonpath --cov=tests {args}",
+]
 no-cov = "cov --no-cov {args}"
 test = "pytest {args}"
 lint = "ruff check ."
@@ -80,7 +86,11 @@ build = "mkdocs build --clean --strict"
 serve = "mkdocs serve --dev-addr localhost:8000"
 
 [tool.hatch.envs.no-regex]
-dependencies = ["pytest"]
+dependencies = ["pytest", "pytest-cov"]
+
+[tool.hatch.envs.no-regex.scripts]
+cov = "pytest --cov-report=term-missing --cov-config=pyproject.toml --cov=jsonpath --cov=tests tests/test_compliance.py {args}"
+
 
 [tool.coverage.run]
 branch = true
diff --git a/tests/test_regex_cache.py b/tests/test_regex_cache.py
new file mode 100644
index 0000000..c41eedb
--- /dev/null
+++ b/tests/test_regex_cache.py
@@ -0,0 +1,66 @@
+try:
+    import regex as re
+
+    REGEX_AVAILABLE = True
+except ImportError:
+    import re  # type: ignore
+
+    REGEX_AVAILABLE = False
+
+try:
+    import iregexp_check  # noqa: F401
+
+    IREGEXP_AVAILABLE = True
+except ImportError:
+    IREGEXP_AVAILABLE = False
+
+import pytest
+
+from jsonpath import JSONPathError
+from jsonpath.function_extensions import Search
+
+
+def test_patterns_are_cached() -> None:
+    search_func = Search(cache_capacity=2)
+    assert len(search_func.cache) == 0
+    assert search_func("abcdef", "bc.")
+    assert len(search_func.cache) == 1
+
+
+def test_malformed_patterns_are_cached() -> None:
+    search_func = Search(cache_capacity=2)
+    assert len(search_func.cache) == 0
+    assert search_func("abcdef", "bc[") is False
+    assert len(search_func.cache) == 1
+    assert search_func.cache["bc["] is None
+
+
+@pytest.mark.skipif(IREGEXP_AVAILABLE is False, reason="requires iregexp_check")
+def test_invalid_iregexp_patterns_are_cached() -> None:
+    search_func = Search(cache_capacity=2)
+    assert len(search_func.cache) == 0
+    assert search_func("ab123cdef", "\\d+") is False
+    assert len(search_func.cache) == 1
+    assert search_func.cache["\\d+"] is None
+
+
+def test_debug_regex_patterns() -> None:
+    search_func = Search(cache_capacity=2, debug=True)
+    assert len(search_func.cache) == 0
+
+    with pytest.raises((JSONPathError, re.error)):
+        search_func("abcdef", "bc[")
+
+
+def test_cache_capacity() -> None:
+    search_func = Search(cache_capacity=2)
+    assert len(search_func.cache) == 0
+    assert search_func("1abcdef", "ab[a-z]")
+    assert len(search_func.cache) == 1
+    assert search_func("2abcdef", "bc[a-z]")
+    assert len(search_func.cache) == 2  # noqa: PLR2004
+    assert search_func("3abcdef", "cd[a-z]")
+    assert len(search_func.cache) == 2  # noqa: PLR2004
+    assert "cd[a-z]" in search_func.cache
+    assert "bc[a-z]" in search_func.cache
+    assert "ab[a-z]" not in search_func.cache