diff --git a/irc/hexchat/Makefile b/irc/hexchat/Makefile
index ff518814c0de..d0ee55a51e40 100644
--- a/irc/hexchat/Makefile
+++ b/irc/hexchat/Makefile
@@ -1,90 +1,92 @@
 # Created by: Rusmir Dusko <nemysis@FreeBSD.org>
 
 PORTNAME=	hexchat
-PORTVERSION=	2.14.3
-PORTREVISION=	1
+PORTVERSION=	2.16.0
 DISTVERSIONPREFIX=	v
 CATEGORIES=	irc gnome
 
 MAINTAINER=	pkubaj@FreeBSD.org
 COMMENT=	IRC chat program with GTK and Text Frontend
 
 LICENSE=	GPLv2+
 LICENSE_FILE=	${WRKSRC}/COPYING
 
-BUILD_DEPENDS=	${LOCALBASE}/libdata/pkgconfig/iso-codes.pc:misc/iso-codes
+BUILD_DEPENDS=	${LOCALBASE}/libdata/pkgconfig/iso-codes.pc:misc/iso-codes \
+		${PYTHON_PKGNAMEPREFIX}cffi>0:devel/py-cffi@${PY_FLAVOR}
 LIB_DEPENDS=	libproxy.so:net/libproxy \
 		libfontconfig.so:x11-fonts/fontconfig \
 		libdbus-1.so:devel/dbus \
 		libfreetype.so:print/freetype2
 RUN_DEPENDS=	${LOCALBASE}/share/xml/iso-codes/iso_639.xml:misc/iso-codes
 
 USES=		compiler:c++11-lang desktop-file-utils gettext-tools gnome \
 		libtool localbase meson ninja pkgconfig python:3.5+ shebangfix \
 		ssl xorg
 USE_GNOME=	cairo gtk20 intltool libxml2
 USE_XORG=	x11
 USE_GITHUB=	yes
 
-MESON_ARGS=	-Dwith-ssl=true -Dwith-gtk=true -Dwith-python=python-${PYTHON_VER}
+MESON_ARGS=	-Dtls=enabled -Dgtk-frontend=true -Dwith-python=python-${PYTHON_VER}
 INSTALLS_ICONS=	yes
 INSTALL_TARGET=	install-strip
 
 LIBS+=		-lX11
 
 SUB_FILES=	pkg-message
 
 PORTDOCS=	*
 
-OPTIONS_DEFINE=		CA_BUNDLE CANBERRA DBUS DOCS FISHLIM LUA NOTIFY \
-			PERL TEXTFE SYSINFO
+OPTIONS_DEFINE=		CA_BUNDLE CANBERRA DBUS DOCS FISHLIM LUA PERL TEXTFE \
+			SYSINFO
 
 OPTIONS_DEFAULT=	CA_BUNDLE CANBERRA DBUS NOTIFY PERL
 
 OPTIONS_SUB=	yes
 
 CA_BUNDLE_DESC=		Include CA bundle for SSL verification
 CANBERRA_DESC=		Audio support via Libcanberra
 FISHLIM_DESC=		FiSHLiM plugin
 TEXTFE_DESC=		Text frontend
 SYSINFO_DESC=		Sysinfo plugin
 
 CA_BUNDLE_RUN_DEPENDS=	${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 CA_BUNDLE_VARS=	CA_BUNDLE="${LOCALBASE}/share/certs/ca-root-nss.crt"
 CA_BUNDLE_VARS_OFF=	CA_BUNDLE=NULL
 CANBERRA_LIB_DEPENDS=	libcanberra.so:audio/libcanberra
-CANBERRA_MESON_TRUE=	with-libcanberra
+CANBERRA_MESON_ON=	-Dlibcanberra=enabled
+CANBERRA_MESON_OFF=	-Dlibcanberra=disabled
 DBUS_LIB_DEPENDS=	libdbus-glib-1.so:devel/dbus-glib
-DBUS_MESON_TRUE=	with-dbus
+DBUS_MESON_ON=		-Ddbus=enabled
+DBUS_MESON_OFF=		-Ddbus=disabled
 FISHLIM_MESON_TRUE=	with-fishlim
 LUA_MESON_ON=		-Dwith-lua=lua-${LUA_VER}
 LUA_MESON_OFF=		-Dwith-lua=false
 LUA_USES=		lua
 LUA_USE=		GCC=any
 NOTIFY_LIB_DEPENDS=	libnotify.so:devel/libnotify
 NOTIFY_MESON_TRUE=	with-libnotify
 PERL_MESON_TRUE=	with-perl
 PERL_USES=		perl5
-TEXTFE_MESON_TRUE=	with-text
+TEXTFE_MESON_TRUE=	text-frontend
 SYSINFO_MESON_TRUE=	with-sysinfo
 
