diff --git a/security/R-cran-openssl/Makefile b/security/R-cran-openssl/Makefile
index 5a5bf5694d44..151cfdffebdb 100644
--- a/security/R-cran-openssl/Makefile
+++ b/security/R-cran-openssl/Makefile
@@ -1,22 +1,22 @@
 # Created by: TAKATSU Tomonari <tota@FreeBSD.org>
 
 PORTNAME=	openssl
-PORTVERSION=	1.4.3
+PORTVERSION=	1.4.4
 CATEGORIES=	security
 DISTNAME=	${PORTNAME}_${PORTVERSION}
 
 MAINTAINER=	tota@FreeBSD.org
 COMMENT=	Toolkit for Encryption, Signatures and Certificates Based on OpenSSL
 
 LICENSE=	MIT
 
 CRAN_DEPENDS=	R-cran-askpass>0:security/R-cran-askpass
 BUILD_DEPENDS=	bash:shells/bash \
 		${CRAN_DEPENDS}
 RUN_DEPENDS=	${CRAN_DEPENDS}
 
 USES=		cran:auto-plist,compiles shebangfix ssl
 
 SHEBANG_FILES=	${WRKSRC}/tests/google.dk/generate.bash
 
 .include <bsd.port.mk>
diff --git a/security/R-cran-openssl/distinfo b/security/R-cran-openssl/distinfo
index e1c5adf70101..3e7a8e3dedd4 100644
--- a/security/R-cran-openssl/distinfo
+++ b/security/R-cran-openssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1600779702
-SHA256 (openssl_1.4.3.tar.gz) = 342001df8ecff5df2cdf757f123d35ea4b449751045f708b91f27c1be0d48269
-SIZE (openssl_1.4.3.tar.gz) = 1207708
+TIMESTAMP = 1619971716
+SHA256 (openssl_1.4.4.tar.gz) = 920fb4494da6cf78b55937a9f645d11dae4d7982afa640f28c1be74d486cc874
+SIZE (openssl_1.4.4.tar.gz) = 1311285