diff --git a/.ruby-version b/.ruby-version
index 530cdd91..b0f6bf0c 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.2.4
+2.4.10
diff --git a/Gemfile b/Gemfile
index 2dfa6bac..4504ecde 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,7 +1,7 @@
 source 'http://rubygems.org'
-ruby '2.2.4'
+ruby '2.4.10'
 
-gem 'rails', '= 4.1.16'
+gem 'rails', '= 4.2.11.3'
 
 # Our database is MySQL, in both development and production.
 gem 'mysql2', '>= 0.3.11'
@@ -21,7 +21,7 @@ gem 'react-rails', '~> 2.7', '>= 2.7.1'
 gem 'will_paginate', '~> 3.0.pre2'
 
 # For authentication.
-gem 'devise', '~> 3.5.10'
+gem 'devise', '~> 4.9', '>= 4.9.2'
 
 # For translation, both for the site UI and for Neopets data.
 gem 'rails-i18n', '~> 4.0', '>= 4.0.9'
@@ -29,7 +29,7 @@ gem 'http_accept_language', '~> 2.1', '>= 2.1.1'
 gem 'globalize', '~> 4.0.3'
 
 # For reading and parsing HTML from Neopets.com, like importing Closet pages.
-gem "nokogiri", "~> 1.5.2"
+gem 'nokogiri', '~> 1.10', '>= 1.10.10'
 gem "rest-client", "~> 1.6.7"
 
 # For safely rendering users' Markdown + HTML on item list pages.
@@ -41,7 +41,7 @@ gem 'sanitize', '~> 2.0.3'
 gem 'RocketAMF', :git => 'https://github.com/rubyamf/rocketamf.git'
 
 # For working with the OpenNeo ID service.
-gem 'msgpack', '~> 0.5.3'
+gem 'msgpack', '~> 1.6', '>= 1.6.1'
 gem 'openneo-auth-signatory', '~> 0.1.0'
 
 # For preventing too many modeling attempts.
@@ -53,6 +53,14 @@ gem "letter_opener", :group => :development
 # For parallel API calls.
 gem "parallel", "~> 1.13.0"
 
+# TODO: Rails requests the latest version of these dependencies, but they
+# require Ruby 2.5 or higher, so we have to request lower ones instead!
+# (loofah is slightly trickier: it requires a recent nokogiri, but recent
+# nokogiri requires Ruby 2.6, so, yeah.)
+gem 'loofah', '~> 2.20', '< 2.21'
+gem 'minitest', '~> 5.15', '< 5.16'
+gem 'mail', '~> 2.7', '>= 2.7.1', '< 2.8'
+
 # For deployment.
 group :development do
   gem 'capistrano', '~> 2.15.5', require: false
@@ -66,6 +74,6 @@ end
 
