diff --git a/security/rubygem-openssl/Makefile b/security/rubygem-openssl/Makefile
index 1756243c075a..bf4a0ed7825a 100644
--- a/security/rubygem-openssl/Makefile
+++ b/security/rubygem-openssl/Makefile
@@ -1,5 +1,5 @@
 PORTNAME=	openssl
-PORTVERSION=	3.2.0
+PORTVERSION=	3.3.0
 CATEGORIES=	security rubygems
 MASTER_SITES=	RG
 
@@ -10,7 +10,7 @@ WWW=		https://github.com/ruby/openssl
 LICENSE=	BSD2CLAUSE RUBY
 LICENSE_COMB=	dual
 LICENSE_FILE_BSD2CLAUSE=${WRKSRC}/BSDL
-LICENSE_FILE_RUBY=	${WRKSRC}/LICENSE.txt
+LICENSE_FILE_RUBY=	${WRKSRC}/COPYING
 
 USES=		cpe gem ssl
 
diff --git a/security/rubygem-openssl/distinfo b/security/rubygem-openssl/distinfo
index a39d74e1de79..172cb0d65bc6 100644
--- a/security/rubygem-openssl/distinfo
+++ b/security/rubygem-openssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1695588874
-SHA256 (rubygem/openssl-3.2.0.gem) = 3c4bb8760977b4becd2819c6c2569bcf5c6f48b32b9f7a4ce1fd37f996378d14
-SIZE (rubygem/openssl-3.2.0.gem) = 203264
+TIMESTAMP = 1735228172
+SHA256 (rubygem/openssl-3.3.0.gem) = ff3a573fc97ab30f69483fddc80029f91669bf36532859bd182d1836f45aee79
+SIZE (rubygem/openssl-3.3.0.gem) = 207872