diff --git a/nixos/modules/services/web-apps/discourse.nix b/nixos/modules/services/web-apps/discourse.nix
index 8d5302ba267..050e4ee3d32 100644
--- a/nixos/modules/services/web-apps/discourse.nix
+++ b/nixos/modules/services/web-apps/discourse.nix
@@ -771,7 +771,6 @@ in
           "tmp"
           "assets/javascripts/plugins"
           "public"
-          "plugins"
           "sockets"
         ];
         RuntimeDirectoryMode = 0750;
diff --git a/nixos/modules/services/web-apps/discourse.xml b/nixos/modules/services/web-apps/discourse.xml
index 1d6866e7b35..184c9c6363e 100644
--- a/nixos/modules/services/web-apps/discourse.xml
+++ b/nixos/modules/services/web-apps/discourse.xml
@@ -284,11 +284,22 @@ services.discourse = {
       Ruby dependencies are listed in its
       <filename>plugin.rb</filename> file as function calls to
       <literal>gem</literal>. To construct the corresponding
-      <filename>Gemfile</filename>, run <command>bundle
+      <filename>Gemfile</filename> manually, run <command>bundle
       init</command>, then add the <literal>gem</literal> lines to it
       verbatim.
     </para>
 
+    <para>
+      Much of the packaging can be done automatically by the
+      <filename>nixpkgs/pkgs/servers/web-apps/discourse/update.py</filename>
+      script - just add the plugin to the <literal>plugins</literal>
+      list in the <function>update_plugins</function> function and run
+      the script:
+      <programlisting language="bash">
+./update.py update-plugins
+</programlisting>.
+    </para>
+
     <para>
       Some plugins provide <link
       linkend="module-services-discourse-site-settings">site
diff --git a/nixos/tests/discourse.nix b/nixos/tests/discourse.nix
index 2ed6fb957c2..7dd39085a00 100644
--- a/nixos/tests/discourse.nix
+++ b/nixos/tests/discourse.nix
@@ -4,7 +4,7 @@
 #  3. replying to that message via email.
 
 import ./make-test-python.nix (
-  { pkgs, lib, ... }:
+  { pkgs, lib, package ? pkgs.discourse, ... }:
   let
     certs = import ./common/acme/server/snakeoil-certs.nix;
     clientDomain = "client.fake.domain";
@@ -55,7 +55,7 @@ import ./make-test-python.nix (
 
         services.discourse = {
           enable = true;
-          inherit admin;
+          inherit admin package;
           hostname = discourseDomain;
           sslCertificate = "${certs.${discourseDomain}.cert}";
           sslCertificateKey = "${certs.${discourseDomain}.key}";
diff --git a/pkgs/servers/web-apps/discourse/auto_generated_path.patch b/pkgs/servers/web-apps/discourse/auto_generated_path.patch
new file mode 100644
index 00000000000..9dcb1cb5595
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/auto_generated_path.patch
@@ -0,0 +1,13 @@
+diff --git a/lib/plugin/instance.rb b/lib/plugin/instance.rb
+index 380a63e987..b2ce7fa982 100644
+--- a/lib/plugin/instance.rb
++++ b/lib/plugin/instance.rb
+@@ -403,7 +403,7 @@ class Plugin::Instance
+   end
+ 
+   def auto_generated_path
+-    File.dirname(path) << "/auto_generated"
++    "#{Rails.root}/public/assets/auto_generated_plugin_assets/#{name}"
+   end
+ 
+   def after_initialize(&block)
diff --git a/pkgs/servers/web-apps/discourse/default.nix b/pkgs/servers/web-apps/discourse/default.nix
index de171cebd41..59e3d4b18e9 100644
--- a/pkgs/servers/web-apps/discourse/default.nix
+++ b/pkgs/servers/web-apps/discourse/default.nix
@@ -1,4 +1,4 @@
-{ stdenv, makeWrapper, runCommandNoCC, lib, nixosTests, writeShellScript
+{ stdenv, pkgs, makeWrapper, runCommandNoCC, lib, writeShellScript
 , fetchFromGitHub, bundlerEnv, callPackage
 
