diff --git a/ext/openssl/ossl_pkey.c b/ext/openssl/ossl_pkey.c
index d2fd5b29c32204..a53332b17edf84 100644
--- a/ext/openssl/ossl_pkey.c
+++ b/ext/openssl/ossl_pkey.c
@@ -1496,8 +1496,10 @@ ossl_pkey_derive(int argc, VALUE *argv, VALUE self)
         EVP_PKEY_CTX_free(ctx);
         ossl_raise(ePKeyError, "EVP_PKEY_derive");
     }
-    if (keylen > LONG_MAX)
+    if (keylen > LONG_MAX) {
+        EVP_PKEY_CTX_free(ctx);
         rb_raise(ePKeyError, "derived key would be too large");
+    }
     str = ossl_str_new(NULL, (long)keylen, &state);
     if (state) {
         EVP_PKEY_CTX_free(ctx);
diff --git a/spec/bundler/realworld/fixtures/tapioca/Gemfile.lock b/spec/bundler/realworld/fixtures/tapioca/Gemfile.lock
index 4ce06de722cfaa..c2df2f92299ad2 100644
--- a/spec/bundler/realworld/fixtures/tapioca/Gemfile.lock
+++ b/spec/bundler/realworld/fixtures/tapioca/Gemfile.lock
@@ -32,7 +32,7 @@ GEM
       thor (>= 1.2.0)
       yard-sorbet
     thor (1.4.0)
-    yard (0.9.37)
+    yard (0.9.42)
     yard-sorbet (0.9.0)
       sorbet-runtime
       yard