diff --git a/Gemfile b/Gemfile
index bfba58b670..76c1c1f3f9 100644
--- a/Gemfile
+++ b/Gemfile
@@ -5,110 +5,106 @@ source "https://rubygems.org"
 ruby "3.3.8"
 gem "rails", "~> 7.2"
 
-gem "after_party" # post-deployment tasks
-gem "amazing_print" # easier console reading
+gem "after_party" # Post-deployment tasks
+gem "amazing_print" # Easier console reading
 gem "authtrail" # Track Devise login activity
 gem "azure-storage-blob", require: false
-gem "blueprinter" # for JSON serialization
-gem "bugsnag" # tracking errors in prod
-gem "caxlsx", "~> 4.2" # excel spreadsheets - TODO can we remove this version restriction?
-gem "caxlsx_rails", "~> 0.6.4" # excel spreadsheets - TODO can we remove this version restriction?
-gem "cssbundling-rails", "~> 1.4" # compiles css
-gem "delayed_job_active_record"
-gem "devise" # for authentication
-gem "devise_invitable"
-gem "draper" # adds decorators for cleaner presentation logic
-gem "faker" # creates realistic seed data, valuable for staging and demos
-gem "filterrific" # filtering and sorting of models
-gem "friendly_id", "~> 5.5.1" # allows us to use a slug instead of casa case ids in their URLs
-gem "groupdate" # Group Data
-gem "httparty" # for making HTTP network requests 🥳
-gem "image_processing", "~> 1.14" # Set of higher-level helper methods for image processing.
-gem "jbuilder" # Build JSON APIs with ease. Read more: https://github.com/rails/jbuilder
-gem "jsbundling-rails"
-gem "lograge" # log less so heroku papertrail quits rate limiting our logs
-gem "net-imap" # needed for ruby upgrade to 3.1.0 https://www.ruby-lang.org/en/news/2021/12/25/ruby-3-1-0-released/
-gem "net-pop" # needed for ruby upgrade to 3.1.0 https://www.ruby-lang.org/en/news/2021/12/25/ruby-3-1-0-released/
-gem "net-smtp", require: false # needed for ruby upgrade to 3.1.0 for some dang reason
+gem "blueprinter" # JSON serialization
+gem "bugsnag" # Error tracking in production
+gem "caxlsx", "~> 4.2" # Excel spreadsheets - TODO can we remove this version restriction?
+gem "caxlsx_rails", "~> 0.6.4" # Excel spreadsheets - TODO can we remove this version restriction?
+gem "cssbundling-rails", "~> 1.4" # CSS compilation
+gem "delayed_job_active_record" # Background job processing
+gem "devise" # Authentication
+gem "devise_invitable" # User invitation system for Devise
+gem "draper" # Decorators for cleaner presentation logic
+gem "filterrific" # Filtering and sorting of models
+gem "flipper" # Feature flag management
+gem "flipper-active_record" # Active Record adapter for Flipper
+gem "flipper-ui" # Web UI for managing feature flags
+gem "friendly_id", "~> 5.5.1" # Allows us to use a slug instead of CASA case IDs in their URLs
+gem "groupdate" # Group data by time periods
+gem "httparty" # HTTP network requests
+gem "image_processing", "~> 1.14" # Image processing helpers
+gem "jbuilder" # JSON API builder
+gem "jsbundling-rails" # JavaScript bundling
+gem "lograge" # Log less so Heroku Papertrail quits rate limiting our logs
+gem "net-imap" # Ruby 3.1+ requires explicit inclusion of standard library gems
+gem "net-pop" # Ruby 3.1+ requires explicit inclusion of standard library gems
+gem "net-smtp", require: false # Ruby 3.1+ requires explicit inclusion of standard library gems
 gem "noticed" # Notifications
-gem "oj" # faster JSON parsing 🍊
-gem "pagy" # pagination
-gem "paranoia" # For soft-deleting database objects
-gem "pdf-forms" # filling in fund request PDFs with user input