 , ruby, replace, gzip, gnutar, git, cacert, util-linux, gawk
@@ -6,16 +6,16 @@
 , redis, postgresql, which, brotli, procps, rsync, nodePackages, v8
 
 , plugins ? []
-}:
+}@args:
 
 let
-  version = "2.7.5";
+  version = "2.7.7";
 
   src = fetchFromGitHub {
     owner = "discourse";
     repo = "discourse";
     rev = "v${version}";
-    sha256 = "sha256-OykWaiBAHcZy41i+aRzBHCRgwnfQUBijHjb+ofIk25M=";
+    sha256 = "sha256-rhcTQyirgPX0ITjgotJAYLLSU957GanxAYYhy9j123U=";
   };
 
   runtimeDeps = [
@@ -55,6 +55,7 @@ let
     , version ? null
     , meta ? null
     , bundlerEnvArgs ? {}
+    , preserveGemsDir ? false
     , src
     , ...
     }@args:
@@ -65,16 +66,26 @@ let
     in
       stdenv.mkDerivation (builtins.removeAttrs args [ "bundlerEnvArgs" ] // {
         pluginName = if name != null then name else "${pname}-${version}";
-        phases = [ "unpackPhase" "installPhase" ];
+        dontConfigure = true;
+        dontBuild = true;
         installPhase = ''
           runHook preInstall
           mkdir -p $out
           cp -r * $out/
-        '' + lib.optionalString (bundlerEnvArgs != {}) ''
-          ln -sf ${rubyEnv}/lib/ruby/gems $out/gems
-        '' + ''
+        '' + lib.optionalString (bundlerEnvArgs != {}) (
+          if preserveGemsDir then ''
+            cp -r ${rubyEnv}/lib/ruby/gems/* $out/gems/
+          ''
+          else ''
+            if [[ -e $out/gems ]]; then
+              echo "Warning: The repo contains a 'gems' directory which will be removed!"
+              echo "         If you need to preserve it, set 'preserveGemsDir = true'."
+              rm -r $out/gems
+            fi
+            ln -sf ${rubyEnv}/lib/ruby/gems $out/gems
+          '' + ''
           runHook postInstall
-        '';
+        '');
       });
 
   rake = runCommandNoCC "discourse-rake" {
@@ -156,6 +167,11 @@ let
       # Use the Ruby API version in the plugin gem path, to match the
       # one constructed by bundlerEnv
       ./plugin_gem_api_version.patch
+
+      # Change the path to the auto generated plugin assets, which
+      # defaults to the plugin's directory and isn't writable at the
+      # time of asset generation
+      ./auto_generated_path.patch
     ];
 
     # We have to set up an environment that is close enough to
@@ -242,6 +258,11 @@ let
       # Use mv instead of rename, since rename doesn't work across
       # device boundaries
       ./use_mv_instead_of_rename.patch
+
+      # Change the path to the auto generated plugin assets, which
+      # defaults to the plugin's directory and isn't writable at the
+      # time of asset generation
+      ./auto_generated_path.patch
     ];
 
     postPatch = ''
@@ -272,7 +293,6 @@ let
       ln -sf /run/discourse/config $out/share/discourse/config
       ln -sf /run/discourse/assets/javascripts/plugins $out/share/discourse/app/assets/javascripts/plugins
       ln -sf /run/discourse/public $out/share/discourse/public
-      ln -sf /run/discourse/plugins $out/share/discourse/plugins
       ln -sf ${assets} $out/share/discourse/public.dist/assets
       ${lib.concatMapStringsSep "\n" (p: "ln -sf ${p} $out/share/discourse/plugins/${p.pluginName or ""}") plugins}
 
