diff --git a/CalSmokeApp/Gemfile b/CalSmokeApp/Gemfile
index e38e626..e48cde0 100644
--- a/CalSmokeApp/Gemfile
+++ b/CalSmokeApp/Gemfile
@@ -3,19 +3,19 @@ source 'https://rubygems.org'
 gem 'calabash-cucumber', :github => "calabash/calabash-ios", :branch => "develop"
 gem "cucumber", "2.99.0"
 gem "run_loop", :github => "calabash/run_loop", :branch => "develop"
-gem "json", "1.8.6"
+gem "json", "2.5.1"
 
 # workflow and build tools
 gem 'retriable', '~> 2.0'
-gem 'rake', '~> 10.3'
-gem 'bundler', '2.0.2'
+gem 'rake', '~> 13.0.3'
+gem 'bundler', '2.2.7'
 gem 'xcpretty', '~> 0.1'
 gem "xamarin-test-cloud", "~> 2.0"
 gem 'rspec', '~> 3.0'
 gem 'chronic', '>= 0.10', '< 1.0'
 gem 'pry'
 gem 'pry-nav'
-gem 'luffa', '~> 1.0', '>= 1.0.2'
+gem 'luffa'
 gem 'guard-rspec', '~> 4.3'
 gem 'guard-bundler', '~> 2.0'
 gem 'growl', '~> 1.0'
diff --git a/CalSmokeApp/bin/make/ipa-cal.sh b/CalSmokeApp/bin/make/ipa-cal.sh
index 553659a..87d2e87 100755
--- a/CalSmokeApp/bin/make/ipa-cal.sh
+++ b/CalSmokeApp/bin/make/ipa-cal.sh
@@ -134,16 +134,16 @@ cat >"${XTC_DIR}/Gemfile" <<EOF
 source "https://rubygems.org"
 
 gem "calabash-cucumber"
-gem "json", "1.8.6"
+gem "json", "2.5.1"
 gem "cucumber", "~> 2.0"
 gem 'retriable', '~> 2.0'
 gem "xamarin-test-cloud", "~> 2.0"
-gem 'rake', '~> 10.3'
+gem 'rake', '~> 13.0.3'
 gem 'xcpretty', '~> 0.1'
 gem 'rspec', '~> 3.0'
 gem 'pry'
 gem 'pry-nav'
-gem 'luffa', '~> 1.0', '>= 1.0.2'
+gem 'luffa'
 gem 'chronic', '>= 0.10.2', '< 1.0'
 EOF
 
diff --git a/Gemfile b/Gemfile
index cd9e799..c955349 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,6 +1,6 @@
 source "https://rubygems.org"
 
 gem "run_loop", github: "calabash/run_loop", branch: "develop"
-gem "json", "1.8.6"
+gem "json", "2.5.1"
 gem "luffa", github: "calabash/luffa", branch: "develop"
-gem "bundler", "2.0.2"
+gem "bundler", "2.2.7"
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 5444480..d8577ca 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -61,8 +61,8 @@ jobs:
 
   - script: |
       gem uninstall bundler
-      gem install bundler -v 2.0.2
-    displayName: "Install bundler 2.0.2"
+      gem install bundler -v 2.2.7
+    displayName: "Install bundler 2.2.7"
 
   - script: |
       set -e