diff --git a/Gemfile b/Gemfile
index 76b527470..3b75ccf51 100644
--- a/Gemfile
+++ b/Gemfile
@@ -163,7 +163,7 @@ end
 # Windows and Mac do not include zoneinfo files, so bundle the tzinfo-data gem
 gem 'tzinfo-data'
 
-gem 'highline', '~> 2.0'
+gem 'highline', '~> 3.1'
 # Ruby wrapper around slack API
 gem 'slack-ruby-client', '~> 3.2'
 # Slack notification formatting
diff --git a/Gemfile.lock b/Gemfile.lock
index ddd8d07c6..45179128f 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -318,7 +318,8 @@ GEM
       logger
     health_check (3.1.0)
       railties (>= 5.0)
-    highline (2.1.0)
+    highline (3.1.2)
+      reline
     htmlentities (4.4.2)
     http-accept (1.7.0)
     http-cookie (1.1.6)
@@ -820,7 +821,7 @@ DEPENDENCIES
   haml-rails (~> 3.1)
   has_scope (~> 0.9.0)
   health_check (~> 3.1)
-  highline (~> 2.0)
+  highline (~> 3.1)
   inspec-core (~> 7.1)!
   jbuilder (~> 2.7)
   jsbundling-rails