diff --git a/src/llama-grammar.cpp b/src/llama-grammar.cpp
index 2d55070cec..c8eed1c053 100644
--- a/src/llama-grammar.cpp
+++ b/src/llama-grammar.cpp
@@ -9,7 +9,10 @@
 #include <cstdint>
 #include <stdexcept>
 
+#include <unordered_set>
+
 #define MAX_REPETITION_THRESHOLD 2000
+#define MAX_GRAMMAR_RECURSION_DEPTH 2000
 //
 // helpers
 //
@@ -825,12 +828,32 @@ static bool llama_grammar_match_token(
     return false;
 }
 
+// Hash function for llama_grammar_stack to enable std::unordered_set usage
+struct llama_grammar_stack_hash {
+    std::size_t operator()(const llama_grammar_stack & stack) const {
+        std::size_t hash = 0;
+        for (const auto * elem : stack) {
+            hash ^= std::hash<const void*>{}(elem) + 0x9e3779b9 + (hash << 6) + (hash >> 2);
+        }
+        return hash;
+    }
+};
+
 // transforms a grammar pushdown stack into N possible stacks, all ending
 // at a character range (terminal element)
 static void llama_grammar_advance_stack(
         const llama_grammar_rules  & rules,
         const llama_grammar_stack  & stack,
-              llama_grammar_stacks & new_stacks) {
+              llama_grammar_stacks & new_stacks,
+        std::unordered_set<llama_grammar_stack, llama_grammar_stack_hash> & history) {
+    if (history.size() >= MAX_GRAMMAR_RECURSION_DEPTH) {
+        return;
+    }
+
+    if (history.count(stack) > 0) {
+        return;
+    }
+
     if (stack.empty()) {
         if (std::find(new_stacks.begin(), new_stacks.end(), stack) == new_stacks.end()) {
             new_stacks.emplace_back(stack);
@@ -855,7 +878,9 @@ static void llama_grammar_advance_stack(
                     // if alternate is nonempty, add to stack
                     new_stack.push_back(subpos);
                 }
-                llama_grammar_advance_stack(rules, new_stack, new_stacks);
+                history.insert(stack);
+                llama_grammar_advance_stack(rules, new_stack, new_stacks, history);
+                history.erase(stack);
                 while (!llama_grammar_is_end_of_sequence(subpos)) {
                     // scan to end of alternate def
                     subpos++;
@@ -887,6 +912,14 @@ static void llama_grammar_advance_stack(
     }
 }
 
+static void llama_grammar_advance_stack(
+        const llama_grammar_rules  & rules,
+        const llama_grammar_stack  & stack,
+              llama_grammar_stacks & new_stacks) {
+    std::unordered_set<llama_grammar_stack, llama_grammar_stack_hash> history;
+    llama_grammar_advance_stack(rules, stack, new_stacks, history);
+}
+
 static llama_grammar_candidates llama_grammar_reject_candidates(
         const llama_grammar_rules      & rules,
         const llama_grammar_stacks     & stacks,
diff --git a/tests/test-grammar-integration.cpp b/tests/test-grammar-integration.cpp
index 7aa7e58a5c..f8b3a028db 100644
--- a/tests/test-grammar-integration.cpp
+++ b/tests/test-grammar-integration.cpp
@@ -784,6 +784,23 @@ static void test_quantifiers() {
             "0xFF 0x12 0xAB 0x00 0x00 0x00",
         }
     );
+    test_grammar(
+        "nested repetition",
+        // Grammar
+        R"""(root ::= ("a"* )*)""",
+        // Passing strings
+        {
+            "",
+            "a",
+            "aa",
+            "aaa",
+        },
+        // Failing strings
+        {
+            "b",
+            "ab",
+        }
+    );
 }
 
 static void test_failure_missing_root() {