diff --git a/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile b/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile
index 9e65ac43afa1..cfeefff2f0a3 100644
--- a/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile
+++ b/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile
@@ -5,6 +5,7 @@ gem 'asciidoctor-diagram'
 gem 'asciidoctor-epub3'
 gem 'asciidoctor-html5s'
 gem 'asciidoctor-mathematical'
+gem 'asciidoctor-multipage'
 gem 'asciidoctor-pdf'
 gem 'asciidoctor-revealjs'
 gem 'asciidoctor-rouge'
diff --git a/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile.lock b/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile.lock
index 98418e183d45..5b0e79aa2bd5 100644
--- a/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile.lock
+++ b/pkgs/tools/typesetting/asciidoctor-with-extensions/Gemfile.lock
@@ -5,7 +5,7 @@ GEM
     addressable (2.8.0)
       public_suffix (>= 2.0.2, < 5.0)
     afm (0.2.2)
-    asciidoctor (2.0.16)
+    asciidoctor (2.0.17)
     asciidoctor-bibtex (0.8.0)
       asciidoctor (~> 2.0)
       bibtex-ruby (~> 5.1)
@@ -30,7 +30,9 @@ GEM
       asciidoctor (~> 2.0)
       asciimath (~> 2.0)
       mathematical (~> 1.6.0)
-    asciidoctor-pdf (1.6.1)
+    asciidoctor-multipage (0.0.15)
+      asciidoctor (>= 2.0.11, < 2.1)
+    asciidoctor-pdf (1.6.2)
       asciidoctor (~> 2.0)
       concurrent-ruby (~> 1.1)
       prawn (~> 2.4.0)
@@ -62,7 +64,7 @@ GEM
       rexml
     csl-styles (1.0.1.11)
       csl (~> 1.0)
-    css_parser (1.10.0)
+    css_parser (1.11.0)
       addressable
     gepub (1.0.15)
       nokogiri (>= 1.8.2, < 2.0)
@@ -75,14 +77,14 @@ GEM
       ruby-enum (~> 0.4)
     mime-types (3.4.1)
       mime-types-data (~> 3.2015)
-    mime-types-data (3.2021.1115)
-    mini_portile2 (2.6.1)
+    mime-types-data (3.2022.0105)
+    mini_portile2 (2.7.1)
     namae (1.1.1)
-    nokogiri (1.12.5)
-      mini_portile2 (~> 2.6.1)
+    nokogiri (1.13.1)
+      mini_portile2 (~> 2.7.0)
       racc (~> 1.4)
     pdf-core (0.9.0)
-    pdf-reader (2.6.0)
+    pdf-reader (2.8.0)
       Ascii85 (~> 1.0)
       afm (~> 0.2.1)
       hashery (~> 2.0)
@@ -104,10 +106,10 @@ GEM
       pdf-reader (~> 2.0)
       prawn (~> 2.2)
     public_suffix (4.0.6)
-    pygments.rb (2.2.0)
+    pygments.rb (2.3.0)
     racc (1.6.0)
     rexml (3.2.5)
-    rouge (3.26.1)
+    rouge (3.27.0)
     ruby-enum (0.9.0)
       i18n
     ruby-rc4 (0.1.5)
@@ -128,6 +130,7 @@ DEPENDENCIES
   asciidoctor-epub3
   asciidoctor-html5s
   asciidoctor-mathematical
+  asciidoctor-multipage
   asciidoctor-pdf
   asciidoctor-revealjs
   asciidoctor-rouge
diff --git a/pkgs/tools/typesetting/asciidoctor-with-extensions/default.nix b/pkgs/tools/typesetting/asciidoctor-with-extensions/default.nix
index 6bb0eac62f12..c4aa7fa4a271 100644
--- a/pkgs/tools/typesetting/asciidoctor-with-extensions/default.nix
+++ b/pkgs/tools/typesetting/asciidoctor-with-extensions/default.nix
@@ -10,8 +10,9 @@ bundlerApp {
 
   exes = [
     "asciidoctor"
-    "asciidoctor-pdf"
     "asciidoctor-epub3"
+    "asciidoctor-multipage"
+    "asciidoctor-pdf"
     "asciidoctor-revealjs"
   ];
 
diff --git a/pkgs/tools/typesetting/asciidoctor-with-extensions/gemset.nix b/pkgs/tools/typesetting/asciidoctor-with-extensions/gemset.nix
index e88f9701d0d3..498653c12f2e 100644
--- a/pkgs/tools/typesetting/asciidoctor-with-extensions/gemset.nix
+++ b/pkgs/tools/typesetting/asciidoctor-with-extensions/gemset.nix
@@ -35,10 +35,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "10h4pmmkbcrpy7bn76wxzkb0hriabh1k3ii1g8lm0mdji5drlhq2";
