diff --git a/.circleci/config.yml b/.circleci/config.yml
index 3f158f2..6d5e0d4 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -1,16 +1,4 @@
 ---
-# ---------------------------------------------------------------------------------------------------------------------
-# CircleCI Snippets
-#
-# Reusable snippets are defined below this section. These are yaml fragments that can injected into the standard
-# CircleCI configuration, reducing the complexity of the entire block.
-# ---------------------------------------------------------------------------------------------------------------------
-docker_image: &docker_image
-  image: ${CUSTOMINK_ECR_URL}/customink/base-ruby:2.7-v4.0
-  aws_auth:
-    aws_access_key_id: ${PRODUCTION_AWS_ACCESS_KEY_ID}
-    aws_secret_access_key: ${PRODUCTION_AWS_SECRET_ACCESS_KEY}
-
 # ---------------------------------------------------------------------------------------------------------------------
 # CircleCI Commands Configuration
 #
@@ -20,25 +8,26 @@ docker_image: &docker_image
 # ---------------------------------------------------------------------------------------------------------------------
 version: 2.1
 commands:
-  bundle_install:
-    description: "Performs the bundler installation, relying on the CircleCI cache for performance"
+  appraisal_install:
+    description: "Performs the installation with Appraisal"
+    parameters:
+      ruby-version:
+        type: string
     steps:
       - restore_cache:
           keys:
-            - bundler-cache-{{ checksum "is_it_up.gemspec" }}
+            - appraisal-cache-<< parameters.ruby-version >>-1.0-{{ checksum "is_it_up.gemspec" }}
       - run:
-          name: "Bundle Install"
-          command: bundle install --path=.bundle
+          name: "Appraisal Install"
+          command: |
+            bundle config --local path vendor/bundle
+            bundle install --jobs 4 --retry 3
+            bundle exec appraisal install
       - save_cache:
-          key: bundler-cache-{{ checksum "is_it_up.gemspec" }}
+          key: appraisal-cache-<< parameters.ruby-version >>-1.0-{{ checksum "is_it_up.gemspec" }}
           paths:
-            - .bundle
-  minitest:
-    description: "Runs Minitest with the correct configuration so it runs in parallel and is configured for CircleCI"
-    steps:
-      - run:
-          name: "Minitest Test Suite"
-          command: bundle exec rake
+            - vendor/bundle
+
 # ---------------------------------------------------------------------------------------------------------------------
 # CircleCI Job Configuration
 #
@@ -48,22 +37,67 @@ commands:
 # ---------------------------------------------------------------------------------------------------------------------
 jobs:
   tests:
-    working_directory: ~/is_it_up
+    parameters:
+      ruby-version:
+        type: string
+      gemfile:
+        type: string
     docker:
-      - <<: *docker_image
+      - image: 916869144969.dkr.ecr.us-east-1.amazonaws.com/customink/base-ruby:<< parameters.ruby-version >>-v5.5
+        user: root
+        aws_auth:
+          aws_access_key_id: ${PRODUCTION_AWS_ACCESS_KEY_ID}
+          aws_secret_access_key: ${PRODUCTION_AWS_SECRET_ACCESS_KEY}
         environment:
           RAILS_ENV: test
+          RACK_ENV: test
+    working_directory: "/app"
     steps:
       - checkout
-      - bundle_install
-      - minitest
+      - appraisal_install:
+          ruby-version: << parameters.ruby-version >>
+      - run:
+          name: "Tests"
+          command: bundle exec appraisal << parameters.gemfile >> rake test
+      - store_artifacts:
+          path: ./coverage
       - store_test_results:
-          path: test/reports
+          path: ./test/reports
       - store_artifacts:
-          path: coverage
+          path: ./test/reports
+
+# ---------------------------------------------------------------------------------------------------------------------
+# CircleCI Workflow Execution Order
+#
+# Here we define the Workflow, the order of the various jobs and their dependencies.
+# This allows us to decide whether to run certain tasks sequentially or run several of them in parallel.
+# ---------------------------------------------------------------------------------------------------------------------
 workflows:
   version: 2.1
   build-and-test:
     jobs:
       - tests:
+          name: "Ruby 2.6 Tests with Rails 5.0"
+          context: customink
+          gemfile: "rails5.0"
+          ruby-version: "2.6"
+      - tests:
+          name: "Ruby 2.6 Tests with Rails 5.1"
+          context: customink
+          gemfile: "rails5.1"
+          ruby-version: "2.6"
+      - tests:
+          name: "Ruby 2.6 Tests with Rails 5.2"
+          context: customink
+          gemfile: "rails5.2"
+          ruby-version: "2.6"
+      - tests:
+          name: "Ruby 2.6 Tests with Rails 6.0"
+          context: customink
+          gemfile: "rails6.0"
+          ruby-version: "2.6"
+      - tests:
+          name: "Ruby 2.6 Tests with Rails 6.1"
           context: customink
+          gemfile: "rails6.1"
+          ruby-version: "2.6"
diff --git a/.gitignore b/.gitignore
index 848ea29..8307f3d 100644
--- a/.gitignore
+++ b/.gitignore
@@ -6,6 +6,7 @@
 Gemfile.lock
 InstalledFiles
 _yardoc
+gemfiles/*.gemfile.lock
 coverage
 doc/
 lib/bundler/man
diff --git a/Appraisals b/Appraisals
new file mode 100644
index 0000000..dce333e
--- /dev/null
+++ b/Appraisals
@@ -0,0 +1,30 @@
+# This is the appraisal file that determines which specific gems should be
+# tested in various situations. Because Appraisal was originally developed
+# for the Travis CI system, a few minor tweaks are added to this file,
+# to ensure we can actually run this properly on CircleCI.
+#
+# The core change is that we perform a Ruby version check in this file to
+# exclude certain configurations from specific Ruby machines to simulate
+# the configuration we had in Travis CI where we excluded a specific Gemfile from
+# a build. That feature does not exist in CircleCI, so to ensure that the
+# "bundle exec appraisal install" command works,
+# we exclude certain appraisals when the Ruby version doesn't match.
+appraise 'rails5.0' do
+  gem 'rails', '~> 5.0.0'
+end
+
+appraise 'rails5.1' do
+  gem 'rails', '~> 5.1.0'
+end
+
+appraise 'rails5.2' do
+  gem 'rails', '~> 5.2.0'
+end
+
+appraise 'rails6.0' do
+  gem 'rails', '~> 6.0.0'
+end
+
+appraise 'rails6.1' do
+  gem 'rails', '~> 6.1.0'
+end
diff --git a/CHANGELOG.md b/CHANGELOG.md
index abf1bb7..b5aead1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,10 @@
 # IsItUp Changelog
 
