diff --git a/net-im/py-matrix-synapse/Makefile b/net-im/py-matrix-synapse/Makefile
index 47fbe7aba7a2..86daae0ccc9a 100644
--- a/net-im/py-matrix-synapse/Makefile
+++ b/net-im/py-matrix-synapse/Makefile
@@ -1,110 +1,118 @@
 # Created by: Brendan Molloy <brendan+freebsd@bbqsrc.net>
 
 PORTNAME=	matrix-synapse
 DISTVERSIONPREFIX=	v
-DISTVERSION=	1.57.1
+DISTVERSION=	1.58.1
 CATEGORIES=	net-im python
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	ports@skyforge.at
 COMMENT=	Matrix protocol reference homeserver
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
+BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}poetry-core>=1.0.0:devel/py-poetry-core@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}poetry2setup>=1.0.0:devel/py-poetry2setup@${PY_FLAVOR}
+
 # Keep the RUN_DEPENDS layout similar to the master/synapse/python_dependencies.py file
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}jsonschema>=3.0.0:devel/py-jsonschema@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}frozendict>=1:devel/py-frozendict@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}unpaddedbase64>=1.1.0:devel/py-unpaddedbase64@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}unpaddedbase64>=2.1.0:devel/py-unpaddedbase64@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}canonicaljson>=1.4.0:devel/py-canonicaljson@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}signedjson>=1.1.0:security/py-signedjson@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pynacl>=1.2.1:security/py-pynacl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}service_identity>=18.1.0:security/py-service_identity@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}twisted>=18.9.0:devel/py-twisted@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}treq>=15.1:www/py-treq@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}openssl>=16.0.0:security/py-openssl@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}yaml>=3.11:devel/py-yaml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyasn1>=0.1.9:devel/py-pyasn1@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pyasn1-modules>=0.0.7:devel/py-pyasn1-modules@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}bcrypt>=3.1.0:security/py-bcrypt@${PY_FLAVOR} \
 		${PY_PILLOW} \
 		${PYTHON_PKGNAMEPREFIX}sortedcontainers>=1.4.4:devel/py-sortedcontainers@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pysaml2>=4.5.0:security/py-pysaml2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pymacaroons>=0.13.0:security/py-pymacaroons@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}msgpack>=0.5.2:devel/py-msgpack@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}phonenumbers>=8.2.0:devel/py-phonenumbers@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}prometheus-client>=0.4.0:net-mgmt/py-prometheus-client@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}attrs>19.2.0:devel/py-attrs@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}attrs>=19.2.0:devel/py-attrs@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}netaddr>=0.7.18:net/py-netaddr@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}Jinja2>=3.0.0:devel/py-Jinja2@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}bleach>=1.4.3:www/py-bleach@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}typing-extensions>=3.10.0:devel/py-typing-extensions@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}cryptography>=0:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}ijson>=3.1.4:devel/py-ijson@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pyjwt>=1.7.0:www/py-pyjwt@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}packaging>=16.1:devel/py-packaging@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}matrix-common>=1.1.0:devel/py-matrix-common@${PY_FLAVOR} \
 		${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}virtualenv>=15.0:devel/py-virtualenv@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}tox>=2.3.1:devel/py-tox@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}lxml>0:devel/py-lxml@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}parameterized>=0.7.0:devel/py-parameterized@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}authlib>=0.14.0:security/py-authlib@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}idna>=2.5:dns/py-idna@${PY_FLAVOR}
 
 USES=		python:3.7+
 USE_GITHUB=	yes
 GH_ACCOUNT=	matrix-org
 GH_PROJECT=	synapse
 USE_PYTHON=	autoplist distutils
 USE_RC_SUBR=	synapse
 
 NO_ARCH=	yes
 SUB_FILES=	pkg-message log.config
 SUB_LIST=	PYTHON_CMD=${PYTHON_CMD} DBDIR=${DBDIR} LOGDIR=${LOGDIR} PIDDIR=${PIDDIR} USERS=${USERS}
 
 USERS=		synapse
 GROUPS=		synapse
 
 DBDIR?=		/var/db/${PORTNAME}
 LOGDIR?=	/var/log/${PORTNAME}
 PIDDIR?=	/var/run/${PORTNAME}
 
 PLIST_FILES=	"@sample ${ETCDIR}/log.config.sample"
 DOCS=		README.rst UPGRADE.rst CHANGES.md docs/postgres.md
 PORTDOCS=	${DOCS:T}
 
