diff --git a/.rubocop.common.yml b/.rubocop.common.yml
index 21c0ba541d9..0429015b6b3 100644
--- a/.rubocop.common.yml
+++ b/.rubocop.common.yml
@@ -14,8 +14,12 @@ AllCops:
 Bundler/OrderedGems:
   Enabled: false # this isn't good for us because of how we pin dependencies
 
-Gemspec/OrderedDependencies:
-  Enabled: false # this isn't good for us because of how we pin dependencies
+Gemspec/RequiredRubyVersion:
+  # all the gemspecs in this repo are non-published gems
+  # the root Gemfile enforces the Ruby version, and we purposely
+  # don't specify required_ruby_version in the rest to reduce
+  # maintenance pain when updating ruby versions
+  Enabled: false
 
 Layout/EmptyLineAfterMagicComment:
   Exclude:
diff --git a/.rubocop.enforced.yml b/.rubocop.enforced.yml
index f16b95cbb40..d6996016fd3 100644
--- a/.rubocop.enforced.yml
+++ b/.rubocop.enforced.yml
@@ -16,6 +16,8 @@ AllCops:
 # values are an array of directories to opt in for (nil being all directories)
 OPT_IN = {
   nil => %w[Gemfile.d].freeze,
+  'Bundler' => nil,
+  'Gemspec' => nil,
   'Layout' => %w[bin build config db doc engines gems script].freeze
 }.freeze
 
diff --git a/engines/audits/audits.gemspec b/engines/audits/audits.gemspec
index 0b8bc3611a3..c2c6114b26a 100644
--- a/engines/audits/audits.gemspec
+++ b/engines/audits/audits.gemspec
@@ -15,14 +15,14 @@ Gem::Specification.new do |spec|
   spec.description = "append-only log of important changes within canvas"
   spec.files = Dir["{app,config,db,lib}/**/*", "Rakefile", "README.md"]
 
-  spec.add_dependency "rails", ">= 5.2.4.5"
-  spec.add_dependency "switchman", '>= 2.0.3'
   spec.add_dependency "canvas_cassandra"
   spec.add_dependency "dynamic_settings"
   spec.add_dependency "event_stream"
+  spec.add_dependency "rails", ">= 5.2.4.5"
+  spec.add_dependency "switchman", '>= 2.0.3'
 
-  spec.add_development_dependency "pg"
-  spec.add_development_dependency "rspec-rails"
   spec.add_development_dependency "brakeman"
   spec.add_development_dependency "byebug"
+  spec.add_development_dependency "pg"
+  spec.add_development_dependency "rspec-rails"
 end
diff --git a/gems/acts_as_list/acts_as_list.gemspec b/gems/acts_as_list/acts_as_list.gemspec
index 6bc5bdfcc89..da815710aec 100644
--- a/gems/acts_as_list/acts_as_list.gemspec
+++ b/gems/acts_as_list/acts_as_list.gemspec
@@ -21,6 +21,6 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'rails', ">= 3.2"
 
   spec.add_development_dependency "bundler", ">= 1.5", "< 3.0"
-  spec.add_development_dependency "sqlite3"
   spec.add_development_dependency "rspec", "~> 3.5.0"
+  spec.add_development_dependency "sqlite3"
 end
diff --git a/gems/autoextend/autoextend.gemspec b/gems/autoextend/autoextend.gemspec
index 3c375f78a4f..78f1bd8b6de 100644
--- a/gems/autoextend/autoextend.gemspec
+++ b/gems/autoextend/autoextend.gemspec
@@ -17,7 +17,7 @@ Gem::Specification.new do |spec|
 
   spec.required_ruby_version = '>= 2.0'
 
-  spec.add_development_dependency "byebug"
   spec.add_development_dependency "activesupport"
+  spec.add_development_dependency "byebug"
   spec.add_development_dependency "rspec", "~> 3.5.0"
 end
diff --git a/gems/bookmarked_collection/bookmarked_collection.gemspec b/gems/bookmarked_collection/bookmarked_collection.gemspec
index c22039a956f..d3a9121402f 100644
--- a/gems/bookmarked_collection/bookmarked_collection.gemspec
+++ b/gems/bookmarked_collection/bookmarked_collection.gemspec
@@ -17,15 +17,15 @@ Gem::Specification.new do |spec|
   spec.require_paths = ["lib"]
 
   spec.add_dependency "folio-pagination", "~> 0.0.12"
-  spec.add_dependency "will_paginate", "~> 3.0"
   spec.add_dependency "rails", ">= 3.2"
+  spec.add_dependency "will_paginate", "~> 3.0"
 