@@ -292,7 +312,7 @@ let
       enabledPlugins = plugins;
       plugins = callPackage ./plugins/all-plugins.nix { inherit mkDiscoursePlugin; };
       ruby = rubyEnv.wrappedRuby;
-      tests = nixosTests.discourse;
+      tests = import ../../../../nixos/tests/discourse.nix { package = pkgs.discourse.override args; };
     };
   };
 in discourse
diff --git a/pkgs/servers/web-apps/discourse/plugins/all-plugins.nix b/pkgs/servers/web-apps/discourse/plugins/all-plugins.nix
index f64fbb137df..27c749dea2e 100644
--- a/pkgs/servers/web-apps/discourse/plugins/all-plugins.nix
+++ b/pkgs/servers/web-apps/discourse/plugins/all-plugins.nix
@@ -3,9 +3,13 @@ let
   callPackage = newScope args;
 in
 {
+  discourse-calendar = callPackage ./discourse-calendar {};
   discourse-canned-replies = callPackage ./discourse-canned-replies {};
+  discourse-checklist = callPackage ./discourse-checklist {};
+  discourse-data-explorer = callPackage ./discourse-data-explorer {};
   discourse-github = callPackage ./discourse-github {};
   discourse-math = callPackage ./discourse-math {};
+  discourse-migratepassword = callPackage ./discourse-migratepassword {};
   discourse-solved = callPackage ./discourse-solved {};
   discourse-spoiler-alert = callPackage ./discourse-spoiler-alert {};
   discourse-yearly-review = callPackage ./discourse-yearly-review {};
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/Gemfile b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/Gemfile
new file mode 100644
index 00000000000..bda8e6ec3cf
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/Gemfile
@@ -0,0 +1,8 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+git_source(:github) { |repo_name| "https://github.com/#{repo_name}" }
+
+# gem "rails"
+gem 'rrule', '0.4.2', require: false
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/Gemfile.lock b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/Gemfile.lock
new file mode 100644
index 00000000000..d5622c0ac37
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/Gemfile.lock
@@ -0,0 +1,27 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    activesupport (6.1.4)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
+    concurrent-ruby (1.1.9)
+    i18n (1.8.10)
+      concurrent-ruby (~> 1.0)
+    minitest (5.14.4)
+    rrule (0.4.2)
+      activesupport (>= 4.1)
+    tzinfo (2.0.4)
+      concurrent-ruby (~> 1.0)
+    zeitwerk (2.4.2)
+
+PLATFORMS
+  ruby
+
+DEPENDENCIES
+  rrule (= 0.4.2)
+
+BUNDLED WITH
+   2.2.20
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/default.nix
new file mode 100644
index 00000000000..b610a5c21a1
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/default.nix
@@ -0,0 +1,18 @@
+{ lib, mkDiscoursePlugin, fetchFromGitHub }:
+
+mkDiscoursePlugin {
+  name = "discourse-calendar";
+  bundlerEnvArgs.gemdir = ./.;
+  src = fetchFromGitHub {
+    owner = "discourse";
+    repo = "discourse-calendar";
+    rev = "519cf403ae3003291de20145aca243e2ffbcb4a2";
+    sha256 = "0398cf7k03i7j7v5w1mysjzk2npbkvr7icj5sjwa8i8xzg34gck4";
+  };
+  meta = with lib; {
+    homepage = "https://github.com/discourse/discourse-calendar";
+    maintainers = with maintainers; [ ryantm ];
+    license = licenses.mit;
+    description = "Adds the ability to create a dynamic calendar in the first post of a topic";
+  };
+}
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/gemset.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/gemset.nix
new file mode 100644
index 00000000000..26db0e6fd10
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-calendar/gemset.nix
@@ -0,0 +1,76 @@
+{
+  activesupport = {
+    dependencies = ["concurrent-ruby" "i18n" "minitest" "tzinfo" "zeitwerk"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0kqgywy4cj3h5142dh7pl0xx5nybp25jn0ykk0znziivzks68xdk";
+      type = "gem";
+    };
+    version = "6.1.4";
+  };
+  concurrent-ruby = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0nwad3211p7yv9sda31jmbyw6sdafzmdi2i2niaz6f0wk5nq9h0f";
+      type = "gem";
+    };
+    version = "1.1.9";
+  };
+  i18n = {
+    dependencies = ["concurrent-ruby"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0g2fnag935zn2ggm5cn6k4s4xvv53v2givj1j90szmvavlpya96a";
+      type = "gem";
+    };
+    version = "1.8.10";
+  };
+  minitest = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "19z7wkhg59y8abginfrm2wzplz7py3va8fyngiigngqvsws6cwgl";
+      type = "gem";
+    };
+    version = "5.14.4";
+  };
+  rrule = {
