diff --git a/docs/lexicon.html b/docs/lexicon.html
index 49ee4c266..7a2ecf710 100644
--- a/docs/lexicon.html
+++ b/docs/lexicon.html
@@ -509,6 +509,15 @@ <h3 class="title-3">
           - returns a copy of this string converted to lowercase.
         </span>
       </li>
+      <li>
+        <span>
+          <code class="code"
+            ><span class="fn-name">matches</span><span class="fn-p">(</span
+            ><span class="fn-arg">pattern</span><span class="fn-p">)</span></code
+          >
+          - returns true if the string matches the regular expression given by <code class="code">pattern</code>.
+        </span>
+      </li>
     </ul>
   </section>
 
diff --git a/rules/builtins.build_defs b/rules/builtins.build_defs
index f405bff5b..1f62089b0 100644
--- a/rules/builtins.build_defs
+++ b/rules/builtins.build_defs
@@ -109,6 +109,8 @@ def upper(self:str) -> str:
     pass
 def lower(self:str) -> str:
     pass
+def matches(self:str, pattern: str) -> bool:
+    pass
 
 def fail(msg:str):
     pass
diff --git a/src/parse/asp/builtins.go b/src/parse/asp/builtins.go
index d17cd7b2b..353478b07 100644
--- a/src/parse/asp/builtins.go
+++ b/src/parse/asp/builtins.go
@@ -7,6 +7,7 @@ import (
 	"io"
 	"path/filepath"
 	"reflect"
+	"regexp"
 	"slices"
 	"sort"
 	"strconv"
@@ -98,6 +99,7 @@ func registerBuiltins(s *scope) {
 		"count":        setNativeCode(s, "count", strCount),
 		"upper":        setNativeCode(s, "upper", strUpper),
 		"lower":        setNativeCode(s, "lower", strLower),
+		"matches":      setNativeCode(s, "matches", strMatches),
 	}
 	s.interpreter.stringMethods["format"].kwargs = true
 	s.interpreter.dictMethods = map[string]*pyFunc{
@@ -645,6 +647,20 @@ func strLower(s *scope, args []pyObject) pyObject {
 	return pyString(strings.ToLower(self))
 }
 
+func strMatches(s *scope, args []pyObject) pyObject {
+	self := string(args[0].(pyString))
+	pattern := string(args[1].(pyString))
+	compiledRegex := s.interpreter.regexCache.Get(pattern)
+	if compiledRegex == nil {
+		compiled, err := regexp.Compile(pattern)
+		s.Assert(err == nil, "%s", err)
+		// We don't need to check if another task inserted the regex first, as it will be an identical result.
+		s.interpreter.regexCache.Add(pattern, compiled)
+		compiledRegex = compiled
+	}
+	return newPyBool(compiledRegex.MatchString(self))
+}
+
 func boolType(s *scope, args []pyObject) pyObject {
 	return newPyBool(args[0].IsTruthy())
 }
diff --git a/src/parse/asp/interpreter.go b/src/parse/asp/interpreter.go
index 4d8199439..93e4ca0a3 100644
--- a/src/parse/asp/interpreter.go
+++ b/src/parse/asp/interpreter.go
@@ -6,6 +6,7 @@ import (
 	"iter"
 	"path/filepath"
 	"reflect"
+	"regexp"
 	"runtime/debug"
 	"runtime/pprof"
 	"strings"
@@ -31,6 +32,8 @@ type interpreter struct {
 	limiter         semaphore
 
 	stringMethods, dictMethods, configMethods map[string]*pyFunc
+
+	regexCache *cmap.Map[string, *regexp.Regexp]
 }
 
 // newInterpreter creates and returns a new interpreter instance.
@@ -42,10 +45,11 @@ func newInterpreter(state *core.BuildState, p *Parser) *interpreter {
 		locals: map[string]pyObject{},
 	}
 	i := &interpreter{
-		scope:   s,
-		parser:  p,
-		configs: map[*core.BuildState]*pyConfig{},
-		limiter: make(semaphore, state.Config.Parse.NumThreads),
+		scope:      s,
+		parser:     p,
+		configs:    map[*core.BuildState]*pyConfig{},
+		limiter:    make(semaphore, state.Config.Parse.NumThreads),
+		regexCache: cmap.New[string, *regexp.Regexp](cmap.SmallShardCount, cmap.XXHash),
 	}
 	// If we're creating an interpreter for a subrepo, we should share the subinclude cache.
 	if p.interpreter != nil {
diff --git a/test/builtins/BUILD b/test/builtins/BUILD
new file mode 100644
index 000000000..ccb21ec42
--- /dev/null
+++ b/test/builtins/BUILD
@@ -0,0 +1,7 @@
+subinclude("//test/build_defs")
+
+please_repo_e2e_test(
+    name = "strings_test",
+    plz_command = "plz build",
+    repo = "strings",
+)
diff --git a/test/builtins/strings/.plzconfig b/test/builtins/strings/.plzconfig
new file mode 100644
index 000000000..ea85e4f73
--- /dev/null
+++ b/test/builtins/strings/.plzconfig
@@ -0,0 +1,2 @@
+[parse]
+BuildFileName = BUILD_FILE
diff --git a/test/builtins/strings/BUILD_FILE b/test/builtins/strings/BUILD_FILE
new file mode 100644
index 000000000..8d7275107
--- /dev/null
+++ b/test/builtins/strings/BUILD_FILE
@@ -0,0 +1,45 @@
+
+assert ",".join(["a","b","c"]) == "a,b,c"
+
+assert "a,b,c".split(",") == ["a", "b", "c"]
+
+assert "abc".replace("bc", "ab") == "aab"
+
+pre, sep, post = "a,b,c".partition(",")
+assert pre == "a" and sep == "," and post == "b,c"
+
+pre, sep, post = "a,b,c".rpartition(",")
+assert pre == "a,b" and sep == "," and post == "c"
+
+assert "abc".startswith("ab") == True
+
+assert "abc".endswith("bc") == True
+
+assert "a{var1},b{var2},c{var3}".format(var1="a", var2=2, var3=[3]) == "aa,b2,c[3]"
+
+assert "abcba".lstrip("a") == "bcba"
+
+assert "abcba".rstrip("a") == "abcb"
+
+assert "abcba".strip("a") == "bcb"
+
+assert "abc".removeprefix("ab") == "c"
+
+assert "abc".removesuffix("bc") == "a"
+
+assert "abcba".find("b") == 1
+
+assert "abcba".rfind("b") == 3
+
+assert "abcba".count("b") == 2
+
+assert "abc".upper() == "ABC"
+
+assert "ABC".lower() == "abc"
+
+
+assert "abc".matches("a.c")
+
+assert "abbbbbbc".matches("a.*c")
+
+assert not "abc".matches("$b")