diff --git a/CHANGELOG.md b/CHANGELOG.md
index e4248371..afd8e204 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,8 @@
 # Unreleased
 
+* Better check `freeze` option support in JSON compile cache.
+  Previously `JSON.load_file(..., freeze: true)` would be cached even when the msgpack version is missing support for it.
+
 # 1.10.1
 
 * Fix `Kernel#autoload`'s fallback path always being executed.
diff --git a/lib/bootsnap/compile_cache/json.rb b/lib/bootsnap/compile_cache/json.rb
index 7f81152c..143f826a 100644
--- a/lib/bootsnap/compile_cache/json.rb
+++ b/lib/bootsnap/compile_cache/json.rb
@@ -52,7 +52,9 @@ def init!
           self.msgpack_factory = MessagePack::Factory.new
           self.supported_options = [:symbolize_names]
           if ::JSON.parse('["foo"]', freeze: true).first.frozen?
-            self.supported_options = [:freeze]
+            if MessagePack.load(MessagePack.dump("foo"), freeze: true).frozen?
+              self.supported_options = [:freeze]
+            end
           end
           supported_options.freeze
         end