diff --git a/.buildkite/pipeline.yml b/.buildkite/pipeline.yml
index bc33a6bc9..b55a82e0d 100644
--- a/.buildkite/pipeline.yml
+++ b/.buildkite/pipeline.yml
@@ -1,10 +1,10 @@
 # Nodes with values to reuse in the pipeline.
 common_params:
   plugins: &common_plugins
-  - &bash_cache automattic/bash-cache#2.0.0: ~
+  - &bash_cache automattic/bash-cache#2.8.0
   # Common environment values to use with the `env` key.
   env: &common_env
-    IMAGE_ID: xcode-13
+    IMAGE_ID: xcode-14
 
 # This is the default pipeline – it will build and test the app
 steps:
@@ -14,9 +14,6 @@ steps:
   - label: "🧪 Build and Test"
     key: "test"
     command: |
-      # See https://github.com/Automattic/bash-cache-buildkite-plugin/issues/16
-      gem install bundler:2.3.4
-
       build_and_test_pod
     env: *common_env
     plugins: *common_plugins
@@ -27,9 +24,6 @@ steps:
   - label: "🔬 Validate Podspecs"
     key: "validate"
     command: |
-      # See https://github.com/Automattic/bash-cache-buildkite-plugin/issues/16
-      gem install bundler:2.3.4
-
       validate_podspec
     env: *common_env
     plugins: *common_plugins
@@ -40,9 +34,6 @@ steps:
   - label: "🧹 Lint"
     key: "lint"
     command: |
-      # See https://github.com/Automattic/bash-cache-buildkite-plugin/issues/16
-      gem install bundler:2.3.4
-
       lint_pod
     env: *common_env
     plugins: *common_plugins
diff --git a/.buildkite/publish-aztec-pod.sh b/.buildkite/publish-aztec-pod.sh
index 2343776da..a0beab3ba 100644
--- a/.buildkite/publish-aztec-pod.sh
+++ b/.buildkite/publish-aztec-pod.sh
@@ -5,9 +5,6 @@ SPECS_REPO="git@github.com:wordpress-mobile/cocoapods-specs.git"
 SLACK_WEBHOOK=$PODS_SLACK_WEBHOOK
 
 echo "--- :rubygems: Setting up Gems"
-# See https://github.com/Automattic/bash-cache-buildkite-plugin/issues/16
-gem install bundler:2.3.4
-
 install_gems
 
 echo "--- :cocoapods: Publishing Pod to CocoaPods CDN"
diff --git a/.buildkite/publish-editor.pod.sh b/.buildkite/publish-editor.pod.sh
index f6534c70f..68dbb507c 100644
--- a/.buildkite/publish-editor.pod.sh
+++ b/.buildkite/publish-editor.pod.sh
@@ -5,9 +5,6 @@ SPECS_REPO="git@github.com:wordpress-mobile/cocoapods-specs.git"
 SLACK_WEBHOOK=$PODS_SLACK_WEBHOOK
 
 echo "--- :rubygems: Setting up Gems"
-# See https://github.com/Automattic/bash-cache-buildkite-plugin/issues/16
-gem install bundler:2.3.4
-
 install_gems
 
 echo "--- :cocoapods: Publishing Pod to CocoaPods CDN"
diff --git a/.ruby-version b/.ruby-version
index 2714f5313..a4dd9dba4 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.6.4
+2.7.4
diff --git a/Gemfile b/Gemfile
index 298568a74..a767c6f1a 100644
--- a/Gemfile
+++ b/Gemfile
@@ -2,6 +2,6 @@
 
 source 'https://rubygems.org'
 