-gem "pg" # Use postgresql as the database for Active Record
-gem "pretender"
-gem "puma", "7.0.4" # 6.2.2 fails to install on m1 # Use Puma as the app server
-gem "pundit" # for authorization management - based on user.role field
-gem "rack-attack" # for blocking & throttling abusive requests
-gem "rack-cors" # for allowing cross-origin resource sharing
-gem "request_store"
-gem "rexml" # pdf-forms needs this to deploy to heroku apparently
-gem "rswag-api"
-gem "rswag-ui"
+gem "oj" # Faster JSON parsing
+gem "pagy" # Fast and lightweight pagination
+gem "paranoia" # Soft-delete support for Active Record models
+gem "pdf-forms" # Filling in fund request PDFs with user input
+gem "pg" # Use PostgreSQL as the database for Active Record
+gem "pghero" # PostgreSQL performance monitoring and query insights
+gem "pg_query" # PostgreSQL query parser
+gem "pretender" # Allows admins to impersonate users
+gem "puma", "~> 7.0" # Use Puma as the app server
+gem "pundit" # Authorization management based on user.role field
+gem "rack-attack" # Blocking & throttling abusive requests
+gem "rack-cors" # Cross-origin resource sharing
+gem "request_store" # Per-request global storage for thread-safe data
+gem "rexml" # PDF-forms needs this to deploy to Heroku
+gem "rswag-api" # Swagger API documentation
+gem "rswag-ui" # Swagger UI
 gem "sablon" # Word document templating tool for Case Court Reports
-gem "scout_apm"
-gem "sprockets-rails" # The original asset pipeline for Rails [https://github.com/rails/sprockets-rails]
-gem "stimulus-rails"
-gem "strong_migrations"
-gem "turbo-rails", "~> 2.0"
-gem "twilio-ruby" # twilio helper functions
-gem "tzinfo-data", platforms: %i[mingw mswin x64_mingw jruby] # Windows does not include zoneinfo files, so bundle the tzinfo-data gem
+gem "scout_apm" # Application performance monitoring
+gem "scout_apm_logging", "~> 2.1" # Scout APM logging integration
+gem "sprockets-rails" # Asset pipeline for Rails
+gem "stimulus-rails" # Stimulus JavaScript framework
+gem "strong_migrations" # Catch unsafe database migrations
+gem "turbo-rails", "~> 2.0" # Turbo framework for Rails
+gem "twilio-ruby" # Twilio helper functions
+gem "tzinfo-data", platforms: %i[mingw mswin x64_mingw jruby] # Windows does not include zoneinfo files
 gem "view_component" # View components for reusability
-gem "wicked"
+gem "wicked" # Multi-step form wizard for Rails
 
-# flipper for feature flag management
-gem "flipper"
-gem "flipper-active_record"
-gem "flipper-ui"
-gem "pghero"
-gem "pg_query"
 group :development, :test do
+  gem "brakeman" # Security inspection
   gem "bullet" # Detect and fix N+1 queries
-  gem "byebug", platforms: %i[mri mingw x64_mingw] # Call 'byebug' anywhere in the code to stop execution and get a debugger console
-  gem "dotenv-rails"
-  gem "factory_bot_rails"
-  gem "parallel_tests"
-  gem "pry"
-  gem "pry-byebug"
-  gem "rspec_junit_formatter"
-  gem "rspec-rails"
-  gem "rswag-specs"
-  gem "shoulda-matchers"
-  # linters
-  gem "erb_lint", require: false
-  gem "rubocop-capybara", require: false
-  gem "rubocop-factory_bot", require: false
-  gem "rubocop-performance", require: false
-  gem "rubocop-rspec", require: false
-  gem "rubocop-rspec_rails", require: false
-  gem "standard", require: false
-  gem "standard-rails", require: false
+  gem "byebug", platforms: %i[mri mingw x64_mingw] # Debugger console
+  gem "dotenv-rails" # Environment variable management
+  gem "erb_lint", require: false # ERB linter