+    dependencies = ["activesupport"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "0w338b7dgvd144fl5b8xy2lfc6zgbcjac7b4z158jc8h070yzc9v";
+      type = "gem";
+    };
+    version = "0.4.2";
+  };
+  tzinfo = {
+    dependencies = ["concurrent-ruby"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "10qp5x7f9hvlc0psv9gsfbxg4a7s0485wsbq1kljkxq94in91l4z";
+      type = "gem";
+    };
+    version = "2.0.4";
+  };
+  zeitwerk = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1746czsjarixq0x05f7p3hpzi38ldg6wxnxxw74kbjzh1sdjgmpl";
+      type = "gem";
+    };
+    version = "2.4.2";
+  };
+}
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-canned-replies/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-canned-replies/default.nix
index 558abec36f4..f90fabc0574 100644
--- a/pkgs/servers/web-apps/discourse/plugins/discourse-canned-replies/default.nix
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-canned-replies/default.nix
@@ -5,8 +5,8 @@ mkDiscoursePlugin {
   src = fetchFromGitHub {
     owner = "discourse";
     repo = "discourse-canned-replies";
-    rev = "e3f1de8928df5955b64994079b7e2073556e5456";
-    sha256 = "1g4fazm6cn6hbfd08mq2zhc6dgm4qj1r1f1amhbgxhk6qsxf42cd";
+    rev = "672a96a8160d3767cf5fd6647309c7b5dcf8a55d";
+    sha256 = "105zgpc7j3xmlkaz3cgxw1rfgy5d3dzln58ix569jmzifbsijml7";
   };
   meta = with lib; {
     homepage = "https://github.com/discourse/discourse-canned-replies";
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-checklist/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-checklist/default.nix
new file mode 100644
index 00000000000..89edb3f71d7
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-checklist/default.nix
@@ -0,0 +1,17 @@
+{ lib, mkDiscoursePlugin, fetchFromGitHub }:
+
+mkDiscoursePlugin {
+  name = "discourse-checklist";
+  src = fetchFromGitHub {
+    owner = "discourse";
+    repo = "discourse-checklist";
+    rev = "6e7b9c5040c55795c7fd4db9569b3e93dad092c2";
+    sha256 = "sha256-2KAVBrfAvhLZC9idi+ijbVqOCq9rSXbDVEOZS+mWJ10=";
+  };
+  meta = with lib; {
+    homepage = "https://github.com/discourse/discourse-checklist";
+    maintainers = with maintainers; [ ryantm ];
+    license = licenses.gpl2Only;
+    description = "A simple checklist rendering plugin for discourse ";
+  };
+}
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-data-explorer/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-data-explorer/default.nix
new file mode 100644
index 00000000000..90218759cac
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-data-explorer/default.nix
@@ -0,0 +1,17 @@
+{ lib, mkDiscoursePlugin, fetchFromGitHub }:
+
+mkDiscoursePlugin {
+  name = "discourse-data-explorer";
+  src = fetchFromGitHub {
+    owner = "discourse";
+    repo = "discourse-data-explorer";
+    rev = "23287ece952cb45203819e7b470ebc194c58cb13";
+    sha256 = "1vc2072r72fkvcfpy6vpn9x4gl9lpjk29pnj8095xs22im8j5in1";
+  };
+  meta = with lib; {
+    homepage = "https://github.com/discourse/discourse-data-explorer";
+    maintainers = with maintainers; [ ryantm ];
+    license = licenses.mit;
+    description = "SQL Queries for admins in Discourse";
+  };
+}
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-github/Gemfile.lock b/pkgs/servers/web-apps/discourse/plugins/discourse-github/Gemfile.lock
index 0486ea1402b..b6ebd834a53 100644
--- a/pkgs/servers/web-apps/discourse/plugins/discourse-github/Gemfile.lock
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-github/Gemfile.lock
@@ -3,7 +3,7 @@ GEM
   specs:
     addressable (2.8.0)
       public_suffix (>= 2.0.2, < 5.0)
-    faraday (1.5.0)
+    faraday (1.7.0)
       faraday-em_http (~> 1.0)
       faraday-em_synchrony (~> 1.0)
       faraday-excon (~> 1.1)
@@ -11,6 +11,7 @@ GEM
       faraday-net_http (~> 1.0)
       faraday-net_http_persistent (~> 1.1)
       faraday-patron (~> 1.0)
+      faraday-rack (~> 1.0)
       multipart-post (>= 1.2, < 3)
       ruby2_keywords (>= 0.0.4)
     faraday-em_http (1.0.0)
@@ -18,20 +19,21 @@ GEM
     faraday-excon (1.1.0)
     faraday-httpclient (1.0.1)
     faraday-net_http (1.0.1)
-    faraday-net_http_persistent (1.1.0)
+    faraday-net_http_persistent (1.2.0)
     faraday-patron (1.0.0)
+    faraday-rack (1.0.0)
     multipart-post (2.1.1)
     octokit (4.21.0)
       faraday (>= 0.9)
       sawyer (~> 0.8.0, >= 0.5.3)
     public_suffix (4.0.6)
-    ruby2_keywords (0.0.4)
+    ruby2_keywords (0.0.5)
     sawyer (0.8.2)
       addressable (>= 2.3.5)
       faraday (> 0.8, < 2.0)
 