+      sha256 = "0g8gn3g6qy4bzjv1b14sj283kqynjgwq62bgq569jr4dkqwmwnzd";
       type = "gem";
     };
-    version = "2.0.16";
+    version = "2.0.17";
   };
   asciidoctor-bibtex = {
     dependencies = ["asciidoctor" "bibtex-ruby" "citeproc-ruby" "csl-styles" "latex-decode"];
@@ -115,16 +115,27 @@
     };
     version = "0.3.5";
   };
+  asciidoctor-multipage = {
+    dependencies = ["asciidoctor"];
+    groups = ["default"];
+    platforms = [];
+    source = {
+      remotes = ["https://rubygems.org"];
+      sha256 = "1372213kxw1b9k120dmyackafzsk80h1y2n0r1hmfrri26kczgfb";
+      type = "gem";
+    };
+    version = "0.0.15";
+  };
   asciidoctor-pdf = {
     dependencies = ["asciidoctor" "concurrent-ruby" "prawn" "prawn-icon" "prawn-svg" "prawn-table" "prawn-templates" "safe_yaml" "treetop"];
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "17d3fa6ix6r5ikydqz41r620mm98s076wdg4w6ydsr655r7mvnpk";
+      sha256 = "1inl7cykm542jb7a6kraxkgfqn4y3185wrabh5pd5m68rdv56f04";
       type = "gem";
     };
-    version = "1.6.1";
+    version = "1.6.2";
   };
   asciidoctor-revealjs = {
     dependencies = ["asciidoctor" "concurrent-ruby" "thread_safe"];
@@ -239,10 +250,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1q8gj3wkc2mbzsqw5zcsr3kyzrrb2pda03pi769rjbvqr94g3bm5";
+      sha256 = "1qbdgp36dhcyljhmfxrvbgp1ha9yqxhxgyg3sdm48y9m371jd2an";
       type = "gem";
     };
-    version = "1.10.0";
+    version = "1.11.0";
   };
   gepub = {
     dependencies = ["nokogiri" "rubyzip"];
@@ -313,20 +324,20 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "03m3fkix2haah20kvh1jgv262yg9jlzn6wq0y31kafxk8fysfy27";
+      sha256 = "003gd7mcay800k2q4pb2zn8lwwgci4bhi42v2jvlidm8ksx03i6q";
       type = "gem";
     };
-    version = "3.2021.1115";
+    version = "3.2022.0105";
   };
   mini_portile2 = {
     groups = ["default"];
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1lvxm91hi0pabnkkg47wh1siv56s6slm2mdq1idfm86dyfidfprq";
+      sha256 = "0d3ga166pahsxavzwj19yjj4lr13rw1vsb36s2qs8blcxigrdp6z";
       type = "gem";
     };
-    version = "2.6.1";
+    version = "2.7.1";
   };
   namae = {
     groups = ["default"];
@@ -344,10 +355,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1v02g7k7cxiwdcahvlxrmizn3avj2q6nsjccgilq1idc89cr081b";
+      sha256 = "1zqzawia52cdcmi55lp7v8jmiqyw7pcpwsksqlnirwfm3f7bnf11";
       type = "gem";
     };
-    version = "1.12.5";
+    version = "1.13.1";
   };
   pdf-core = {
     groups = ["default"];
@@ -365,10 +376,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0zgv9pp9cqd1cf8bwk7pb5lkm81gn7znnan0a7s42wd0qavs4nnz";
+      sha256 = "18vsmybpvyi0favlabjipznpc8hgprsm7jpw3s7xr01c3lpjli7y";
       type = "gem";
     };
-    version = "2.6.0";
+    version = "2.8.0";
   };
   polyglot = {
     groups = ["default"];
@@ -450,10 +461,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1mshqjh8v0v8k29f8annqfr4qlgkp39nbwx3sgm69aymv4skfddb";
+      sha256 = "047mjyzz8v4kkgi1ap6fsjf7kcp6dwirpnigif00ss0hxsxchhac";
       type = "gem";
     };
-    version = "2.2.0";
+    version = "2.3.0";
   };
   racc = {
     groups = ["default"];
@@ -480,10 +491,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "197k0vskf72wxx0gzwld2jzg27bb7982xlvnzy9adlvkzp7nh8vf";
+      sha256 = "0530ri0p60km0bg0ib6swkhfnas427cva7vcdmnwl8df52a10y1k";
       type = "gem";
     };
-    version = "3.26.1";
+    version = "3.27.0";
   };
   ruby-enum = {
     dependencies = ["i18n"];