 # For testing.
 group :test do
-  gem 'factory_girl_rails', '~> 1.0'
+  gem 'factory_girl_rails', '~> 4.9'
   gem 'rspec-rails', '~> 2.0.0.beta.22'
 end
diff --git a/Gemfile.lock b/Gemfile.lock
index 98619c40..23cbc0c7 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -7,34 +7,42 @@ GIT
 GEM
   remote: http://rubygems.org/
   specs:
-    actionmailer (4.1.16)
-      actionpack (= 4.1.16)
-      actionview (= 4.1.16)
+    actionmailer (4.2.11.3)
+      actionpack (= 4.2.11.3)
+      actionview (= 4.2.11.3)
+      activejob (= 4.2.11.3)
       mail (~> 2.5, >= 2.5.4)
-    actionpack (4.1.16)
-      actionview (= 4.1.16)
-      activesupport (= 4.1.16)
-      rack (~> 1.5.2)
+      rails-dom-testing (~> 1.0, >= 1.0.5)
+    actionpack (4.2.11.3)
+      actionview (= 4.2.11.3)
+      activesupport (= 4.2.11.3)
+      rack (~> 1.6)
       rack-test (~> 0.6.2)
-    actionview (4.1.16)
-      activesupport (= 4.1.16)
+      rails-dom-testing (~> 1.0, >= 1.0.5)
+      rails-html-sanitizer (~> 1.0, >= 1.0.2)
+    actionview (4.2.11.3)
+      activesupport (= 4.2.11.3)
       builder (~> 3.1)
       erubis (~> 2.7.0)
-    activemodel (4.1.16)
-      activesupport (= 4.1.16)
+      rails-dom-testing (~> 1.0, >= 1.0.5)
+      rails-html-sanitizer (~> 1.0, >= 1.0.3)
+    activejob (4.2.11.3)
+      activesupport (= 4.2.11.3)
+      globalid (>= 0.3.0)
+    activemodel (4.2.11.3)
+      activesupport (= 4.2.11.3)
       builder (~> 3.1)
-    activerecord (4.1.16)
-      activemodel (= 4.1.16)
-      activesupport (= 4.1.16)
-      arel (~> 5.0.0)
-    activesupport (4.1.16)
-      i18n (~> 0.6, >= 0.6.9)
-      json (~> 1.7, >= 1.7.7)
+    activerecord (4.2.11.3)
+      activemodel (= 4.2.11.3)
+      activesupport (= 4.2.11.3)
+      arel (~> 6.0)
+    activesupport (4.2.11.3)
+      i18n (~> 0.7)
       minitest (~> 5.1)
-      thread_safe (~> 0.1)
+      thread_safe (~> 0.3, >= 0.3.4)
       tzinfo (~> 1.1)
     addressable (2.3.8)
-    arel (5.0.1.20140414130214)
+    arel (6.0.4)
     babel-source (5.8.35)
     babel-transpiler (0.7.0)
       babel-source (>= 4.0, < 6)
@@ -64,14 +72,14 @@ GEM
       compass (~> 1.0.0)
       sass-rails (< 5.1)
       sprockets (< 4.0)
-    concurrent-ruby (1.1.10)
+    concurrent-ruby (1.2.2)
     connection_pool (2.2.5)
-    devise (3.5.10)
+    crass (1.0.6)
+    devise (4.9.2)
       bcrypt (~> 3.0)
       orm_adapter (~> 0.1)
-      railties (>= 3.2.6, < 5)
+      railties (>= 4.1.0)
       responders
-      thread_safe (~> 0.1)
       warden (~> 1.2.3)
     diff-lcs (1.2.5)
     dotenv (2.8.1)
@@ -80,12 +88,14 @@ GEM
       railties (>= 3.2)
     erubis (2.7.0)
     execjs (2.5.2)
-    factory_girl (2.6.4)
-      activesupport (>= 2.3.9)
-    factory_girl_rails (1.7.0)
-      factory_girl (~> 2.6.0)
+    factory_girl (4.9.0)
+      activesupport (>= 3.0.0)
+    factory_girl_rails (4.9.0)
+      factory_girl (~> 4.9.0)
       railties (>= 3.0.0)
     ffi (1.12.2)
+    globalid (0.4.2)
+      activesupport (>= 4.2.0)
     globalize (4.0.3)
       activemodel (>= 4.0.0, < 5)
       activerecord (>= 4.0.0, < 5)
@@ -97,18 +107,21 @@ GEM
     http_accept_language (2.1.1)
     i18n (0.9.5)
       concurrent-ruby (~> 1.0)
-    json (1.8.6)
     launchy (2.4.3)
       addressable (~> 2.3)
     letter_opener (1.4.1)
       launchy (~> 2.2)
+    loofah (2.20.0)
+      crass (~> 1.0.2)
+      nokogiri (>= 1.5.9)
     mail (2.7.1)
       mini_mime (>= 0.1.1)
     memcache-client (1.8.5)
     mime-types (1.25.1)
     mini_mime (1.1.2)
+    mini_portile2 (2.4.0)
     minitest (5.15.0)
-    msgpack (0.5.12)
+    msgpack (1.6.1)
     multi_json (1.15.0)
     mysql2 (0.3.18)
     net-scp (1.0.4)
@@ -118,32 +131,42 @@ GEM
     net-ssh (2.9.2)
     net-ssh-gateway (1.2.0)
       net-ssh (>= 2.6.5)
-    nokogiri (1.5.11)
+    nokogiri (1.10.10)
+      mini_portile2 (~> 2.4.0)
     openneo-auth-signatory (0.1.0)
       ruby-hmac
     orm_adapter (0.5.0)
     parallel (1.13.0)
-    rack (1.5.5)
+    rack (1.6.13)
     rack-attack (2.2.1)
       rack
     rack-test (0.6.3)
       rack (>= 1.0)
-    rails (4.1.16)
-      actionmailer (= 4.1.16)
-      actionpack (= 4.1.16)
-      actionview (= 4.1.16)
-      activemodel (= 4.1.16)
-      activerecord (= 4.1.16)
-      activesupport (= 4.1.16)
+    rails (4.2.11.3)
+      actionmailer (= 4.2.11.3)
+      actionpack (= 4.2.11.3)
+      actionview (= 4.2.11.3)
+      activejob (= 4.2.11.3)
+      activemodel (= 4.2.11.3)
+      activerecord (= 4.2.11.3)
+      activesupport (= 4.2.11.3)
       bundler (>= 1.3.0, < 2.0)
-      railties (= 4.1.16)
-      sprockets-rails (~> 2.0)
+      railties (= 4.2.11.3)
+      sprockets-rails
+    rails-deprecated_sanitizer (1.0.4)
+      activesupport (>= 4.2.0.alpha)
+    rails-dom-testing (1.0.9)
+      activesupport (>= 4.2.0, < 5.0)
+      nokogiri (~> 1.6)
+      rails-deprecated_sanitizer (>= 1.0.1)
+    rails-html-sanitizer (1.5.0)
+      loofah (~> 2.19, >= 2.19.1)
     rails-i18n (4.0.9)
       i18n (~> 0.7)
       railties (~> 4.0)
-    railties (4.1.16)
-      actionpack (= 4.1.16)
-      activesupport (= 4.1.16)
+    railties (4.2.11.3)
+      actionpack (= 4.2.11.3)
+      activesupport (= 4.2.11.3)
       rake (>= 0.8.7)
       thor (>= 0.18.1, < 2.0)
     rake (13.0.6)
@@ -157,8 +180,9 @@ GEM
       execjs
       railties (>= 3.2)
       tilt
-    responders (1.1.2)
-      railties (>= 3.2, < 4.2)
+    responders (2.4.1)
+      actionpack (>= 4.2.0, < 6.0)
+      railties (>= 4.2.0, < 6.0)
     rest-client (1.6.9)
       mime-types (~> 1.16)
     rspec (2.0.1)
@@ -188,10 +212,10 @@ GEM
     sprockets (3.7.2)
       concurrent-ruby (~> 1.0)
       rack (> 1, < 3)
-    sprockets-rails (2.3.3)
-      actionpack (>= 3.0)
-      activesupport (>= 3.0)
-      sprockets (>= 2.8, < 4.0)
+    sprockets-rails (3.2.2)
+      actionpack (>= 4.0)
+      activesupport (>= 4.0)
+      sprockets (>= 3.0.0)
     temple (0.8.2)
     thor (1.2.2)
     thread_safe (0.3.6)
@@ -211,21 +235,24 @@ DEPENDENCIES
   RocketAMF!
   capistrano (~> 2.15.5)
   compass-rails (~> 3.1)
-  devise (~> 3.5.10)
+  devise (~> 4.9, >= 4.9.2)
   dotenv-rails (~> 2.8, >= 2.8.1)
-  factory_girl_rails (~> 1.0)
+  factory_girl_rails (~> 4.9)
   globalize (~> 4.0.3)
   haml (~> 6.1, >= 6.1.1)
   http_accept_language (~> 2.1, >= 2.1.1)
   letter_opener
+  loofah (~> 2.20, < 2.21)
+  mail (~> 2.7, >= 2.7.1, < 2.8)
   memcache-client (~> 1.8.5)
-  msgpack (~> 0.5.3)
+  minitest (~> 5.15, < 5.16)
+  msgpack (~> 1.6, >= 1.6.1)
   mysql2 (>= 0.3.11)
-  nokogiri (~> 1.5.2)
+  nokogiri (~> 1.10, >= 1.10.10)
   openneo-auth-signatory (~> 0.1.0)
   parallel (~> 1.13.0)
   rack-attack (~> 2.2.0)
-  rails (= 4.1.16)
+  rails (= 4.2.11.3)
   rails-i18n (~> 4.0, >= 4.0.9)
   rdiscount (~> 1.6.5)
   react-rails (~> 2.7, >= 2.7.1)
@@ -238,7 +265,7 @@ DEPENDENCIES
   will_paginate (~> 3.0.pre2)
 