 PLATFORMS
-  x86_64-linux
+  ruby
 
 DEPENDENCIES
   octokit (= 4.21.0)
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-github/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-github/default.nix
index bb6d16bfe46..63488de18ff 100644
--- a/pkgs/servers/web-apps/discourse/plugins/discourse-github/default.nix
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-github/default.nix
@@ -6,8 +6,8 @@ mkDiscoursePlugin {
   src = fetchFromGitHub {
     owner = "discourse";
     repo = "discourse-github";
-    rev = "154fd5ea597640c2259ce489b4ce75b48ac1973c";
-    sha256 = "0wb5p219z42rc035rnh2iwrbsj000nxa9shbmc325rzcg6xlhdhw";
+    rev = "b6ad8e39a13e2ad5c6943ea697ca23f2c5f9fec1";
+    sha256 = "0vxwp4kbf44clcqilb8ni0ykk4jrgiv4rbd05pgfvndcp3izm2i6";
   };
   meta = with lib; {
     homepage = "https://github.com/discourse/discourse-github";
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-github/gemset.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-github/gemset.nix
index ae20ec89521..90009a3beb8 100644
--- a/pkgs/servers/web-apps/discourse/plugins/discourse-github/gemset.nix
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-github/gemset.nix
@@ -11,15 +11,15 @@
     version = "2.8.0";
   };
   faraday = {
-    dependencies = ["faraday-em_http" "faraday-em_synchrony" "faraday-excon" "faraday-httpclient" "faraday-net_http" "faraday-net_http_persistent" "faraday-patron" "multipart-post" "ruby2_keywords"];
+    dependencies = ["faraday-em_http" "faraday-em_synchrony" "faraday-excon" "faraday-httpclient" "faraday-net_http" "faraday-net_http_persistent" "faraday-patron" "faraday-rack" "multipart-post" "ruby2_keywords"];
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0gwbii45plm9bljk22bwzhzxrc5xid8qx24f54vrm74q3zaz00ah";
+      sha256 = "0r6ik2yvsbx6jj30vck32da2bbvj4m0gf4jhp09vr75i1d6jzfvb";
       type = "gem";
     };
-    version = "1.5.0";
+    version = "1.7.0";
   };
   faraday-em_http = {
     groups = ["default"];
@@ -76,10 +76,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0l2c835wl7gv34xp49fhd1bl4czkpw2g3ahqsak2251iqv5589ka";
+      sha256 = "0dc36ih95qw3rlccffcb0vgxjhmipsvxhn6cw71l7ffs0f7vq30b";
       type = "gem";
     };
-    version = "1.1.0";
+    version = "1.2.0";
   };
   faraday-patron = {
     groups = ["default"];
@@ -91,6 +91,16 @@
     };
     version = "1.0.0";
   };
+  faraday-rack = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1h184g4vqql5jv9s9im6igy00jp6mrah2h14py6mpf9bkabfqq7g";
+      type = "gem";
+    };
+    version = "1.0.0";
+  };
   multipart-post = {
     groups = ["default"];
     platforms = [];
@@ -127,10 +137,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "15wfcqxyfgka05v2a7kpg64x57gl1y4xzvnc9lh60bqx5sf1iqrs";
+      sha256 = "1vz322p8n39hz3b4a9gkmz9y7a5jaz41zrm2ywf31dvkqm03glgz";
       type = "gem";
     };
-    version = "0.0.4";
+    version = "0.0.5";
   };
   sawyer = {
     dependencies = ["addressable" "faraday"];
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/Gemfile b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/Gemfile
new file mode 100644
index 00000000000..0fcdf01d56f
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/Gemfile
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+source "https://rubygems.org"
+