+BINARY_ALIAS=	python3=${PYTHON_CMD}
+
 SHEBANG_FILES=	meson_post_install.py \
 		plugins/perl/generate_header.py \
 		src/common/make-te.py
 
 post-patch:
-	@${REINPLACE_CMD} -e 's|%%CA_BUNDLE%%|${CA_BUNDLE}|' \
-		${WRKSRC}/src/common/server.c
 	@${REINPLACE_CMD} -e 's|%%PREFIX%%|${PREFIX}|g' \
 		-e 's|%%PERL_VER%%|${PERL_VER}|g' \
 		${WRKSRC}/plugins/perl/meson.build
 
 post-install:
 	${LN} -sf ../share/icons/hicolor/48x48/apps/${PORTNAME}.png \
 		${STAGEDIR}${PREFIX}/share/pixmaps/
 
 post-install-DOCS-on:
 	@${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_DATA} ${WRKSRC}/*.md ${STAGEDIR}${DOCSDIR}
 
 .include <bsd.port.mk>
diff --git a/irc/hexchat/distinfo b/irc/hexchat/distinfo
index e74990e9e733..98ce823099ff 100644
--- a/irc/hexchat/distinfo
+++ b/irc/hexchat/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1577021248
-SHA256 (hexchat-hexchat-v2.14.3_GH0.tar.gz) = 3e32b120a0fde6a3949cc9d2b87b00534e11c150b3249830736e7f86b050343a
-SIZE (hexchat-hexchat-v2.14.3_GH0.tar.gz) = 2759502
+TIMESTAMP = 1633136688
+SHA256 (hexchat-hexchat-v2.16.0_GH0.tar.gz) = 5c7f35317bb3bc437fc5fb57392ddc13ba11c173718cdfe4de89d69c30a40b06
+SIZE (hexchat-hexchat-v2.16.0_GH0.tar.gz) = 2769078
diff --git a/irc/hexchat/files/patch-meson.build b/irc/hexchat/files/patch-meson.build
index 80ac239f3c41..f953c239872b 100644
--- a/irc/hexchat/files/patch-meson.build
+++ b/irc/hexchat/files/patch-meson.build
@@ -1,44 +1,56 @@
---- meson.build.orig	2019-12-21 06:38:06 UTC
-+++ meson.build
-@@ -16,11 +16,21 @@ cc = meson.get_compiler('c')
+--- meson.build.orig	2021-10-01 21:52:09.000000000 +0200
++++ meson.build	2021-10-07 10:35:49.739120000 +0200
+@@ -15,7 +15,7 @@
+ 
  libgio_dep = dependency('gio-2.0', version: '>= 2.34.0')
  libgmodule_dep = dependency('gmodule-2.0')
- global_deps = []
+-
 +libssl_dep_found = false
- if cc.get_id() == 'msvc'
-   libssl_dep = cc.find_library('libeay32')
+ libcanberra_dep = dependency('libcanberra', version: '>= 0.22',
+                              required: get_option('libcanberra'))
+ dbus_glib_dep = dependency('dbus-glib-1', required: get_option('dbus'))
+@@ -25,7 +25,16 @@
+   libssl_dep = cc.find_library('libssl')
  else
    libssl_dep = dependency('openssl', version: '>= 0.9.8',
--                          required: get_option('with-ssl'))
+-                          required: get_option('tls'))
 +                          required: false)
 +  if not libssl_dep.found()
 +    libssl_dep = [
-+        cc.find_library('ssl', required: get_option('with-ssl')),
-+        cc.find_library('crypto', required: get_option('with-ssl'))
++        cc.find_library('ssl', required: get_option('tls')),
++        cc.find_library('crypto', required: get_option('tls'))
 +    ]
 +    libssl_dep_found = libssl_dep[0].found()
 +  else
 +    libssl_dep_found = libssl_dep.found()
 +  endif
  endif
  
  config_h = configuration_data()
-@@ -49,7 +59,7 @@ config_h.set('GLIB_VERSION_MIN_REQUIRED', 'GLIB_VERSIO
- config_h.set('HAVE_MEMRCHR', cc.has_function('memrchr'))
- config_h.set('HAVE_STRINGS_H', cc.has_header('strings.h'))
+@@ -37,7 +46,7 @@
+ config_h.set10('ENABLE_NLS', true)
+ 
+ # Optional features
+-config_h.set('USE_OPENSSL', libssl_dep.found())
++config_h.set('USE_OPENSSL', libssl_dep_found)
+ config_h.set('USE_LIBCANBERRA', libcanberra_dep.found())
+ config_h.set('USE_DBUS', dbus_glib_dep.found())
+ config_h.set('USE_PLUGIN', get_option('plugin'))
+@@ -57,7 +66,7 @@
+   join_paths(get_option('prefix'), get_option('libdir'), 'hexchat/plugins')
+ )
  