-  spec.add_dependency "paginated_collection"
   spec.add_dependency "json_token"
+  spec.add_dependency "paginated_collection"
 
   spec.add_development_dependency "bundler", "~> 2.2"
+  spec.add_development_dependency "byebug"
   spec.add_development_dependency "rake"
   spec.add_development_dependency "rspec", "~> 3.5.0"
   spec.add_development_dependency "sqlite3"
-  spec.add_development_dependency "byebug"
 end
diff --git a/gems/broadcast_policy/broadcast_policy.gemspec b/gems/broadcast_policy/broadcast_policy.gemspec
index 94c27d22973..b4d03843f3c 100644
--- a/gems/broadcast_policy/broadcast_policy.gemspec
+++ b/gems/broadcast_policy/broadcast_policy.gemspec
@@ -19,7 +19,7 @@ Gem::Specification.new do |s|
 
   s.add_dependency "activesupport"
   s.add_dependency "after_transaction_commit"
-  s.add_development_dependency "rspec", "~> 3.5.0"
   s.add_development_dependency "byebug"
   s.add_development_dependency "pry"
+  s.add_development_dependency "rspec", "~> 3.5.0"
 end
diff --git a/gems/canvas_cache/canvas_cache.gemspec b/gems/canvas_cache/canvas_cache.gemspec
index e41abc0a471..e5e8010649a 100644
--- a/gems/canvas_cache/canvas_cache.gemspec
+++ b/gems/canvas_cache/canvas_cache.gemspec
@@ -20,15 +20,15 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'rails'
 
   # redis things required in canvas
+  spec.add_dependency 'digest-murmurhash', '>= 1.1.0'
   spec.add_dependency 'redis', '>= 4.1.0'
   spec.add_dependency 'redis-scripting', '>= 1.0.0'
-  spec.add_dependency 'digest-murmurhash', '>= 1.1.0'
 
   spec.add_dependency 'guardrail', '>= 2.0.0'
   spec.add_dependency 'inst_statsd', '>= 2.1.0'
 
   spec.add_development_dependency 'bundler'
-  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'byebug'
+  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'timecop'
 end
diff --git a/gems/canvas_cassandra/canvas_cassandra.gemspec b/gems/canvas_cassandra/canvas_cassandra.gemspec
index 6de32cb478c..47d2d0b5dbf 100644
--- a/gems/canvas_cassandra/canvas_cassandra.gemspec
+++ b/gems/canvas_cassandra/canvas_cassandra.gemspec
@@ -19,11 +19,11 @@ Gem::Specification.new do |spec|
   spec.require_paths = ["lib"]
 
   spec.add_dependency 'cassandra-cql', '~> 1.2.2'
-  spec.add_dependency "rails", ">= 5.0"
   spec.add_dependency "config_file"
+  spec.add_dependency "rails", ">= 5.0"
 
   spec.add_development_dependency "bundler", "~> 2.2"
+  spec.add_development_dependency "byebug"
   spec.add_development_dependency "rake"
   spec.add_development_dependency "rspec", "~> 3.5.0"
-  spec.add_development_dependency "byebug"
 end
diff --git a/gems/canvas_dynamodb/canvas_dynamodb.gemspec b/gems/canvas_dynamodb/canvas_dynamodb.gemspec
index 5538fc9bcda..1f457d20c6e 100644
--- a/gems/canvas_dynamodb/canvas_dynamodb.gemspec
+++ b/gems/canvas_dynamodb/canvas_dynamodb.gemspec
@@ -18,8 +18,8 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_runtime_dependency 'aws-sdk-dynamodb', '~> 1.32'
   spec.add_runtime_dependency 'aws-sdk-applicationautoscaling', '~> 1.26'
+  spec.add_runtime_dependency 'aws-sdk-dynamodb', '~> 1.32'
 
