Index: head/Mk/bsd.openssl.mk
===================================================================
--- head/Mk/bsd.openssl.mk
+++ head/Mk/bsd.openssl.mk
@@ -107,7 +107,7 @@
 
 # try to guess SHLIBVER for libressl
 .if defined(OPENSSL_PORT) && ${OPENSSL_PORT} == security/libressl
-OPENSSL_SHLIBVER?=	33
+OPENSSL_SHLIBVER?=	34
 .endif
 
 # default
Index: head/UPDATING
===================================================================
--- head/UPDATING
+++ head/UPDATING
@@ -5,6 +5,21 @@
 You should get into the habit of checking this file for changes each time
 you update your ports collection, before attempting any port upgrades.
 
+20150708:
+  AFFECTS: users of security/libressl
+  AUTHOR: brnrd@FreeBSD.org
+
+  After upgrading to 2.2.1, manually update all packages that depend on
+  any of the libraries provided by LibreSSL (libssl, libcrypto and
+  libtls) since the versions of these libraries have changed. Normally,
+  you can obtain the list of dependent software by running the following
+  command:
+
+  pkg query -e '%n = libressl' %ro
+
+  Then you should rebuild all ports depending on libressl to avoid dangling
+  shared library dependencies.
+
 20150707:
   AFFECTS: users of net-mgmt/netmagis-*
   AUTHOR: pgollucci@FreeBSD.org
Index: head/security/libressl/Makefile
===================================================================
--- head/security/libressl/Makefile
+++ head/security/libressl/Makefile
@@ -2,7 +2,7 @@
 # $FreeBSD$
 
 PORTNAME=	libressl
-PORTVERSION=	2.2.0
+PORTVERSION=	2.2.1
 CATEGORIES=	security devel
 MASTER_SITES=	OPENBSD/LibreSSL
 
Index: head/security/libressl/distinfo
===================================================================
--- head/security/libressl/distinfo
+++ head/security/libressl/distinfo
@@ -1,2 +1,2 @@
-SHA256 (libressl-2.2.0.tar.gz) = 9690d8f38a5d48425395452eeb305b05bb0f560cd96e0ee30f370d4f16563040
-SIZE (libressl-2.2.0.tar.gz) = 2862547
+SHA256 (libressl-2.2.1.tar.gz) = 4f331750abfc3b605b02eeca1e8994fa0d2629985bc3f62924378197fbfe572d
+SIZE (libressl-2.2.1.tar.gz) = 2855917
Index: head/security/libressl/files/patch-include_openssl_opensslv.h
===================================================================
--- head/security/libressl/files/patch-include_openssl_opensslv.h
+++ head/security/libressl/files/patch-include_openssl_opensslv.h
@@ -6,6 +6,6 @@
  #define LIBRESSL_VERSION_NUMBER	0x20000000L
 -#define OPENSSL_VERSION_NUMBER	0x20000000L
 +#define OPENSSL_VERSION_NUMBER	0x1000107fL
- #define OPENSSL_VERSION_TEXT	"LibreSSL 2.2.0"
+ #define OPENSSL_VERSION_TEXT	"LibreSSL 2.2.1"
  #define OPENSSL_VERSION_PTEXT	" part of " OPENSSL_VERSION_TEXT
  
Index: head/security/libressl/pkg-plist
===================================================================
--- head/security/libressl/pkg-plist
+++ head/security/libressl/pkg-plist
@@ -74,16 +74,16 @@
 include/tls.h
 lib/libcrypto.a
 lib/libcrypto.so
-lib/libcrypto.so.33
-lib/libcrypto.so.33.0.0
+lib/libcrypto.so.34
+lib/libcrypto.so.34.0.0
 lib/libssl.a
 lib/libssl.so
-lib/libssl.so.32
-lib/libssl.so.32.0.0
+lib/libssl.so.33
+lib/libssl.so.33.0.0
 lib/libtls.a
 lib/libtls.so
-lib/libtls.so.3
-lib/libtls.so.3.0.1
+lib/libtls.so.4
+lib/libtls.so.4.0.0
 libdata/pkgconfig/libcrypto.pc
 libdata/pkgconfig/libssl.pc
 libdata/pkgconfig/libtls.pc