+gem 'bcrypt', '3.1.3'
+gem 'unix-crypt', '1.3.0'
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/Gemfile.lock b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/Gemfile.lock
new file mode 100644
index 00000000000..2c9fb904930
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/Gemfile.lock
@@ -0,0 +1,15 @@
+GEM
+  remote: https://rubygems.org/
+  specs:
+    bcrypt (3.1.3)
+    unix-crypt (1.3.0)
+
+PLATFORMS
+  x86_64-linux
+
+DEPENDENCIES
+  bcrypt (= 3.1.3)
+  unix-crypt (= 1.3.0)
+
+BUNDLED WITH
+   2.2.20
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/default.nix
new file mode 100644
index 00000000000..4c46dfb181e
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/default.nix
@@ -0,0 +1,18 @@
+{ lib, mkDiscoursePlugin, fetchFromGitHub }:
+
+mkDiscoursePlugin {
+  name = "discourse-migratepassword";
+  bundlerEnvArgs.gemdir = ./.;
+  src = fetchFromGitHub {
+    owner = "communiteq";
+    repo = "discourse-migratepassword";
+    rev = "91d6a008de91853becca01846aa4662bd227670e";
+    sha256 = "sha256-aKj0zXyXDnG20qVdhGvn4fwXiBeHFj2pv4bTUP81MP0=";
+  };
+  meta = with lib; {
+    homepage = "https://github.com/communiteq/discourse-migratepassword";
+    maintainers = with maintainers; [ ryantm ];
+    license = licenses.gpl2Only;
+    description = "Support migrated password hashes";
+  };
+}
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/gemset.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/gemset.nix
new file mode 100644
index 00000000000..22b4053bbd4
--- /dev/null
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-migratepassword/gemset.nix
@@ -0,0 +1,22 @@
+{
+  bcrypt = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1d2gqv8vry4ps0asb7nn1z4zxi3mcscy7yrim0npdd294ffyinvj";
+      type = "gem";
+    };
+    version = "3.1.3";
+  };
+  unix-crypt = {
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1wflipsmmicmgvqilp9pml4x19b337kh6p6jgrzqrzpkq2z52gdq";
+      type = "gem";
+    };
+    version = "1.3.0";
+  };
+}
diff --git a/pkgs/servers/web-apps/discourse/plugins/discourse-solved/default.nix b/pkgs/servers/web-apps/discourse/plugins/discourse-solved/default.nix
index 2d451418bdd..c92c5a1016a 100644
--- a/pkgs/servers/web-apps/discourse/plugins/discourse-solved/default.nix
+++ b/pkgs/servers/web-apps/discourse/plugins/discourse-solved/default.nix
@@ -5,8 +5,8 @@ mkDiscoursePlugin {
   src = fetchFromGitHub {
     owner = "discourse";
     repo = "discourse-solved";
-    rev = "b96374bf4ab7e6d5cecb0761918b060a524eb9bf";
-    sha256 = "0zrv70p0wz93akpcj6gpwjkw7az3iz9bx4n2z630kyrlmxdbj32a";
+    rev = "8bf54370200fe9d94541f69339430a7dc1019d62";
+    sha256 = "1sk91h4dilkxm1wpv8zw59wgw860ywwlcgiw2kd23ybdk9n7b3lh";
   };
   meta = with lib; {
     homepage = "https://github.com/discourse/discourse-solved";
diff --git a/pkgs/servers/web-apps/discourse/update.py b/pkgs/servers/web-apps/discourse/update.py
index ae4dadfc3a7..127088dafbf 100755
--- a/pkgs/servers/web-apps/discourse/update.py
+++ b/pkgs/servers/web-apps/discourse/update.py
@@ -12,6 +12,7 @@ import os
 import stat
 import json
 import requests
+import textwrap
 from distutils.version import LooseVersion
 from pathlib import Path
 from typing import Iterable
@@ -77,7 +78,11 @@ def _call_nix_update(pkg, version):
 