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "rake"
diff --git a/gems/canvas_errors/canvas_errors.gemspec b/gems/canvas_errors/canvas_errors.gemspec
index 66d673c4eb9..6c4d608e898 100644
--- a/gems/canvas_errors/canvas_errors.gemspec
+++ b/gems/canvas_errors/canvas_errors.gemspec
@@ -20,6 +20,6 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'inst-jobs'
 
   spec.add_development_dependency 'bundler'
-  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'byebug'
+  spec.add_development_dependency 'rspec'
 end
diff --git a/gems/canvas_ext/canvas_ext.gemspec b/gems/canvas_ext/canvas_ext.gemspec
index 83b83690c90..37e548489bb 100644
--- a/gems/canvas_ext/canvas_ext.gemspec
+++ b/gems/canvas_ext/canvas_ext.gemspec
@@ -16,8 +16,8 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_dependency "tzinfo"
   spec.add_dependency "activesupport", ">= 3.2"
+  spec.add_dependency "tzinfo"
 
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "rake"
diff --git a/gems/canvas_http/canvas_http.gemspec b/gems/canvas_http/canvas_http.gemspec
index 77adf28c62f..0e713cf9c38 100644
--- a/gems/canvas_http/canvas_http.gemspec
+++ b/gems/canvas_http/canvas_http.gemspec
@@ -19,8 +19,8 @@ Gem::Specification.new do |spec|
   spec.add_dependency "multipart"
 
   spec.add_development_dependency "bundler", "~> 2.2"
+  spec.add_development_dependency "multipart"
   spec.add_development_dependency "rake"
   spec.add_development_dependency "rspec", "~> 3.5.0"
-  spec.add_development_dependency "multipart"
   spec.add_development_dependency "webmock", "1.24.6"
 end
diff --git a/gems/canvas_kaltura/canvas_kaltura.gemspec b/gems/canvas_kaltura/canvas_kaltura.gemspec
index b9beda63886..b0841192b13 100644
--- a/gems/canvas_kaltura/canvas_kaltura.gemspec
+++ b/gems/canvas_kaltura/canvas_kaltura.gemspec
@@ -16,11 +16,11 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_dependency "nokogiri"
   spec.add_dependency "canvas_http"
+  spec.add_dependency "canvas_slug"
   spec.add_dependency "canvas_sort"
   spec.add_dependency "multipart"
-  spec.add_dependency "canvas_slug"
+  spec.add_dependency "nokogiri"
 
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "rake"
diff --git a/gems/canvas_partman/canvas_partman.gemspec b/gems/canvas_partman/canvas_partman.gemspec
index cab7a877931..8a5d30d7da4 100644
--- a/gems/canvas_partman/canvas_partman.gemspec
+++ b/gems/canvas_partman/canvas_partman.gemspec
@@ -15,8 +15,8 @@ Gem::Specification.new do |spec|
   spec.license       = 'AGPL'
 
   spec.add_dependency 'activerecord', '>= 3.2'
-  spec.add_dependency 'pg', '>= 0.17', '< 2.0'
   spec.add_dependency 'activerecord-pg-extensions', '>= 0.3.0'
+  spec.add_dependency 'pg', '>= 0.17', '< 2.0'
 
   spec.add_development_dependency 'bundler', '~> 2.2'
   spec.add_development_dependency 'rspec', '~> 3.5.0'
diff --git a/gems/canvas_quiz_statistics/canvas_quiz_statistics.gemspec b/gems/canvas_quiz_statistics/canvas_quiz_statistics.gemspec
index 633dc1cf126..a7ce7323639 100644
--- a/gems/canvas_quiz_statistics/canvas_quiz_statistics.gemspec
+++ b/gems/canvas_quiz_statistics/canvas_quiz_statistics.gemspec
@@ -17,11 +17,11 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'html_text_helper'
 