-gem 'cocoapods', '~> 1.8.0'
+gem 'cocoapods', '~> 1.11'
 gem 'fastlane', '~> 2.189'
 gem 'rubocop', '~> 1.18'
diff --git a/Gemfile.lock b/Gemfile.lock
index bd7465897..4c120b353 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -3,11 +3,12 @@ GEM
   specs:
     CFPropertyList (3.0.5)
       rexml
-    activesupport (4.2.11.3)
-      i18n (~> 0.7)
-      minitest (~> 5.1)
-      thread_safe (~> 0.3, >= 0.3.4)
-      tzinfo (~> 1.1)
+    activesupport (6.1.7)
+      concurrent-ruby (~> 1.0, >= 1.0.2)
+      i18n (>= 1.6, < 2)
+      minitest (>= 5.1)
+      tzinfo (~> 2.0)
+      zeitwerk (~> 2.3)
     addressable (2.8.0)
       public_suffix (>= 2.0.2, < 5.0)
     algoliasearch (1.27.5)
@@ -34,37 +35,39 @@ GEM
       aws-eventstream (~> 1, >= 1.0.2)
     babosa (1.0.4)
     claide (1.1.0)
-    cocoapods (1.8.4)
-      activesupport (>= 4.0.2, < 5)
+    cocoapods (1.11.3)
+      addressable (~> 2.8)
       claide (>= 1.0.2, < 2.0)
-      cocoapods-core (= 1.8.4)
+      cocoapods-core (= 1.11.3)
       cocoapods-deintegrate (>= 1.0.3, < 2.0)
-      cocoapods-downloader (>= 1.2.2, < 2.0)
+      cocoapods-downloader (>= 1.4.0, < 2.0)
       cocoapods-plugins (>= 1.0.0, < 2.0)
       cocoapods-search (>= 1.0.0, < 2.0)
-      cocoapods-stats (>= 1.0.0, < 2.0)
       cocoapods-trunk (>= 1.4.0, < 2.0)
       cocoapods-try (>= 1.1.0, < 2.0)
       colored2 (~> 3.1)
       escape (~> 0.0.4)
       fourflusher (>= 2.3.0, < 3.0)
       gh_inspector (~> 1.0)
-      molinillo (~> 0.6.6)
+      molinillo (~> 0.8.0)
       nap (~> 1.0)
-      ruby-macho (~> 1.4)
-      xcodeproj (>= 1.11.1, < 2.0)
-    cocoapods-core (1.8.4)
-      activesupport (>= 4.0.2, < 6)
+      ruby-macho (>= 1.0, < 3.0)
+      xcodeproj (>= 1.21.0, < 2.0)
+    cocoapods-core (1.11.3)
+      activesupport (>= 5.0, < 7)
+      addressable (~> 2.8)
       algoliasearch (~> 1.0)
       concurrent-ruby (~> 1.1)
       fuzzy_match (~> 2.0.4)
       nap (~> 1.0)
+      netrc (~> 0.11)
+      public_suffix (~> 4.0)
+      typhoeus (~> 1.0)
     cocoapods-deintegrate (1.0.5)
-    cocoapods-downloader (1.5.1)
+    cocoapods-downloader (1.6.3)
     cocoapods-plugins (1.0.0)
       nap
     cocoapods-search (1.0.1)
-    cocoapods-stats (1.1.0)
     cocoapods-trunk (1.6.0)
       nap (>= 0.8, < 2.0)
       netrc (~> 0.11)
@@ -73,7 +76,7 @@ GEM
     colored2 (3.1.2)
     commander (4.6.0)
       highline (~> 2.0.0)
-    concurrent-ruby (1.1.9)
+    concurrent-ruby (1.1.10)
     declarative (0.0.20)
     digest-crc (0.6.4)
       rake (>= 12.0.0, < 14.0.0)
@@ -82,6 +85,8 @@ GEM
     dotenv (2.7.6)
     emoji_regex (3.2.3)
     escape (0.0.4)
+    ethon (0.15.0)
+      ffi (>= 1.15.0)
     excon (0.91.0)
     faraday (1.9.3)
       faraday-em_http (~> 1.0)
@@ -151,6 +156,7 @@ GEM
       xcodeproj (>= 1.13.0, < 2.0.0)
       xcpretty (~> 0.3.0)
       xcpretty-travis-formatter (>= 0.0.3)
+    ffi (1.15.5)
     fourflusher (2.3.1)
     fuzzy_match (2.0.4)
     gh_inspector (1.1.3)
@@ -196,16 +202,16 @@ GEM
     http-cookie (1.0.4)
       domain_name (~> 0.5)
     httpclient (2.8.3)
-    i18n (0.9.5)
+    i18n (1.12.0)
       concurrent-ruby (~> 1.0)
     jmespath (1.5.0)
-    json (2.6.1)
+    json (2.6.2)
     jwt (2.3.0)
     memoist (0.16.2)
     mini_magick (4.11.0)
     mini_mime (1.1.2)
-    minitest (5.15.0)
-    molinillo (0.6.6)
+    minitest (5.16.3)
+    molinillo (0.8.0)
     multi_json (1.15.0)
     multipart-post (2.0.0)
     nanaimo (0.3.0)
@@ -240,7 +246,7 @@ GEM
       unicode-display_width (>= 1.4.0, < 3.0)
     rubocop-ast (1.15.1)
       parser (>= 3.0.1.1)
-    ruby-macho (1.4.0)
+    ruby-macho (2.5.1)
     ruby-progressbar (1.11.0)
     ruby2_keywords (0.0.5)
     rubyzip (2.3.2)
@@ -255,14 +261,15 @@ GEM
       naturally
     terminal-notifier (2.0.0)
     terminal-table (1.6.0)
-    thread_safe (0.3.6)
     trailblazer-option (0.1.2)
     tty-cursor (0.7.1)
     tty-screen (0.8.1)
     tty-spinner (0.9.3)
       tty-cursor (~> 0.7)
-    tzinfo (1.2.9)
-      thread_safe (~> 0.1)
+    typhoeus (1.4.0)
+      ethon (>= 0.9.0)
+    tzinfo (2.0.5)
+      concurrent-ruby (~> 1.0)
     uber (0.1.0)
     unf (0.1.4)
       unf_ext
@@ -270,7 +277,7 @@ GEM
     unicode-display_width (2.1.0)
     webrick (1.7.0)
     word_wrap (1.0.0)
-    xcodeproj (1.21.0)
+    xcodeproj (1.22.0)
       CFPropertyList (>= 2.3.3, < 4.0)
       atomos (~> 0.1.3)
       claide (>= 1.0.2, < 2.0)
@@ -281,14 +288,15 @@ GEM
       rouge (~> 2.0.7)
     xcpretty-travis-formatter (1.0.1)
       xcpretty (~> 0.2, >= 0.0.7)
+    zeitwerk (2.6.1)
 
 PLATFORMS
   ruby
 
 DEPENDENCIES
-  cocoapods (~> 1.8.0)
+  cocoapods (~> 1.11)
   fastlane (~> 2.189)
   rubocop (~> 1.18)
 
 BUNDLED WITH
-   2.2.33
+   2.3.22
diff --git a/fastlane/Fastfile b/fastlane/Fastfile
index 252f581a6..7af8e3ade 100644
--- a/fastlane/Fastfile
+++ b/fastlane/Fastfile
@@ -2,8 +2,8 @@
 
 default_platform(:ios)
 
-TEST_RUNTIME = 'iOS 15.0'
-TEST_DEVICE = 'iPhone 11'
+TEST_RUNTIME = 'iOS 16.0'
+TEST_DEVICE = 'iPhone 14'
 
 platform :ios do
   desc 'Builds the project and runs tests'