 def _nix_eval(expr: str):
     nixpkgs_path = Path(__file__).parent / '../../../../'
-    return json.loads(subprocess.check_output(['nix', 'eval', '--json', f'(with import {nixpkgs_path} {{}}; {expr})'], text=True))
+    try:
+        output = subprocess.check_output(['nix', 'eval', '--json', f'(with import {nixpkgs_path} {{}}; {expr})'], text=True)
+    except subprocess.CalledProcessError:
+        return None
+    return json.loads(output)
 
 
 def _get_current_package_version(pkg: str):
@@ -111,6 +116,18 @@ def _diff_file(filepath: str, old_version: str, new_version: str):
     return
 
 
+def _remove_platforms(rubyenv_dir: Path):
+    for platform in ['arm64-darwin-20', 'x86_64-darwin-18',
+                     'x86_64-darwin-19', 'x86_64-darwin-20',
+                     'x86_64-linux']:
+        with open(rubyenv_dir / 'Gemfile.lock', 'r') as f:
+            for line in f:
+                if platform in line:
+                    subprocess.check_output(
+                        ['bundle', 'lock', '--remove-platform', platform], cwd=rubyenv_dir)
+                    break
+
+
 @click_log.simple_verbosity_option(logger)
 
 
@@ -173,10 +190,7 @@ def update(rev):
             f.write(repo.get_file(fn, rev))
 
     subprocess.check_output(['bundle', 'lock'], cwd=rubyenv_dir)
-    for platform in ['arm64-darwin-20', 'x86_64-darwin-18',
-                     'x86_64-darwin-19', 'x86_64-darwin-20',
-                     'x86_64-linux']:
-        subprocess.check_output(['bundle', 'lock', '--remove-platform', platform], cwd=rubyenv_dir)
+    _remove_platforms(rubyenv_dir)
     subprocess.check_output(['bundix'], cwd=rubyenv_dir)
 