+  gem "factory_bot_rails" # Test data factories
+  gem "faker" # Creates realistic seed data, valuable for staging and demos
+  gem "parallel_tests" # Run tests in parallel
+  gem "pry" # Enhanced Ruby console
+  gem "pry-byebug" # Pry debugger integration
+  gem "rspec_junit_formatter" # JUnit XML formatter for RSpec
+  gem "rspec-rails" # RSpec testing framework
+  gem "rubocop-capybara", require: false # Capybara linting rules
+  gem "rubocop-factory_bot", require: false # FactoryBot linting rules
+  gem "rubocop-performance", require: false # Performance linting rules
+  gem "rubocop-rspec", require: false # RSpec linting rules
+  gem "rubocop-rspec_rails", require: false # RSpec Rails linting rules
+  gem "rswag-specs" # Swagger spec generation
+  gem "shoulda-matchers" # RSpec matchers for common Rails functionality
+  gem "standard", require: false # Ruby style guide
+  gem "standard-rails", require: false # Rails-specific style guide
 end
 
 group :development do
-  gem "annotate" # for adding db field listings to models as comments
-  gem "bundler-audit" # for checking for security issues in gems
+  gem "annotate" # Adds database field listings to models as comments
+  gem "bundler-audit" # Checks for security issues in gems
   gem "letter_opener" # Opens emails in new tab for easier testing
   gem "simplecov-mcp" # SimpleCov MCP integration
-  gem "spring" # Spring speeds up development by keeping your application running in the background. Read more: https://github.com/rails/spring
-  gem "spring-commands-rspec"
-  gem "traceroute" # for finding unused routes
-  gem "web-console", ">= 3.3.0" # Access an interactive console on exception pages or by calling 'console' anywhere in the code.
+  gem "spring" # Speeds up development by keeping your application running in the background
+  gem "spring-commands-rspec" # Spring integration for RSpec
+  gem "traceroute" # Finds unused routes
+  gem "web-console", "~> 4.0" # Interactive console on exception pages
 end
 
 group :test do
-  gem "brakeman" # security inspection
-  gem "capybara"
-  gem "rspec-retry" # for retrying flaky tests
-  gem "capybara-screenshot"
-  gem "database_cleaner-active_record"
-  gem "docx"
-  gem "email_spec"
-  gem "rails-controller-testing"
-  gem "rake"
-  gem "selenium-webdriver"
-  gem "simplecov", require: false
+  gem "capybara" # Integration testing framework
+  gem "capybara-screenshot" # Automatic screenshot on test failure
+  gem "database_cleaner-active_record" # Database cleaning strategies for tests
+  gem "docx" # For testing Word document generation
+  gem "email_spec" # Email testing helpers
+  gem "rails-controller-testing" # Controller testing helpers
+  gem "rspec-retry" # Retries flaky tests
+  gem "selenium-webdriver" # Browser automation for system tests
+  gem "simplecov", require: false # Code coverage analysis
   gem "webmock" # HTTP request stubber
 end
-
-gem "scout_apm_logging", "~> 2.1"
diff --git a/Gemfile.lock b/Gemfile.lock
index d68bfdd08a..bf6584b4fd 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -755,13 +755,12 @@ DEPENDENCIES
   pretender
   pry
   pry-byebug
-  puma (= 7.0.4)
+  puma (~> 7.0)
   pundit
   rack-attack
   rack-cors
   rails (~> 7.2)
   rails-controller-testing
-  rake
   request_store
   rexml
   rspec-rails
@@ -794,7 +793,7 @@ DEPENDENCIES
   twilio-ruby
   tzinfo-data
   view_component
-  web-console (>= 3.3.0)
+  web-console (~> 4.0)
   webmock
   wicked