   spec.add_development_dependency 'bundler', '~> 2.2'
-  spec.add_development_dependency 'rake'
-  spec.add_development_dependency 'rspec', "~> 3.5.0"
   spec.add_development_dependency 'byebug'
   spec.add_development_dependency 'guard'
   spec.add_development_dependency 'guard-rspec'
-  spec.add_development_dependency 'terminal-notifier-guard'
   spec.add_development_dependency 'listen', "3.0.8"
+  spec.add_development_dependency 'rake'
+  spec.add_development_dependency 'rspec', "~> 3.5.0"
+  spec.add_development_dependency 'terminal-notifier-guard'
 end
diff --git a/gems/canvas_security/canvas_security.gemspec b/gems/canvas_security/canvas_security.gemspec
index ca39d0f81eb..fe6c417fb8c 100644
--- a/gems/canvas_security/canvas_security.gemspec
+++ b/gems/canvas_security/canvas_security.gemspec
@@ -18,12 +18,12 @@ Gem::Specification.new do |spec|
 
   spec.add_dependency 'canvas_cache'
   spec.add_dependency 'canvas_errors'
-  spec.add_dependency 'rails'
-  spec.add_dependency 'json-jwt', '1.13.0'
   spec.add_dependency 'dynamic_settings'
+  spec.add_dependency 'json-jwt', '1.13.0'
+  spec.add_dependency 'rails'
 
   spec.add_development_dependency 'bundler'
-  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'byebug'
+  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'timecop'
 end
diff --git a/gems/canvas_stringex/canvas_stringex.gemspec b/gems/canvas_stringex/canvas_stringex.gemspec
index 010515bc5c3..937ec3e9eb6 100644
--- a/gems/canvas_stringex/canvas_stringex.gemspec
+++ b/gems/canvas_stringex/canvas_stringex.gemspec
@@ -21,7 +21,7 @@ Gem::Specification.new do |spec|
   spec.add_development_dependency "activerecord"
   spec.add_development_dependency "bundler", ">= 1.5", "< 3"
   spec.add_development_dependency "rake"
-  spec.add_development_dependency "sqlite3"
   spec.add_development_dependency "RedCloth"
   spec.add_development_dependency "rspec", "~> 3.5.0"
+  spec.add_development_dependency "sqlite3"
 end
diff --git a/gems/config_file/config_file.gemspec b/gems/config_file/config_file.gemspec
index 68369a29b6d..9d0bf96cca5 100644
--- a/gems/config_file/config_file.gemspec
+++ b/gems/config_file/config_file.gemspec
@@ -19,6 +19,6 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'rails', ">= 5.0"
 
   spec.add_development_dependency 'bundler'
-  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'byebug'
+  spec.add_development_dependency 'rspec'
 end
diff --git a/gems/dr_diff/dr_diff.gemspec b/gems/dr_diff/dr_diff.gemspec
index c211bbab25a..5055c59c5bd 100644
--- a/gems/dr_diff/dr_diff.gemspec
+++ b/gems/dr_diff/dr_diff.gemspec
@@ -16,8 +16,8 @@ Gem::Specification.new do |spec|
   spec.require_paths = ["lib"]
 
   spec.add_dependency "gergich", "1.2.1"
-  spec.add_development_dependency "rspec", "~> 3.5.0"
-  spec.add_development_dependency "rspec-mocks"
   spec.add_development_dependency "pry"
   spec.add_development_dependency "pry-nav"
+  spec.add_development_dependency "rspec", "~> 3.5.0"
+  spec.add_development_dependency "rspec-mocks"
 end
diff --git a/gems/dynamic_settings/dynamic_settings.gemspec b/gems/dynamic_settings/dynamic_settings.gemspec
index 07695c26f3d..06ba2e4fc81 100644
--- a/gems/dynamic_settings/dynamic_settings.gemspec
+++ b/gems/dynamic_settings/dynamic_settings.gemspec
@@ -22,6 +22,6 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'railties'
 
   spec.add_development_dependency 'bundler'
-  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'byebug'
+  spec.add_development_dependency 'rspec'
 end
diff --git a/gems/google_drive/google_drive.gemspec b/gems/google_drive/google_drive.gemspec
index f2a2d5905bb..083aab88dca 100644
--- a/gems/google_drive/google_drive.gemspec
+++ b/gems/google_drive/google_drive.gemspec
@@ -20,9 +20,9 @@ Gem::Specification.new do |spec|
   spec.add_runtime_dependency  "google-api-client", "0.8.2"
 
