diff --git a/.buildkite/shared-pipeline-vars b/.buildkite/shared-pipeline-vars
index d455cab46..a7420686c 100644
--- a/.buildkite/shared-pipeline-vars
+++ b/.buildkite/shared-pipeline-vars
@@ -1,8 +1,9 @@
 #!/bin/bash
 
-export IMAGE_ID="xcode-26.1.1"
+export IMAGE_ID="xcode-27.0-beta"
 export CI_TOOLKIT="automattic/a8c-ci-toolkit#5.7.0"
 export DOCKER_PLUGIN="docker#v5.13.0"
 SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
-export RUBY_VERSION="$(cat "$SCRIPT_DIR/../.ruby-version")"
+RUBY_VERSION="$(cat "$SCRIPT_DIR/../.ruby-version")"
+export RUBY_VERSION
 export DOCKER_RUBY_IMAGE="public.ecr.aws/docker/library/ruby:$RUBY_VERSION"
diff --git a/.ruby-version b/.ruby-version
index 19ef286ee..7bcbb3808 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1,2 +1 @@
-3.2.2
-
+3.4.9
diff --git a/Gemfile b/Gemfile
index b38013f18..2c7c50996 100644
--- a/Gemfile
+++ b/Gemfile
@@ -4,12 +4,21 @@ source('https://rubygems.org')
 
 gemspec
 
+# Only needed for specs (Time.use_zone, String#to_time, Hash#slice!)
+gem 'activesupport', '~> 8.1'
 gem 'buildkite-test_collector', '~> 2.3'
 gem 'codecov', require: false
 gem 'danger-dangermattic', '~> 1.0'
-gem 'webmock', require: false
-gem 'yard'
-
 # Security: https://github.com/lostisland/faraday/pull/1665
 # Faraday 2.0 is not compatible with Fastlane
+# See also https://github.com/fastlane/fastlane/issues/21334
 gem 'faraday', '~> 1.10', '>= 1.10.5'
+gem 'pry', '~> 0.12.2'
+gem 'rmagick', '~> 5.3'
+gem 'rspec', '~> 3.8'
+gem 'rspec_junit_formatter', '~> 0.4.1'
+gem 'rubocop', '~> 1.65'
+gem 'rubocop-rspec', '3.0'
+gem 'simplecov', '~> 0.16.1'
+gem 'webmock', require: false
+gem 'yard'
diff --git a/Gemfile.lock b/Gemfile.lock
index 009325290..da239d1fb 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -6,7 +6,7 @@ PATH
       chroma (= 0.2.0)
       diffy (~> 3.3)
       dotenv (~> 2.8)
-      fastlane (~> 2.235)
+      fastlane (~> 2.236)
       gettext (~> 3.5)
       git (~> 1.3)
       google-cloud-storage (~> 1.31)
@@ -158,7 +158,7 @@ GEM
     faraday_middleware (1.2.1)
       faraday (~> 1.0)
     fastimage (2.4.1)
-    fastlane (2.235.0)
+    fastlane (2.236.1)
       CFPropertyList (>= 2.3, < 5.0.0)
       abbrev (~> 0.1)
       addressable (>= 2.8, < 3.0.0)
@@ -187,9 +187,10 @@ GEM
       highline (~> 2.0)
       http-cookie (~> 1.0.5)
       json (< 3.0.0)
-      jwt (>= 2.1.0, < 4)
+      jwt (>= 2.10.3, < 4)
       logger (>= 1.6, < 2.0)
       mini_magick (>= 4.9.4, < 5.0.0)
+      multi_json (~> 1.12)
       multipart-post (>= 2.0.0, < 3.0.0)
       mutex_m (~> 0.3)
       naturally (~> 2.2)
@@ -436,11 +437,9 @@ PLATFORMS
 DEPENDENCIES
   activesupport (~> 8.1)
   buildkite-test_collector (~> 2.3)
-  bundler (~> 2.0)
   codecov
   danger-dangermattic (~> 1.0)
   faraday (~> 1.10, >= 1.10.5)
-  fastlane (~> 2.210)
   fastlane-plugin-wpmreleasetoolkit!
   pry (~> 0.12.2)
   rmagick (~> 5.3)
@@ -453,4 +452,4 @@ DEPENDENCIES
   yard
 
 BUNDLED WITH
-   2.6.8
+  4.0.14
diff --git a/fastlane-plugin-wpmreleasetoolkit.gemspec b/fastlane-plugin-wpmreleasetoolkit.gemspec
index a0adb7a6a..10be1bd9f 100644
--- a/fastlane-plugin-wpmreleasetoolkit.gemspec
+++ b/fastlane-plugin-wpmreleasetoolkit.gemspec
@@ -30,7 +30,7 @@ Gem::Specification.new do |spec|
   spec.add_dependency 'chroma', '0.2.0'
   spec.add_dependency 'diffy', '~> 3.3'
   spec.add_dependency 'dotenv', '~> 2.8'
-  spec.add_dependency 'fastlane', '~> 2.235'
+  spec.add_dependency 'fastlane', '~> 2.236'
   spec.add_dependency 'gettext', '~> 3.5'
   spec.add_dependency 'git', '~> 1.3'
   spec.add_dependency 'java-properties', '~> 0.3.0'
@@ -45,18 +45,4 @@ Gem::Specification.new do |spec|
 
   # `google-cloud-storage` is required by fastlane, but we pin it in case it's not in the future
   spec.add_dependency 'google-cloud-storage', '~> 1.31'
-
-  # Only needed for specs (Time.use_zone, String#to_time, Hash#slice!)
-  spec.add_development_dependency 'activesupport', '~> 8.1'
-  spec.add_development_dependency 'bundler', '~> 2.0'
-  # Use at least Fastlane 2.210.0 to ensure compatibility with the Xcode 14 toolchain
-  # See https://github.com/fastlane/fastlane/releases/tag/2.210.0
-  spec.add_development_dependency 'fastlane', '~> 2.210'
-  spec.add_development_dependency 'pry', '~> 0.12.2'
-  spec.add_development_dependency 'rmagick', '~> 5.3'
-  spec.add_development_dependency 'rspec', '~> 3.8'
-  spec.add_development_dependency 'rspec_junit_formatter', '~> 0.4.1'
-  spec.add_development_dependency 'rubocop', '~> 1.65'
-  spec.add_development_dependency 'rubocop-rspec', '3.0'
-  spec.add_development_dependency 'simplecov', '~> 0.16.1'
 end