 RUBY VERSION
-   ruby 2.2.4p230
+   ruby 2.4.10p364
 
 BUNDLED WITH
    1.17.3
diff --git a/Vagrantfile b/Vagrantfile
index 45636ea1..ed21a91d 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -72,8 +72,10 @@ Vagrant.configure("2") do |config|
   # documentation for more information about their specific syntax and use.
   config.vm.provision "shell", inline: <<-SHELL
     apt-get update
-    apt-get install -y rbenv libmysqlclient-dev libcurl4-openssl-dev nodejs
-    su vagrant -c 'rbenv install 2.2.4 && gem install bundler -v 1.17.3'
+    apt-get install -y libmysqlclient-dev libcurl4-openssl-dev nodejs
+    su vagrant -c 'git clone https://github.com/rbenv/rbenv.git ~/.rbenv'
+    su vagrant -c 'git clone https://github.com/rbenv/ruby-build.git ~/.rbenv/plugins/ruby-build'
+    su vagrant -c '~/.rbenv/bin/rbenv install 2.4.10 && ~/.rbenv/shims/gem install bundler -v 1.17.3'
     apt-get install -y mysql-server
     mysql -e "CREATE USER IF NOT EXISTS openneo_impress IDENTIFIED BY 'openneo_impress';"
     mysql -e "CREATE DATABASE IF NOT EXISTS openneo_impress;"
diff --git a/app/models/swf_asset.rb b/app/models/swf_asset.rb
index d3d99de9..ca1d9677 100644
--- a/app/models/swf_asset.rb
+++ b/app/models/swf_asset.rb
@@ -1,6 +1,5 @@
 require 'fileutils'
 require 'uri'
-require 'encoding/character/utf-8'
 
 class SwfAsset < ActiveRecord::Base
   # We use the `type` column to mean something other than what Rails means!
diff --git a/lib/openneo-auth/session.rb b/lib/openneo-auth/session.rb
index ba712979..0b8011b8 100644
--- a/lib/openneo-auth/session.rb
+++ b/lib/openneo-auth/session.rb
@@ -1,7 +1,6 @@
 require 'active_support/core_ext/hash'
 require 'msgpack'
 require 'openneo-auth-signatory'
-require 'encoding/character/utf-8'
 
 module Openneo
   module Auth
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