   spec.add_development_dependency "bundler"
+  spec.add_development_dependency "byebug"
   spec.add_development_dependency "rake"
   spec.add_development_dependency "rspec", "~> 3.5.0"
-  spec.add_development_dependency "byebug"
   spec.add_development_dependency "timecop"
   spec.add_development_dependency "webmock"
   spec.add_dependency 'faraday', '~> 0.17.3'
diff --git a/gems/html_text_helper/html_text_helper.gemspec b/gems/html_text_helper/html_text_helper.gemspec
index ace61d43a1b..aac0461a545 100644
--- a/gems/html_text_helper/html_text_helper.gemspec
+++ b/gems/html_text_helper/html_text_helper.gemspec
@@ -16,9 +16,9 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
+  spec.add_dependency 'canvas_text_helper'
   spec.add_dependency 'nokogiri'
   spec.add_dependency 'sanitize', '~> 5.2'
-  spec.add_dependency 'canvas_text_helper'
 
   spec.add_dependency 'activesupport', ">= 3.2"
 
diff --git a/gems/i18n_extraction/i18n_extraction.gemspec b/gems/i18n_extraction/i18n_extraction.gemspec
index fdeddcbb0c8..329618907d1 100644
--- a/gems/i18n_extraction/i18n_extraction.gemspec
+++ b/gems/i18n_extraction/i18n_extraction.gemspec
@@ -16,10 +16,10 @@ Gem::Specification.new do |spec|
   spec.test_files = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_dependency "sexp_processor", "~> 4.14", ">= 4.14.1"
-  spec.add_dependency "ruby_parser", "~> 3.7"
   spec.add_dependency "activesupport", ">= 3.2"
   spec.add_dependency "i18nliner", "~> 0.1"
+  spec.add_dependency "ruby_parser", "~> 3.7"
+  spec.add_dependency "sexp_processor", "~> 4.14", ">= 4.14.1"
 
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "rake"
diff --git a/gems/i18n_tasks/i18n_tasks.gemspec b/gems/i18n_tasks/i18n_tasks.gemspec
index 826fe29e596..a679095c90b 100644
--- a/gems/i18n_tasks/i18n_tasks.gemspec
+++ b/gems/i18n_tasks/i18n_tasks.gemspec
@@ -19,8 +19,8 @@ Gem::Specification.new do |spec|
   spec.add_dependency "activesupport", ">= 3.2"
 
   spec.add_dependency "i18n", ">= 0.7", "< 2"
-  spec.add_dependency "ruby_parser", "~> 3.7"
   spec.add_dependency "i18n_extraction"
+  spec.add_dependency "ruby_parser", "~> 3.7"
   spec.add_dependency "utf8_cleaner"
 
   spec.add_development_dependency "bundler", "~> 2.2"
diff --git a/gems/incoming_mail_processor/incoming_mail_processor.gemspec b/gems/incoming_mail_processor/incoming_mail_processor.gemspec
index 73429c06170..284a9d50fd8 100644
--- a/gems/incoming_mail_processor/incoming_mail_processor.gemspec
+++ b/gems/incoming_mail_processor/incoming_mail_processor.gemspec
@@ -18,12 +18,12 @@ Gem::Specification.new do |spec|
 
   spec.add_dependency "activesupport", ">= 3.2"
 
-  spec.add_dependency "mail", "~> 2.7.0"
-  spec.add_dependency "html_text_helper"
-  spec.add_dependency "utf8_cleaner"
-  spec.add_dependency "inst_statsd"
   spec.add_dependency "aws-sdk-s3"
   spec.add_dependency "aws-sdk-sqs"
+  spec.add_dependency "html_text_helper"
+  spec.add_dependency "inst_statsd"
+  spec.add_dependency "mail", "~> 2.7.0"
+  spec.add_dependency "utf8_cleaner"
 
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "byebug"
diff --git a/gems/inst_access/inst_access.gemspec b/gems/inst_access/inst_access.gemspec
index ca09839b923..6c014e838f1 100644
--- a/gems/inst_access/inst_access.gemspec
+++ b/gems/inst_access/inst_access.gemspec
@@ -20,7 +20,7 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'json-jwt', '1.13.0'
 
   spec.add_development_dependency 'bundler'
-  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'byebug'
+  spec.add_development_dependency 'rspec'
   spec.add_development_dependency 'timecop'
 end
diff --git a/gems/linked_in/linked_in.gemspec b/gems/linked_in/linked_in.gemspec
index 78840d2813d..3ad30735864 100644
--- a/gems/linked_in/linked_in.gemspec
+++ b/gems/linked_in/linked_in.gemspec
@@ -16,8 +16,8 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_dependency "oauth"
   spec.add_dependency "nokogiri"
+  spec.add_dependency "oauth"
 