diff --git a/pkgs/tools/typesetting/asciidoctor/Gemfile.lock b/pkgs/tools/typesetting/asciidoctor/Gemfile.lock
index 5c607d269b22..7652239b998d 100644
--- a/pkgs/tools/typesetting/asciidoctor/Gemfile.lock
+++ b/pkgs/tools/typesetting/asciidoctor/Gemfile.lock
@@ -5,8 +5,8 @@ GEM
     addressable (2.8.0)
       public_suffix (>= 2.0.2, < 5.0)
     afm (0.2.2)
-    asciidoctor (2.0.16)
-    asciidoctor-pdf (1.6.1)
+    asciidoctor (2.0.17)
+    asciidoctor-pdf (1.6.2)
       asciidoctor (~> 2.0)
       concurrent-ruby (~> 1.1)
       prawn (~> 2.4.0)
@@ -18,11 +18,11 @@ GEM
       treetop (~> 1.6.0)
     coderay (1.1.3)
     concurrent-ruby (1.1.9)
-    css_parser (1.10.0)
+    css_parser (1.11.0)
       addressable
     hashery (2.1.2)
     pdf-core (0.9.0)
-    pdf-reader (2.6.0)
+    pdf-reader (2.8.0)
       Ascii85 (~> 1.0)
       afm (~> 0.2.1)
       hashery (~> 2.0)
@@ -44,9 +44,9 @@ GEM
       pdf-reader (~> 2.0)
       prawn (~> 2.2)
     public_suffix (4.0.6)
-    pygments.rb (2.2.0)
+    pygments.rb (2.3.0)
     rexml (3.2.5)
-    rouge (3.26.1)
+    rouge (3.27.0)
     ruby-rc4 (0.1.5)
     safe_yaml (1.0.5)
     treetop (1.6.11)
diff --git a/pkgs/tools/typesetting/asciidoctor/gemset.nix b/pkgs/tools/typesetting/asciidoctor/gemset.nix
index b57d1e5ac4ad..d87c6c1fa995 100644
--- a/pkgs/tools/typesetting/asciidoctor/gemset.nix
+++ b/pkgs/tools/typesetting/asciidoctor/gemset.nix
@@ -35,10 +35,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "10h4pmmkbcrpy7bn76wxzkb0hriabh1k3ii1g8lm0mdji5drlhq2";
+      sha256 = "0g8gn3g6qy4bzjv1b14sj283kqynjgwq62bgq569jr4dkqwmwnzd";
       type = "gem";
     };
-    version = "2.0.16";
+    version = "2.0.17";
   };
   asciidoctor-pdf = {
     dependencies = ["asciidoctor" "concurrent-ruby" "prawn" "prawn-icon" "prawn-svg" "prawn-table" "prawn-templates" "safe_yaml" "treetop"];
@@ -46,10 +46,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "17d3fa6ix6r5ikydqz41r620mm98s076wdg4w6ydsr655r7mvnpk";
+      sha256 = "1inl7cykm542jb7a6kraxkgfqn4y3185wrabh5pd5m68rdv56f04";
       type = "gem";
     };
-    version = "1.6.1";
+    version = "1.6.2";
   };
   coderay = {
     groups = ["default"];
@@ -77,10 +77,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1q8gj3wkc2mbzsqw5zcsr3kyzrrb2pda03pi769rjbvqr94g3bm5";
+      sha256 = "1qbdgp36dhcyljhmfxrvbgp1ha9yqxhxgyg3sdm48y9m371jd2an";
       type = "gem";
     };
-    version = "1.10.0";
+    version = "1.11.0";
   };
   hashery = {
     groups = ["default"];
@@ -108,10 +108,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "0zgv9pp9cqd1cf8bwk7pb5lkm81gn7znnan0a7s42wd0qavs4nnz";
+      sha256 = "18vsmybpvyi0favlabjipznpc8hgprsm7jpw3s7xr01c3lpjli7y";
       type = "gem";
     };
-    version = "2.6.0";
+    version = "2.8.0";
   };
   polyglot = {
     groups = ["default"];
@@ -193,10 +193,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "1mshqjh8v0v8k29f8annqfr4qlgkp39nbwx3sgm69aymv4skfddb";
+      sha256 = "047mjyzz8v4kkgi1ap6fsjf7kcp6dwirpnigif00ss0hxsxchhac";
       type = "gem";
     };
-    version = "2.2.0";
+    version = "2.3.0";
   };
   rexml = {
     groups = ["default"];
@@ -213,10 +213,10 @@
     platforms = [];
     source = {
       remotes = ["https://rubygems.org"];
-      sha256 = "197k0vskf72wxx0gzwld2jzg27bb7982xlvnzy9adlvkzp7nh8vf";
+      sha256 = "0530ri0p60km0bg0ib6swkhfnas427cva7vcdmnwl8df52a10y1k";
       type = "gem";
     };
-    version = "3.26.1";
+    version = "3.27.0";
   };
   ruby-rc4 = {
     groups = ["default"];