diff -Naur py-matrix-synapse.orig/Makefile py-matrix-synapse/Makefile
--- py-matrix-synapse.orig/Makefile	2019-04-18 20:33:46.000000000 +0000
+++ py-matrix-synapse/Makefile	2019-06-07 19:01:45.468303000 +0000
@@ -3,7 +3,7 @@
 
 PORTNAME=	matrix-synapse
 DISTVERSIONPREFIX=	v
-DISTVERSION=	0.99.3
+DISTVERSION=	0.99.5.2
 CATEGORIES=	net-im python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
@@ -29,7 +29,7 @@
 		${PYTHON_PKGNAMEPREFIX}pyasn1-modules>=0.0.7:devel/py-pyasn1-modules@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}daemonize>=2.4.2:devel/py-daemonize@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}bcrypt>=3.1.0:security/py-bcrypt@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pillow>=3.1.2:graphics/py-pillow@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pillow>=4.3.0:graphics/py-pillow@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}sortedcontainers>=1.4.4:devel/py-sortedcontainers@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}psutil>=2.0.0:sysutils/py-psutil@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pysaml2>=4.0.2:security/py-pysaml2@${PY_FLAVOR} \
@@ -71,17 +71,19 @@
 
 NO_ARCH=	yes
 
-OPTIONS_DEFINE=		EMAIL LDAP PGSQL SQLITE URLPREVIEW
-OPTIONS_DEFAULT=	SQLITE
+OPTIONS_DEFINE=		EMAIL LDAP PGSQL SQLITE URLPREVIEW DOCS
+OPTIONS_DEFAULT=	SQLITE DOCS
 EMAIL_DESC=		Email notifications for missed messages
 URLPREVIEW_DESC=	Add dependencies necessary for URL previews
 URLPREVIEW_RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}lxml>=3.5.0:devel/py-lxml@${PY_FLAVOR}
 EMAIL_RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}Jinja2>=2.9:devel/py-Jinja2@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}bleach>=1.4.2:www/py-bleach@${PY_FLAVOR}
 LDAP_RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}matrix-synapse-ldap3>=0.1:net/py-matrix-synapse-ldap3@${PY_FLAVOR}
-PGSQL_RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}psycopg2>2.6:databases/py-psycopg2@${PY_FLAVOR}
+PGSQL_RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}psycopg2>2.7:databases/py-psycopg2@${PY_FLAVOR}
 SQLITE_RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}sqlite3>0:databases/py-sqlite3@${PY_FLAVOR}
 
+
+PORTDOCS=README.rst UPGRADE.rst CHANGES.md
 post-patch:
 	@${REINPLACE_CMD} -e 's|msgpack-python|msgpack|' ${WRKSRC}/synapse/python_dependencies.py
 
@@ -91,5 +93,9 @@
 post-install:
 	${MKDIR} ${STAGEDIR}${ETCDIR}
 	${INSTALL_DATA} ${WRKDIR}/log.config ${STAGEDIR}${ETCDIR}/log.config.sample
+
+post-install-DOCS-on:
+	${MKDIR} ${STAGEDIR}${DOCSDIR}
+	${INSTALL_DATA} ${PORTDOCS:S|^|${WRKSRC}/|} ${STAGEDIR}${DOCSDIR}
 
 .include <bsd.port.mk>
diff -Naur py-matrix-synapse.orig/distinfo py-matrix-synapse/distinfo
--- py-matrix-synapse.orig/distinfo	2019-04-18 20:33:46.000000000 +0000
+++ py-matrix-synapse/distinfo	2019-06-07 12:55:39.871605000 +0000
@@ -1,3 +1,3 @@
-TIMESTAMP = 1555070432
-SHA256 (matrix-org-synapse-v0.99.3_GH0.tar.gz) = 60a2b4caaed3e23a8fe9b43406dbee695d60271650f332cf3df3fce675a68274
-SIZE (matrix-org-synapse-v0.99.3_GH0.tar.gz) = 1227964
+TIMESTAMP = 1559912139
+SHA256 (matrix-org-synapse-v0.99.5.2_GH0.tar.gz) = 0b820a1fbf81a4db2cd04f806f9a463dfcd8c0cd799701a4104e652431a6920b
+SIZE (matrix-org-synapse-v0.99.5.2_GH0.tar.gz) = 1277988
diff -Naur py-matrix-synapse.orig/files/pkg-message.in py-matrix-synapse/files/pkg-message.in
--- py-matrix-synapse.orig/files/pkg-message.in	2019-04-18 20:33:46.000000000 +0000
+++ py-matrix-synapse/files/pkg-message.in	2019-06-07 19:05:38.753101000 +0000
@@ -12,3 +12,6 @@
 with previous versions will no longer suffice. Please ensure that the
 certificate specified by the "tls_certificate_path" option in your
 homeserver.yaml points to a valid certificate.
+
+If you're upgrading from a previous release of synapse, please read the upgrade
+instructions at %%DOCSDIR%%/UPGRADE.rst