+## 1.0.0
+- Added Appraisal for proper testing against various Rails versions
+- Updated documentation
+- Enforced direct loading of `::Railtie`
+
 ## 0.0.5
 - Fix the autoloading for `Railtie`
 
diff --git a/Gemfile b/Gemfile
index 1220c72..9962304 100644
--- a/Gemfile
+++ b/Gemfile
@@ -4,6 +4,7 @@ source 'https://rubygems.org'
 gemspec
 
 group :test do
+  gem 'appraisal'
   gem 'minitest-ci', require: false
   gem 'simplecov', require: false
 end
diff --git a/gemfiles/rails5.0.gemfile b/gemfiles/rails5.0.gemfile
new file mode 100644
index 0000000..a675b4a
--- /dev/null
+++ b/gemfiles/rails5.0.gemfile
@@ -0,0 +1,13 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "rails", "~> 5.0.0"
+
+group :test do
+  gem "appraisal"
+  gem "minitest-ci", require: false
+  gem "simplecov", require: false
+end
+
+gemspec path: "../"
diff --git a/gemfiles/rails5.1.gemfile b/gemfiles/rails5.1.gemfile
new file mode 100644
index 0000000..a6cef12
--- /dev/null
+++ b/gemfiles/rails5.1.gemfile
@@ -0,0 +1,13 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "rails", "~> 5.1.0"
+
+group :test do
+  gem "appraisal"
+  gem "minitest-ci", require: false
+  gem "simplecov", require: false
+end
+
+gemspec path: "../"
diff --git a/gemfiles/rails5.2.gemfile b/gemfiles/rails5.2.gemfile
new file mode 100644
index 0000000..ff4dc54
--- /dev/null
+++ b/gemfiles/rails5.2.gemfile
@@ -0,0 +1,13 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "rails", "~> 5.2.0"
+
+group :test do
+  gem "appraisal"
+  gem "minitest-ci", require: false
+  gem "simplecov", require: false
+end
+
+gemspec path: "../"
diff --git a/gemfiles/rails6.0.gemfile b/gemfiles/rails6.0.gemfile
new file mode 100644
index 0000000..fbb63ee
--- /dev/null
+++ b/gemfiles/rails6.0.gemfile
@@ -0,0 +1,13 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "rails", "~> 6.0.0"
+
+group :test do
+  gem "appraisal"
+  gem "minitest-ci", require: false
+  gem "simplecov", require: false
+end
+
+gemspec path: "../"
diff --git a/gemfiles/rails6.1.gemfile b/gemfiles/rails6.1.gemfile
new file mode 100644
index 0000000..0323667
--- /dev/null
+++ b/gemfiles/rails6.1.gemfile
@@ -0,0 +1,13 @@
+# This file was generated by Appraisal
+
+source "https://rubygems.org"
+
+gem "rails", "~> 6.1.0"
+
+group :test do
+  gem "appraisal"
+  gem "minitest-ci", require: false
+  gem "simplecov", require: false
+end
+
+gemspec path: "../"
diff --git a/lib/is_it_up.rb b/lib/is_it_up.rb
index ad82d24..924e756 100644
--- a/lib/is_it_up.rb
+++ b/lib/is_it_up.rb
@@ -1,7 +1,12 @@
 require "rack"
 
+# This module defines our Gem, and automatically requires the needed files to ensure that the gem can hook into
+# the application's middleware stack when needed, or triggers the Rails boot process properly using the Railtie
+# framework.
+# Do not swap this code to rely on autoload, since this behavior is not compatible with higher Ruby releases.
+# We need to code to be loaded immediately, and not on-demand as this will be too late for the Rails boot process.
 module IsItUp
-  autoload :VERSION, "is_it_up/version"
-  autoload :Middleware, "is_it_up/middleware"
-  autoload :Railtie, "is_it_up/railtie" if defined?(Rails::Railtie)
+  require_relative 'is_it_up/version'
+  require_relative 'is_it_up/middleware'
+  require_relative 'is_it_up/railtie' if defined?(::Rails::Railtie)
 end
diff --git a/lib/is_it_up/version.rb b/lib/is_it_up/version.rb
index bc95bd3..dd5246d 100644
--- a/lib/is_it_up/version.rb
+++ b/lib/is_it_up/version.rb
@@ -1,3 +1,5 @@
 module IsItUp
-  VERSION = "0.0.5"
+  VERSION = '1.0.0'.freeze
+
+  public_constant :VERSION
 end