     _call_nix_update('discourse', repo.rev2version(rev))
@@ -187,9 +201,13 @@ def update_plugins():
 
     """
     plugins = [
+        {'name': 'discourse-calendar'},
         {'name': 'discourse-canned-replies'},
+        {'name': 'discourse-checklist'},
+        {'name': 'discourse-data-explorer'},
         {'name': 'discourse-github'},
         {'name': 'discourse-math'},
+        {'name': 'discourse-migratepassword', 'owner': 'discoursehosting'},
         {'name': 'discourse-solved'},
         {'name': 'discourse-spoiler-alert'},
         {'name': 'discourse-yearly-review'},
@@ -202,13 +220,59 @@ def update_plugins():
         repo_name = plugin.get('repo_name') or name
 
         repo = DiscourseRepo(owner=owner, repo=repo_name)
+
+        filename = _nix_eval(f'builtins.unsafeGetAttrPos "src" discourse.plugins.{name}')
+        if filename is None:
+            filename = Path(__file__).parent / 'plugins' / name / 'default.nix'
+            filename.parent.mkdir()
+
+            has_ruby_deps = False
+            for line in repo.get_file('plugin.rb', repo.latest_commit_sha).splitlines():
+                if 'gem ' in line:
+                    has_ruby_deps = True
+                    break
+
+            with open(filename, 'w') as f:
+                f.write(textwrap.dedent(f"""
+                         {{ lib, mkDiscoursePlugin, fetchFromGitHub }}:
+
+                         mkDiscoursePlugin {{
+                           name = "{name}";"""[1:] + ("""
+                           bundlerEnvArgs.gemdir = ./.;""" if has_ruby_deps else "") + f"""
+                           src = {fetcher} {{
+                             owner = "{owner}";
+                             repo = "{repo_name}";
+                             rev = "replace-with-git-rev";
+                             sha256 = "replace-with-sha256";
+                           }};
+                           meta = with lib; {{
+                             homepage = "";
+                             maintainers = with maintainers; [ ];
+                             license = licenses.mit; # change to the correct license!
+                             description = "";
+                           }};
+                         }}"""))
+
+            all_plugins_filename = Path(__file__).parent / 'plugins' / 'all-plugins.nix'
+            with open(all_plugins_filename, 'r+') as f:
+                content = f.read()
+                pos = -1
+                while content[pos] != '}':
+                    pos -= 1
+                content = content[:pos] + f'  {name} = callPackage ./{name} {{}};' + os.linesep + content[pos:]
+                f.seek(0)
+                f.write(content)
+                f.truncate()
+
+        else:
+            filename = filename['file']
+
         prev_commit_sha = _nix_eval(f'discourse.plugins.{name}.src.rev')
 
         if prev_commit_sha == repo.latest_commit_sha:
             click.echo(f'Plugin {name} is already at the latest revision')
             continue
 
-        filename = _nix_eval(f'builtins.unsafeGetAttrPos "src" discourse.plugins.{name}')['file']
         prev_hash = _nix_eval(f'discourse.plugins.{name}.src.outputHash')
         new_hash = subprocess.check_output([
             'nix-universal-prefetch', fetcher,
@@ -244,7 +308,9 @@ def update_plugins():
             with open(gemfile, 'a') as f:
                 f.write(gemfile_text)
 
+            subprocess.check_output(['bundle', 'lock', '--add-platform', 'ruby'], cwd=rubyenv_dir)
             subprocess.check_output(['bundle', 'lock', '--update'], cwd=rubyenv_dir)
+            _remove_platforms(rubyenv_dir)
             subprocess.check_output(['bundix'], cwd=rubyenv_dir)