 -if libssl_dep.found()
 +if libssl_dep_found
    config_h.set('HAVE_X509_GET_SIGNATURE_NID',
      cc.has_function('X509_get_signature_nid', dependencies: libssl_dep)
    )
-@@ -129,9 +139,6 @@ global_ldflags = []
- test_ldflags = [
-   '-Wl,-z,relro',
-   '-Wl,-z,now',
--  # mingw
--  '-Wl,--dynamicbase',
--  '-Wl,--nxcompat',
- ]
- foreach ldflag : test_ldflags
-   if meson.version().version_compare('>= 0.46.0')
+@@ -178,7 +187,7 @@
+   }, section: 'Directories')
+ 
+   summary({
+-    'TLS (openssl)': libssl_dep.found(),
++    'TLS (openssl)': libssl_dep_found,
+     'Plugin Support': get_option('plugin'),
+     'DBus Support': dbus_glib_dep.found(),
+     'libcanberra': libcanberra_dep.found(),
diff --git a/irc/hexchat/files/patch-plugins_sysinfo_meson.build b/irc/hexchat/files/patch-plugins_sysinfo_meson.build
deleted file mode 100644
index b925d3296d7c..000000000000
--- a/irc/hexchat/files/patch-plugins_sysinfo_meson.build
+++ /dev/null
@@ -1,18 +0,0 @@
---- plugins/sysinfo/meson.build.orig	2019-12-22 13:48:33 UTC
-+++ plugins/sysinfo/meson.build
-@@ -13,13 +13,13 @@ sysinfo_includes = []
- sysinfo_cargs = []
- 
- system = host_machine.system()
--if system == 'linux' or system == 'gnu' or system.startswith('gnu/') or system == 'darwin'
-+if system == 'linux' or system == 'gnu' or system.startswith('gnu/') or system == 'darwin' or system == 'freebsd'
-   sysinfo_includes += 'shared'
-   sysinfo_sources += [
-     'shared/df.c'
-   ]
- 
--  if system == 'linux' or system == 'gnu' or system.startswith('gnu/')
-+  if system == 'linux' or system == 'gnu' or system.startswith('gnu/') or system == 'freebsd'
-     libpci = dependency('libpci', required: false, method: 'pkg-config')
-     if libpci.found()
-       sysinfo_deps += libpci
diff --git a/irc/hexchat/files/patch-src__common__server.c b/irc/hexchat/files/patch-src__common__server.c
deleted file mode 100644
index fd3fd906f47e..000000000000
--- a/irc/hexchat/files/patch-src__common__server.c
+++ /dev/null
@@ -1,11 +0,0 @@
---- src/common/server.c.orig	2018-08-29 16:41:08 UTC
-+++ src/common/server.c
-@@ -748,7 +748,7 @@ server_connect_success (server *serv)
- 
- 		/* it'll be a memory leak, if connection isn't terminated by
- 		   server_cleanup() */
--		if ((err = _SSL_set_verify (serv->ctx, ssl_cb_verify, NULL)))
-+		if ((err = _SSL_set_verify (serv->ctx, ssl_cb_verify, "%%CA_BUNDLE%%")))
- 		{
- 			EMIT_SIGNAL (XP_TE_CONNFAIL, serv->server_session, err, NULL,
- 							 NULL, NULL, 0);
diff --git a/irc/hexchat/files/patch-src_common_meson.build b/irc/hexchat/files/patch-src_common_meson.build
new file mode 100644
index 000000000000..159a277f2b28
--- /dev/null
+++ b/irc/hexchat/files/patch-src_common_meson.build
@@ -0,0 +1,11 @@
+--- src/common/meson.build.orig	2021-10-07 15:54:34.995639000 +0200
++++ src/common/meson.build	2021-10-07 15:54:46.304819000 +0200
+@@ -73,7 +73,7 @@
+ #   SIGACTION
+ #   HAVE_GTK_MAC
+ 
+-if libssl_dep.found()
++if libssl_dep_found
+   common_sources += 'ssl.c'
+   common_deps += libssl_dep