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "rake"
diff --git a/gems/live_events/live_events.gemspec b/gems/live_events/live_events.gemspec
index 509dc9c4cd9..228c647906b 100644
--- a/gems/live_events/live_events.gemspec
+++ b/gems/live_events/live_events.gemspec
@@ -16,12 +16,12 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
+  spec.add_dependency "activesupport"
   spec.add_dependency "aws-sdk-kinesis"
   spec.add_dependency "inst_statsd"
-  spec.add_dependency "activesupport"
 
   spec.add_development_dependency "bundler", "~> 2.2"
-  spec.add_development_dependency "rake"
   spec.add_development_dependency "byebug"
+  spec.add_development_dependency "rake"
   spec.add_development_dependency "rspec", "~> 3.5.0"
 end
diff --git a/gems/lti-advantage/lti-advantage.gemspec b/gems/lti-advantage/lti-advantage.gemspec
index 6098ce326b8..b1612e9f0d7 100644
--- a/gems/lti-advantage/lti-advantage.gemspec
+++ b/gems/lti-advantage/lti-advantage.gemspec
@@ -28,11 +28,11 @@ Gem::Specification.new do |spec|
   spec.executables   = spec.files.grep(%r{^exe/}) { |f| File.basename(f) }
   spec.require_paths = ["lib"]
 
-  spec.add_runtime_dependency 'json-jwt', '~> 1.5'
   spec.add_runtime_dependency "activemodel", ">= 5.1"
+  spec.add_runtime_dependency 'json-jwt', '~> 1.5'
 
-  spec.add_development_dependency "redcarpet"
   spec.add_development_dependency "bundler", "~> 2.2"
   spec.add_development_dependency "rake", "~> 10.0"
+  spec.add_development_dependency "redcarpet"
   spec.add_development_dependency "rspec", "~> 3.0"
 end
diff --git a/gems/multipart/multipart.gemspec b/gems/multipart/multipart.gemspec
index 29a692567a1..9ba428c4e4a 100644
--- a/gems/multipart/multipart.gemspec
+++ b/gems/multipart/multipart.gemspec
@@ -16,12 +16,12 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_dependency "mime-types", "~> 3.2"
   spec.add_dependency "canvas_slug"
+  spec.add_dependency "mime-types", "~> 3.2"
 
   spec.add_development_dependency "bundler", "~> 2.2"
-  spec.add_development_dependency "rake"
-  spec.add_development_dependency "rspec", "~> 3.5.0"
   spec.add_development_dependency "rack", "~> 1.6"
   spec.add_development_dependency "rack-test", "0.6.2"
+  spec.add_development_dependency "rake"
+  spec.add_development_dependency "rspec", "~> 3.5.0"
 end
diff --git a/gems/plugins/academic_benchmark/academic_benchmark.gemspec b/gems/plugins/academic_benchmark/academic_benchmark.gemspec
index 6bd9961eb30..98e967f57f6 100644
--- a/gems/plugins/academic_benchmark/academic_benchmark.gemspec
+++ b/gems/plugins/academic_benchmark/academic_benchmark.gemspec
@@ -15,6 +15,6 @@ Gem::Specification.new do |spec|
   spec.files = Dir["{app,config,db,lib}/**/*"]
   spec.test_files = Dir["spec_canvas/**/*"]
 
-  spec.add_dependency "rails", ">= 3.2"
   spec.add_dependency "academic_benchmarks", "~> 1.1.0"
+  spec.add_dependency "rails", ">= 3.2"
 end
diff --git a/gems/plugins/moodle_importer/moodle_importer.gemspec b/gems/plugins/moodle_importer/moodle_importer.gemspec
index 676e0eae1eb..61af3b36b66 100644
--- a/gems/plugins/moodle_importer/moodle_importer.gemspec
+++ b/gems/plugins/moodle_importer/moodle_importer.gemspec
@@ -18,6 +18,6 @@ Gem::Specification.new do |s|
   s.files = Dir["{lib}/**/*"]
   s.test_files = Dir["spec_canvas/**/*"]
 
