diff --git a/Dockerfile.dev b/Dockerfile.dev
index 8b7e062d..8a2e0ceb 100644
--- a/Dockerfile.dev
+++ b/Dockerfile.dev
@@ -6,6 +6,9 @@ RUN apk update --no-cache && \
     apk add build-base postgresql-dev git nodejs yarn tzdata bash sqlite-dev npm && \
     mkdir -p /app
 
+# https://github.com/pry/pry/issues/1248
+RUN apk --update add less
+
 WORKDIR /app
 
 COPY ./lib/ /app/lib/
diff --git a/Dockerfile.test b/Dockerfile.test
index ac7beb30..1d2d6fd4 100644
--- a/Dockerfile.test
+++ b/Dockerfile.test
@@ -6,6 +6,9 @@ RUN apk update --no-cache && \
     apk add build-base postgresql-dev git nodejs yarn tzdata bash sqlite-dev npm && \
     mkdir -p /app
 
+# https://github.com/pry/pry/issues/1248
+RUN apk --update add less
+
 WORKDIR /app
 
 COPY ./lib/ /app/lib/
diff --git a/Gemfile b/Gemfile
index a7d3b66d..90a2c109 100644
--- a/Gemfile
+++ b/Gemfile
@@ -23,11 +23,11 @@ group :development, :test do
   gem 'simplecov', require: false, group: :test
   gem 'byebug'
   gem 'webmock'
+  gem 'pry-rails'
+  gem 'pry-byebug'
 end
 
 group :test do
-  gem 'pry-rails'
-  gem 'pry-byebug'
   gem "generator_spec"
   # gem "rspec-retry" # repeating flaky tests
   # gem "rspec-wait", "~> 0.0.9"
diff --git a/spec/dummy/config/initializers/backtrace_silencers.rb b/spec/dummy/config/initializers/backtrace_silencers.rb
index 59385cdf..8fa57b9d 100644
--- a/spec/dummy/config/initializers/backtrace_silencers.rb
+++ b/spec/dummy/config/initializers/backtrace_silencers.rb
@@ -1,7 +1,13 @@
 # Be sure to restart your server when you modify this file.
 
-# You can add backtrace silencers for libraries that you're using but don't wish to see in your backtraces.
-# Rails.backtrace_cleaner.add_silencer { |line| line =~ /my_noisy_library/ }
+# https://api.rubyonrails.org/classes/ActiveSupport/BacktraceCleaner.html
+# https://github.com/rails/rails/blob/main/activesupport/lib/active_support/backtrace_cleaner.rb
 
-# You can also remove all the silencers if you're trying to debug a problem that might stem from framework code.
-# Rails.backtrace_cleaner.remove_silencers!
+# Show only stacktrace of matestack or the dummy app and not the other gems
+Rails.backtrace_cleaner.remove_silencers!
+Rails.backtrace_cleaner.add_silencer { |line| line.include? "/usr/local/bundle/gems" }
+
+# Remove docker-path prefix "/app/" from paths to allow advanced terminal features
+# like iTerm's "semantic history" which would be broken by the docker path.
+Rails.backtrace_cleaner.remove_filters!
+Rails.backtrace_cleaner.add_filter { |line| line.gsub(/^\/app\//, '') }