diff --git a/prism/util/pm_integer.c b/prism/util/pm_integer.c
index ff683d3501..e39108a05b 100644
--- a/prism/util/pm_integer.c
+++ b/prism/util/pm_integer.c
@@ -159,16 +159,19 @@ pm_integer_memsize(const pm_integer_t *integer) {
  */
 int
 pm_integer_compare(const pm_integer_t *left, const pm_integer_t *right) {
-    if (left->length < right->length) return -1;
-    if (left->length > right->length) return 1;
+    if (left->negative != right->negative) return left->negative ? -1 : 1;
+    int negative = left->negative ? -1 : 1;
+
+    if (left->length < right->length) return -1 * negative;
+    if (left->length > right->length) return 1 * negative;
 
     for (
         const pm_integer_word_t *left_word = &left->head, *right_word = &right->head;
         left_word != NULL && right_word != NULL;
         left_word = left_word->next, right_word = right_word->next
     ) {
-        if (left_word->value < right_word->value) return -1;
-        if (left_word->value > right_word->value) return 1;
+        if (left_word->value < right_word->value) return -1 * negative;
+        if (left_word->value > right_word->value) return 1 * negative;
     }
 
     return 0;
diff --git a/test/prism/static_literals_test.rb b/test/prism/static_literals_test.rb
index b28f1f9187..6108e2ddbc 100644
--- a/test/prism/static_literals_test.rb
+++ b/test/prism/static_literals_test.rb
@@ -13,6 +13,10 @@ module Prism
       assert_warning((2**32).to_s(10), "0x#{(2**32).to_s(16)}")
       assert_warning((2**64).to_s(10), "0x#{(2**64).to_s(16)}")
 
+      refute_warning("1", "-1")
+      refute_warning((2**32).to_s(10), "-0x#{(2**32).to_s(16)}")
+      refute_warning((2**64).to_s(10), "-0x#{(2**64).to_s(16)}")
+
       assert_warning("__LINE__", "2")
       assert_warning("3", "__LINE__")
 
@@ -33,6 +37,7 @@ module Prism
       assert_warning("\"#{__FILE__}\"", "__FILE__")
 
       assert_warning("/foo/")
+
       refute_warning("/foo/", "/foo/i")
 
       assert_warning(":foo")