-  s.add_dependency "rails", ">= 3.2"
   s.add_dependency "moodle2cc", "0.2.41"
+  s.add_dependency "rails", ">= 3.2"
 end
diff --git a/gems/request_context/request_context.gemspec b/gems/request_context/request_context.gemspec
index 8366f40f7e8..599acb05856 100644
--- a/gems/request_context/request_context.gemspec
+++ b/gems/request_context/request_context.gemspec
@@ -16,8 +16,8 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^(test|spec|features)/})
   spec.require_paths = ["lib"]
 
-  spec.add_dependency 'canvas_security'
   spec.add_dependency 'actionpack'
+  spec.add_dependency 'canvas_security'
   spec.add_dependency 'railties'
 
   spec.add_development_dependency 'bundler'
diff --git a/gems/rubocop-canvas/rubocop-canvas.gemspec b/gems/rubocop-canvas/rubocop-canvas.gemspec
index 1c1e13b7809..8f8b206c89d 100644
--- a/gems/rubocop-canvas/rubocop-canvas.gemspec
+++ b/gems/rubocop-canvas/rubocop-canvas.gemspec
@@ -22,9 +22,9 @@ Gem::Specification.new do |spec|
   spec.add_dependency "rubocop", "~> 1.19"
 
   spec.add_development_dependency "bundler", "~> 2.2"
+  spec.add_development_dependency "byebug"
   spec.add_development_dependency "pry", "~> 0.10.1"
   spec.add_development_dependency "pry-nav", "~> 0.2.4"
   spec.add_development_dependency "rake", "~> 10.0"
   spec.add_development_dependency "rspec", "~> 3.5.0"
-  spec.add_development_dependency "byebug"
 end
diff --git a/gems/tatl_tael/tatl_tael.gemspec b/gems/tatl_tael/tatl_tael.gemspec
index 7327503ec2a..f4b0042ad12 100644
--- a/gems/tatl_tael/tatl_tael.gemspec
+++ b/gems/tatl_tael/tatl_tael.gemspec
@@ -15,7 +15,7 @@ Gem::Specification.new do |spec|
   spec.test_files    = spec.files.grep(%r{^spec/})
   spec.require_paths = ["lib"]
 
-  spec.add_development_dependency "rspec", "~> 3.5.0"
   spec.add_development_dependency "fakefs", "~> 1.2"
+  spec.add_development_dependency "rspec", "~> 3.5.0"
   spec.add_development_dependency "timecop", "0.8.1"
 end
diff --git a/gems/turnitin_api/turnitin_api.gemspec b/gems/turnitin_api/turnitin_api.gemspec
index 47ea1181be5..615a4f27dec 100644
--- a/gems/turnitin_api/turnitin_api.gemspec
+++ b/gems/turnitin_api/turnitin_api.gemspec
@@ -18,10 +18,10 @@ Gem::Specification.new do |spec|
   spec.executables   = spec.files.grep(%r{^exe/}) { |f| File.basename(f) }
   spec.require_paths = ["lib"]
 
-  spec.add_dependency 'simple_oauth', '0.2'
-  spec.add_dependency 'webmock', '3.3.0'
   spec.add_dependency 'faraday', '~> 0.17.3'
   spec.add_dependency 'faraday_middleware', '~> 0.8'
+  spec.add_dependency 'simple_oauth', '0.2'
+  spec.add_dependency 'webmock', '3.3.0'
 
   spec.add_development_dependency "bundler",  "~> 2.2"
   spec.add_development_dependency "rake", "~> 10.0"
diff --git a/gems/twitter/twitter.gemspec b/gems/twitter/twitter.gemspec
index 1cfc201ade3..2392f640326 100644
--- a/gems/twitter/twitter.gemspec
+++ b/gems/twitter/twitter.gemspec
@@ -20,7 +20,7 @@ Gem::Specification.new do |spec|
   spec.add_dependency "oauth"
 
   spec.add_development_dependency "bundler", "~> 2.2"
+  spec.add_development_dependency "byebug"
   spec.add_development_dependency "rake"
   spec.add_development_dependency "rspec", "~> 3.5.0"
-  spec.add_development_dependency "byebug"
 end