+ endif
diff --git a/irc/hexchat/pkg-plist b/irc/hexchat/pkg-plist
index 6a574bdd48ba..d4424ac9952f 100644
--- a/irc/hexchat/pkg-plist
+++ b/irc/hexchat/pkg-plist
@@ -1,70 +1,73 @@
 bin/hexchat
 %%TEXTFE%%bin/hexchat-text
 include/hexchat-plugin.h
 lib/hexchat/plugins/checksum.so
 %%FISHLIM%%lib/hexchat/plugins/fishlim.so
 %%PERL%%lib/hexchat/plugins/perl.so
 lib/hexchat/plugins/python.so
 %%LUA%%lib/hexchat/plugins/lua.so
 %%SYSINFO%%lib/hexchat/plugins/sysinfo.so
+lib/hexchat/python/_hexchat.py
+lib/hexchat/python/hexchat.py
+lib/hexchat/python/xchat.py
 libdata/pkgconfig/hexchat-plugin.pc
 man/man1/hexchat.1.gz
 share/metainfo/io.github.Hexchat.appdata.xml
 share/applications/io.github.Hexchat.desktop
 %%DBUS%%share/dbus-1/services/org.hexchat.service.service
 share/icons/hicolor/48x48/apps/hexchat.png
 share/icons/hicolor/scalable/apps/hexchat.svg
 share/locale/af/LC_MESSAGES/hexchat.mo
 share/locale/am/LC_MESSAGES/hexchat.mo
 share/locale/ast/LC_MESSAGES/hexchat.mo
 share/locale/az/LC_MESSAGES/hexchat.mo
 share/locale/be/LC_MESSAGES/hexchat.mo
 share/locale/bg/LC_MESSAGES/hexchat.mo
 share/locale/ca/LC_MESSAGES/hexchat.mo
 share/locale/cs/LC_MESSAGES/hexchat.mo
 share/locale/da/LC_MESSAGES/hexchat.mo
 share/locale/de/LC_MESSAGES/hexchat.mo
 share/locale/el/LC_MESSAGES/hexchat.mo
 share/locale/en_GB/LC_MESSAGES/hexchat.mo
 share/locale/es/LC_MESSAGES/hexchat.mo
 share/locale/et/LC_MESSAGES/hexchat.mo
 share/locale/eu/LC_MESSAGES/hexchat.mo
 share/locale/fi/LC_MESSAGES/hexchat.mo
 share/locale/fr/LC_MESSAGES/hexchat.mo
 share/locale/gl/LC_MESSAGES/hexchat.mo
 share/locale/gu/LC_MESSAGES/hexchat.mo
 share/locale/hi/LC_MESSAGES/hexchat.mo
 share/locale/hu/LC_MESSAGES/hexchat.mo
 share/locale/id/LC_MESSAGES/hexchat.mo
 share/locale/it/LC_MESSAGES/hexchat.mo
 share/locale/ja_JP/LC_MESSAGES/hexchat.mo
 share/locale/kn/LC_MESSAGES/hexchat.mo
 share/locale/ko/LC_MESSAGES/hexchat.mo
 share/locale/lt/LC_MESSAGES/hexchat.mo
 share/locale/lv/LC_MESSAGES/hexchat.mo
 share/locale/mk/LC_MESSAGES/hexchat.mo
 share/locale/ml/LC_MESSAGES/hexchat.mo
 share/locale/ms/LC_MESSAGES/hexchat.mo
 share/locale/nb/LC_MESSAGES/hexchat.mo
 share/locale/nl/LC_MESSAGES/hexchat.mo
 share/locale/no/LC_MESSAGES/hexchat.mo
 share/locale/pa/LC_MESSAGES/hexchat.mo
 share/locale/pl/LC_MESSAGES/hexchat.mo
 share/locale/pt/LC_MESSAGES/hexchat.mo
 share/locale/pt_BR/LC_MESSAGES/hexchat.mo
 share/locale/ru/LC_MESSAGES/hexchat.mo
 share/locale/rw/LC_MESSAGES/hexchat.mo
 share/locale/sk/LC_MESSAGES/hexchat.mo
 share/locale/sl/LC_MESSAGES/hexchat.mo
 share/locale/sq/LC_MESSAGES/hexchat.mo
 share/locale/sr/LC_MESSAGES/hexchat.mo
 share/locale/sr@latin/LC_MESSAGES/hexchat.mo
 share/locale/sv/LC_MESSAGES/hexchat.mo
 share/locale/th/LC_MESSAGES/hexchat.mo
 share/locale/tr/LC_MESSAGES/hexchat.mo
 share/locale/uk/LC_MESSAGES/hexchat.mo
 share/locale/vi/LC_MESSAGES/hexchat.mo
 share/locale/wa/LC_MESSAGES/hexchat.mo
 share/locale/zh_CN/LC_MESSAGES/hexchat.mo
 share/locale/zh_TW/LC_MESSAGES/hexchat.mo
 share/pixmaps/hexchat.png