diff --git a/pkgs/development/python-modules/signedjson/default.nix b/pkgs/development/python-modules/signedjson/default.nix
index 33a615fefd46..1214730dad87 100644
--- a/pkgs/development/python-modules/signedjson/default.nix
+++ b/pkgs/development/python-modules/signedjson/default.nix
@@ -4,19 +4,20 @@
 , canonicaljson
 , unpaddedbase64
 , pynacl
+, typing-extensions
 }:
 
 buildPythonPackage rec {
   pname = "signedjson";
-  version = "1.0.0";
+  version = "1.1.0";
 
   src = fetchgit {
     url = "https://github.com/matrix-org/python-signedjson.git";
     rev = "refs/tags/v${version}";
-    sha256 = "0b8xxhc3npd4567kqapfp4gs7m0h057xam3an7424az262ind82n";
+    sha256 = "18s388hm3babnvakbbgfqk0jzq25nnznvhygywd3azp9b4yzmd5c";
   };
 
-  propagatedBuildInputs = [ canonicaljson unpaddedbase64 pynacl ];
+  propagatedBuildInputs = [ canonicaljson unpaddedbase64 pynacl typing-extensions ];
 
   meta = with stdenv.lib; {
     homepage = https://pypi.org/project/signedjson/;
diff --git a/pkgs/servers/mail/opensmtpd/default.nix b/pkgs/servers/mail/opensmtpd/default.nix
index 22744b36d432..83365dc099c5 100644
--- a/pkgs/servers/mail/opensmtpd/default.nix
+++ b/pkgs/servers/mail/opensmtpd/default.nix
@@ -1,33 +1,26 @@
 { stdenv, fetchurl, autoconf, automake, libtool, bison
-, libasr, libevent, zlib, libressl, db, pam, nixosTests
+, libasr, libevent, zlib, openssl, db, pam, nixosTests
 }:
 
 stdenv.mkDerivation rec {
   pname = "opensmtpd";
-  version = "6.4.2p1";
+  version = "6.6.4p1";
 
   nativeBuildInputs = [ autoconf automake libtool bison ];
-  buildInputs = [ libasr libevent zlib libressl db pam ];
+  buildInputs = [ libasr libevent zlib openssl db pam ];
 
   src = fetchurl {
     url = "https://www.opensmtpd.org/archives/${pname}-${version}.tar.gz";
-    sha256 = "0pgv080ai7d98l9340jadp9wjiaqj2qvgpqhilcz0kps2mdiawbd";
+    sha256 = "1kyph9ycq0j21dl9n1sq5fns9p4gckdi0fmnf8awrcwrdcm9dyg2";
   };
 
   patches = [
     ./proc_path.diff # TODO: upstream to OpenSMTPD, see https://github.com/NixOS/nixpkgs/issues/54045
-    (fetchurl {
-      name = "CVE-2020-7247.patch";
-      url = "https://github.com/OpenSMTPD/OpenSMTPD/commit/d2688c097e0ff53037c7403e09426771876a3907.patch";
-      sha256 = "1mr5zb7mgpapf80xrcjvvzinzyiqcd3i0z4jwj11wl3zrfq5kwwn";
-    })
   ];
 
   # See https://github.com/OpenSMTPD/OpenSMTPD/issues/885 for the `sh bootstrap`
   # requirement
   postPatch = ''
-    substituteInPlace smtpd/parse.y \
-      --replace "/usr/libexec/" "$out/libexec/opensmtpd/"
     substituteInPlace mk/smtpctl/Makefile.am --replace "chgrp" "true"
     substituteInPlace mk/smtpctl/Makefile.am --replace "chmod 2555" "chmod 0555"
     sh bootstrap
diff --git a/pkgs/servers/matrix-synapse/default.nix b/pkgs/servers/matrix-synapse/default.nix
index 926999ce7f1b..20081e25d431 100644
--- a/pkgs/servers/matrix-synapse/default.nix
+++ b/pkgs/servers/matrix-synapse/default.nix
@@ -23,11 +23,11 @@ let
 
 in buildPythonApplication rec {
   pname = "matrix-synapse";
-  version = "1.9.1";
+  version = "1.11.1";
 
   src = fetchPypi {
     inherit pname version;
-    sha256 = "13csf18dchm75vw251a7h57diag94vw6rhg8kkkbpi35cibn0cz2";
+    sha256 = "0xd4bxsmk67r6pfj5lh0hn36r8z51mxsl39fjfrfdidvl1qqbxnk";
   };
 
   patches = [
diff --git a/pkgs/servers/nextcloud/default.nix b/pkgs/servers/nextcloud/default.nix
index 1e7bfc7835db..9472bd3475ed 100644
--- a/pkgs/servers/nextcloud/default.nix
+++ b/pkgs/servers/nextcloud/default.nix
@@ -2,11 +2,11 @@
 
 stdenv.mkDerivation rec {
   pname = "nextcloud";
-  version = "16.0.8";
+  version = "16.0.9";
 
   src = fetchurl {
     url = "https://download.nextcloud.com/server/releases/${pname}-${version}.tar.bz2";
-    sha256 = "0c5z46936pxsmh5isgj5d8pcj1sy9hcqdi55awz5axs7h5cvabr5";
+    sha256 = "0ds9awn4fqjizf4pz35aa9rg1pf3mrghbbp2wyyzb73zk0n10dg1";
   };
 
   installPhase = ''