diff --git a/.github/workflows/ruby.yml b/.github/workflows/ruby.yml
index 7594206b0..2dbb133ec 100644
--- a/.github/workflows/ruby.yml
+++ b/.github/workflows/ruby.yml
@@ -24,7 +24,7 @@ jobs:
     - name: Set up Ruby
       uses: ruby/setup-ruby@v1
       with:
-        ruby-version: 2.4.2
+        ruby-version: 2.5.9
         bundler-cache: true
       env:
         BUNDLE_JOBS: 4
diff --git a/.ruby-version b/.ruby-version
index 8e8299dcc..30f69e8cc 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-2.4.2
+2.5.9
diff --git a/Dockerfile b/Dockerfile
index 7f2840960..81502480b 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,4 +1,4 @@
-FROM ruby:2.4.2
+FROM ruby:2.5.9
 
 # Default node version on apt is old. This makes sure a recent version is installed
 # This step also runs apt-get update
diff --git a/Gemfile b/Gemfile
index 4f5aa87ee..aa6bd382c 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,5 +1,5 @@
 source 'https://rubygems.org'
-ruby '2.4.2'
+ruby '2.5.9'
 
 gem 'rails', '4.2.11.3'
 
diff --git a/Gemfile.lock b/Gemfile.lock
index b3b0b9fb8..aa8a03b2b 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -464,7 +464,7 @@ DEPENDENCIES
   will_paginate
 
 RUBY VERSION
-   ruby 2.4.2p198
+   ruby 2.5.9p229
 
 BUNDLED WITH
    1.17.3
diff --git a/native-installation-instructions.md b/native-installation-instructions.md
index f4decafa2..3e1bf268c 100644
--- a/native-installation-instructions.md
+++ b/native-installation-instructions.md
@@ -16,19 +16,20 @@ These are the original instructions for natively installing the app to your mach
 
 ## Set up a Ruby Environment
 
-You will need to install Ruby 2.4.2 using RVM or rbenv.
+You will need to install Ruby 2.7.2 using RVM or rbenv.
 
 ### Option 1: Using [rvm](https://rvm.io/rvm/install)
 
 ```bash
-rvm install 2.4.2
+CPPFLAGS=-DUSE_FFI_CLOSURE_ALLOC rvm install 2.5.9
 ```
+We need to set the CPPFLAGS env variable to be able to install Ruby 2.5.9 on M1 Mac machines. See more: [https://github.com/ffi/ffi/issues/869#issuecomment-1233000037](https://github.com/ffi/ffi/issues/869#issuecomment-1233000037)
 
 ### Option 2: Using [rbenv](https://github.com/sstephenson/rbenv) and [ruby-build](https://github.com/sstephenson/ruby-build)
 
 ```bash
-rbenv install 2.4.2
-rbenv global 2.4.2
+rbenv install 2.5.9
+rbenv global 2.5.9
 ```
 
 ## Install and run PostgreSQL