-OPTIONS_DEFINE=		DOCS LDAP OIDC  PGSQL REDIS SQLITE URLPREVIEW
+OPTIONS_DEFINE=		DOCS JWT LDAP OIDC PGSQL REDIS SQLITE URLPREVIEW
 OPTIONS_DEFAULT=	PGSQL SQLITE
 
+JWT_DESC=		Add dependencies for JSON web tokens
 OIDC_DESC=		Add dependencies for OpenID Connect based logins
 REDIS_DESC=		Add support replication over Redis for synapse workers
 URLPREVIEW_DESC=	Add dependencies necessary for URL previews
 
+JWT_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pyjwt>=1.6.4:www/py-pyjwt@${PY_FLAVOR}
 LDAP_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}matrix-synapse-ldap3>=0.1:net/py-matrix-synapse-ldap3@${PY_FLAVOR}
 OIDC_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}authlib>=0.14.0:security/py-authlib@${PY_FLAVOR}
 PGSQL_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}psycopg2>2.8:databases/py-psycopg2@${PY_FLAVOR}
 REDIS_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}hiredis>=0:databases/py-hiredis@${PY_FLAVOR} \
 			${PYTHON_PKGNAMEPREFIX}txredisapi>=1.4.7:databases/py-txredisapi@${PY_FLAVOR}
 SQLITE_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sqlite3>0:databases/py-sqlite3@${PY_FLAVOR}
 URLPREVIEW_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}lxml>=4.2.0:devel/py-lxml@${PY_FLAVOR}
 
 .include <bsd.port.pre.mk>
 
 # Dependency required by Python < 3.8
 .if (${PYTHON_REL} < 30800)
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}importlib-metadata>=1.4:devel/py-importlib-metadata@${PY_FLAVOR}
 .endif
 
+pre-configure:
+	cd ${WRKSRC} && poetry2setup > setup.py
+
 post-install:
 	${MKDIR} ${STAGEDIR}${ETCDIR}
 	${INSTALL_DATA} ${WRKDIR}/log.config ${STAGEDIR}${ETCDIR}/log.config.sample
 
 post-install-DOCS-on:
 	${MKDIR} ${STAGEDIR}${DOCSDIR}
 	${INSTALL_DATA} ${DOCS:S|^|${WRKSRC}/|} ${STAGEDIR}${DOCSDIR}
 
 do-test:
 	cd ${WRKSRC} && PYTHONPATH="." trial-${PYTHON_VER} tests
 
 .include <bsd.port.post.mk>
diff --git a/net-im/py-matrix-synapse/distinfo b/net-im/py-matrix-synapse/distinfo
index d0ba9224cbf1..363ca167e23f 100644
--- a/net-im/py-matrix-synapse/distinfo
+++ b/net-im/py-matrix-synapse/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1650652816
-SHA256 (matrix-org-synapse-v1.57.1_GH0.tar.gz) = 07926e1601bd2973ea16baabd41268939ceeb90f6a8c98b31a3610de61dc5ad1
-SIZE (matrix-org-synapse-v1.57.1_GH0.tar.gz) = 7834623
+TIMESTAMP = 1651864723
+SHA256 (matrix-org-synapse-v1.58.1_GH0.tar.gz) = 3e64e102ee9e848c70b923a68001990541bb749e9fb3fe2cf4f643ad40955add
+SIZE (matrix-org-synapse-v1.58.1_GH0.tar.gz) = 7881275
diff --git a/net-im/py-matrix-synapse/files/patch-pyproject.toml b/net-im/py-matrix-synapse/files/patch-pyproject.toml
new file mode 100644
index 000000000000..903aba718c30
--- /dev/null
+++ b/net-im/py-matrix-synapse/files/patch-pyproject.toml
@@ -0,0 +1,11 @@
+--- pyproject.toml.orig	2022-05-07 18:29:37 UTC
++++ pyproject.toml
+@@ -146,7 +146,7 @@ bleach = ">=1.4.3"
+ typing-extensions = ">=3.10.0"
+ # We enforce that we have a `cryptography` version that bundles an `openssl`
+ # with the latest security patches.
+-cryptography = ">=3.4.7"
++cryptography = "*"
+ # ijson 3.1.4 fixes a bug with "." in property names
+ ijson = ">=3.1.4"
+ matrix-common = "~=1.1.0"
diff --git a/net-im/py-matrix-synapse/files/patch-synapse_python__dependencies.py b/net-im/py-matrix-synapse/files/patch-synapse_python__dependencies.py
deleted file mode 100644
index 2cace56065f0..000000000000
--- a/net-im/py-matrix-synapse/files/patch-synapse_python__dependencies.py
+++ /dev/null
@@ -1,11 +0,0 @@
---- synapse/python_dependencies.py.orig	2022-04-20 00:17:17 UTC
-+++ synapse/python_dependencies.py
-@@ -82,7 +82,7 @@ REQUIREMENTS = [
-     "typing-extensions>=3.10.0",
-     # We enforce that we have a `cryptography` version that bundles an `openssl`
-     # with the latest security patches.
--    "cryptography>=3.4.7",
-+    "cryptography",
-     # ijson 3.1.4 fixes a bug with "." in property names
-     "ijson>=3.1.4",
-     "matrix-common~=1.1.0",
diff --git a/net-im/py-matrix-synapse/files/pkg-message.in b/net-im/py-matrix-synapse/files/pkg-message.in
index 5041454e8d04..7121cf97a00f 100644
--- a/net-im/py-matrix-synapse/files/pkg-message.in
+++ b/net-im/py-matrix-synapse/files/pkg-message.in
@@ -1,77 +1,86 @@
 [
 { type: install
   message: <<EOM
 Configuring Synapse:
 
