diff --git a/Gemfile b/Gemfile
index 8be63cff96..4076add5b9 100644
--- a/Gemfile
+++ b/Gemfile
@@ -146,10 +146,11 @@ group :test do
 end
 
 group :development do
-  gem 'byebug', '~> 9.0.0' # 9.1 requires ruby 2.2
+  gem 'byebug', '~> 11.0' # 11.1 requires ruby 2.4
   gem 'debugger-linecache'
   gem "newrelic_rpm", "~> 3.0"
-  gem 'pry-byebug', '>= 3.4.3'
+  gem "pry", "~> 0.12.0" # pry 0.13 is not compatible with pry-byebug 3.7
+  gem 'pry-byebug', '~> 3.7' # 3.8 requires ruby 2.4
   gem 'rubocop'
   gem 'rubocop-rails'
   gem 'spring', '1.7.2'
diff --git a/Gemfile.lock b/Gemfile.lock
index 3a9e5fb1da..a77cb44b26 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -150,7 +150,7 @@ GEM
     bugsnag (6.13.1)
       concurrent-ruby (~> 1.0)
     builder (3.0.4)
-    byebug (9.0.6)
+    byebug (11.0.1)
     cancan (1.6.10)
     capybara (2.18.0)
       addressable
@@ -498,8 +498,8 @@ GEM
     pry (0.12.2)
       coderay (~> 1.1.0)
       method_source (~> 0.9.0)
-    pry-byebug (3.4.3)
-      byebug (>= 9.0, < 9.1)
+    pry-byebug (3.7.0)
+      byebug (~> 11.0)
       pry (~> 0.10)
     public_suffix (4.0.3)
     rack (1.4.7)
@@ -700,7 +700,7 @@ DEPENDENCIES
   aws-sdk
   blockenspiel
   bugsnag
-  byebug (~> 9.0.0)
+  byebug (~> 11.0)
   capybara (>= 2.18.0)
   catalog!
   coffee-rails (~> 3.2.1)
@@ -750,7 +750,8 @@ DEPENDENCIES
   paper_trail (~> 5.2.3)
   paperclip (~> 3.4.1)
   pg (~> 0.21.0)
-  pry-byebug (>= 3.4.3)
+  pry (~> 0.12.0)
+  pry-byebug (~> 3.7)
   rack-mini-profiler (< 3.0.0)
   rack-rewrite
   rack-ssl
@@ -796,4 +797,4 @@ RUBY VERSION
    ruby 2.3.7p456
 
 BUNDLED WITH
-   1.17.2
+   1.17.3