diff --git a/security/libressl-devel/Makefile b/security/libressl-devel/Makefile
index 8e0ee15bf31a..93ce326d69e5 100644
--- a/security/libressl-devel/Makefile
+++ b/security/libressl-devel/Makefile
@@ -2,7 +2,7 @@
 # $FreeBSD$
 
 PORTNAME=	libressl
-PORTVERSION=	2.5.1
+PORTVERSION=	2.5.2
 CATEGORIES=	security devel
 MASTER_SITES=	OPENBSD/LibreSSL
 PKGNAMESUFFIX=	-devel
diff --git a/security/libressl-devel/distinfo b/security/libressl-devel/distinfo
index 6e02eea1af1b..77880d220c8c 100644
--- a/security/libressl-devel/distinfo
+++ b/security/libressl-devel/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1485951332
-SHA256 (libressl-2.5.1.tar.gz) = f71ae0a824b78fb1a47ffa23c9c26e9d96c5c9b29234eacedce6b4c7740287cd
-SIZE (libressl-2.5.1.tar.gz) = 3266271
+TIMESTAMP = 1490549829
+SHA256 (libressl-2.5.2.tar.gz) = 0ffa7d70809284a4ac96e965918a61c1d7930bca865457a7db0ff0afc8201c82
+SIZE (libressl-2.5.2.tar.gz) = 3277320
diff --git a/security/libressl-devel/files/patch-apps_ocspcheck_http.c b/security/libressl-devel/files/patch-apps_ocspcheck_http.c
deleted file mode 100644
index f8dd9f7e1e4f..000000000000
--- a/security/libressl-devel/files/patch-apps_ocspcheck_http.c
+++ /dev/null
@@ -1,10 +0,0 @@
---- apps/ocspcheck/http.c.orig	2017-01-27 04:29:45 UTC
-+++ apps/ocspcheck/http.c
-@@ -18,6 +18,7 @@
- #include <sys/socket.h>
- #include <sys/param.h>
- #include <arpa/inet.h>
-+#include <netinet/in.h>
- 
- #include <ctype.h>
- #include <err.h>
diff --git a/security/libressl-devel/files/patch-apps_ocspcheck_ocspcheck.c b/security/libressl-devel/files/patch-apps_ocspcheck_ocspcheck.c
deleted file mode 100644
index 87149174ff1a..000000000000
--- a/security/libressl-devel/files/patch-apps_ocspcheck_ocspcheck.c
+++ /dev/null
@@ -1,20 +0,0 @@
---- apps/ocspcheck/ocspcheck.c.orig	2017-01-27 11:30:47 UTC
-+++ apps/ocspcheck/ocspcheck.c
-@@ -17,6 +17,7 @@
- #include <arpa/inet.h>
- #include <sys/socket.h>
- #include <sys/stat.h>
-+#include <netinet/in.h>
- 
- #include <err.h>
- #include <fcntl.h>
-@@ -76,7 +77,9 @@ host_dns(const char *s, struct addr vec[
- 	error = getaddrinfo(s, NULL, &hints, &res0);
- 
- 	if (error == EAI_AGAIN ||
-+#ifdef EAI_NODATA
- 	    error == EAI_NODATA ||
-+#endif
- 	    error == EAI_NONAME)
- 		return(0);
- 
diff --git a/security/libressl-devel/pkg-plist b/security/libressl-devel/pkg-plist
index 33a8ba3a5dda..14e71c2d615f 100644
--- a/security/libressl-devel/pkg-plist
+++ b/security/libressl-devel/pkg-plist
@@ -76,15 +76,15 @@ include/tls.h
 lib/libcrypto.a
 lib/libcrypto.so
 lib/libcrypto.so.41
-lib/libcrypto.so.41.0.0
+lib/libcrypto.so.41.0.1
 lib/libssl.a
 lib/libssl.so
 lib/libssl.so.43
-lib/libssl.so.43.0.1
+lib/libssl.so.43.0.2
 lib/libtls.a
 lib/libtls.so
 lib/libtls.so.15
-lib/libtls.so.15.0.3
+lib/libtls.so.15.0.4
 libdata/pkgconfig/libcrypto.pc
 libdata/pkgconfig/libssl.pc
 libdata/pkgconfig/libtls.pc
@@ -825,6 +825,7 @@ man/man1/openssl.1.gz
 %%MAN3%%man/man3/ERR_PACK.3.gz
 %%MAN3%%man/man3/ERR_add_error_data.3.gz
 %%MAN3%%man/man3/ERR_add_error_vdata.3.gz
+%%MAN3%%man/man3/ERR_asprintf_error_data.3.gz
 %%MAN3%%man/man3/ERR_clear_error.3.gz
 %%MAN3%%man/man3/ERR_error_string.3.gz
 %%MAN3%%man/man3/ERR_error_string_n.3.gz