 The following command can be used to generate a sample configuration of synapse:
 
 %%PYTHON_CMD%% -B -m synapse.app.homeserver -c %%ETCDIR%%/homeserver.yaml --generate-config -H <SERVER_NAME> --report-stats no
 
 Please note that you will still need to manually configure paths to log
 directory, database, and media storage with this method.
 EOM
 }
 { type: upgrade
   message: <<EOM
 If you're upgrading from a previous release of synapse, please read the upgrade
 instructions at %%DOCSDIR%%/UPGRADE.rst
 EOM
 }
 { type: upgrade
   maximum_version: 1.51.0
   message: <<EOM
 Synapse 1.51.0 deprecates webclient listeners and non-HTTP(S)
 web_client_location settings. Please update your homeserver configurations
 accordingly.
 
 Additionally, if you run your own turn server for WebRTC and
 use Let's Encrypt certificates, be advised that some Android and iOS clients
 may be unable to connect. Please see upstream's turn-howto[0] for additional
 details on this issue.
 
 [0] https://matrix-org.github.io/synapse/latest/turn-howto.html
 
 EOM
 }
 { type: upgrade
   maximum_version: 1.55.0
   message: <<EOM
 The default room version of synapse has been increased to version 9. Consider
 changing this if interoperability with other matrix servers is an issue.
 
 If you're using Mjolnir, be advised that this version of synapse is
 incompatible with Mjolnir 1.3.1 and earlier.
 
 EOM
 }
 {
   message: <<EOM
 Running synapse with the sqlite backend is only recommended for testing purposes.
 Future versions of synapse will disable federation by default if sqlite is used.
 EOM
 }
 { type: upgrade
   message: <<EOM
 If you're currently using synapse with sqlite and would like to switch to postgres,
 please read the instructions at %%DOCSDIR%%/postgres.md
 EOM
 }
 { type: upgrade
   maximum_version: 1.55.2
   message: <<EOM
 Synapse will now refuse to start up if open registration is enabled, in order to help
 mitigate abuse across the federation. If you would like to provide registration to
 anyone, consider adding email, recaptcha or token-based verification in order to
 prevent automated registration from bad actors. This check can be disabled by setting
 the enable_registration_without_verification option in your homeserver configuration
 file to true. More details are available in the upgrade notes[0].
 
 Synapse will additionally now refuse to start when using PostgreSQL with a non-C values
 for COLLATE and CTYPE, unless the config flag allow_unsafe_locale, found in the database
 section of the configuration file, is set to true. See the upgrade notes[1] for details.
 
 [0] https://matrix-org.github.io/synapse/v1.56/upgrade.html#open-registration-without-verification-is-now-disabled-by-default
 [1] https://matrix-org.github.io/synapse/v1.56/upgrade#change-in-behaviour-for-postgresql-databases-with-unsafe-locale
 EOM
 }
+{ type: upgrade
+  maximum_version: 1.62.0
+  message: <<EOM
+Starting with synapse 1.62.0, this port will no longer ship with sqlite support
+by default. If you rely on sqlite for your setup, please either migrate to
+postfix, install the sqlite dependency manually or build a custom flavor of the
+port.
+EOM
+}
 ]