diff --git a/security/py-openssl/Makefile b/security/py-openssl/Makefile
index c56244a49050d..87abb9a12754e 100644
--- a/security/py-openssl/Makefile
+++ b/security/py-openssl/Makefile
@@ -1,5 +1,5 @@
 PORTNAME=	openssl
-PORTVERSION=	20.0.1
+DISTVERSION=	21.0.0
 PORTEPOCH=	1
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
diff --git a/security/py-openssl/distinfo b/security/py-openssl/distinfo
index a13e9b15cf524..c2b3c91de7fc4 100644
--- a/security/py-openssl/distinfo
+++ b/security/py-openssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1648120923
-SHA256 (pyOpenSSL-20.0.1.tar.gz) = 4c231c759543ba02560fcd2480c48dcec4dae34c9da7d3747c508227e0624b51
-SIZE (pyOpenSSL-20.0.1.tar.gz) = 173736
+TIMESTAMP = 1673046083
+SHA256 (pyOpenSSL-21.0.0.tar.gz) = 5e2d8c5e46d0d865ae933bef5230090bdaf5506281e9eec60fa250ee80600cb3
+SIZE (pyOpenSSL-21.0.0.tar.gz) = 175652