diff --git a/CHANGELOG.md b/CHANGELOG.md
index 359cd177..3b16411c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,9 +14,9 @@
 * [Logging] `primary_session`, `previous_session`, and `back_to_session` now explicitly logged
 * [Sessions] The session is no longer set on update or stepping witht destination flow and state match the existing session.
 * [Scheduled Replies] The `service_message.target_id` is now set for scheduled replies. NOTE: scheduled replies that are already enqueued will NOT have this set.
-* [Server] Updated to Puma 5.5
-* [Server] Updated to Sidekiq 6.3
-* [Server] Updated to Sinatra 2.1
+* [Server] Updated to Puma 6.x
+* [Server] Updated to Sidekiq 7.x
+* [Server] Updated to Sinatra 3.x
 * [Sessions] Added `to_s` for sessions to pretty print the slug. Useful when debugging.
 * `send_reples` now supports two additional options for replies:
   `send_replies(custom_reply: 'hello/say_hello')`
diff --git a/Gemfile.lock b/Gemfile.lock
index bf7fcf9c..6e54259e 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -5,8 +5,9 @@ PATH
       activesupport (~> 7.0)
       multi_json (~> 1.12)
       puma (~> 6.0)
+      redis (~> 5.0)
       sidekiq (~> 7.0)
-      sinatra (~> 2.0)
+      sinatra (>= 2, < 4)
       thor (~> 1.0)
       zeitwerk (~> 2.6)
 
@@ -38,6 +39,8 @@ GEM
       rack
     rack-test (2.0.2)
       rack (>= 1.3)
+    redis (5.0.5)
+      redis-client (>= 0.9.0)
     redis-client (0.11.2)
       connection_pool
     rspec (3.12.0)
diff --git a/lib/stealth/base.rb b/lib/stealth/base.rb
index 31fbbcee..0f0585d4 100644
--- a/lib/stealth/base.rb
+++ b/lib/stealth/base.rb
@@ -4,6 +4,7 @@
 # base requirements
 require 'yaml'
 require 'sidekiq'
+require 'redis'
 require 'active_support/all'
 
 begin
@@ -123,7 +124,9 @@ def self.load_environment
 
     load_bot!
 
-    Sidekiq[:reloader] = Stealth.bot_reloader
+    Sidekiq.configure_server do |config|
+      config[:reloader] = Stealth.bot_reloader
+    end
 
     if defined?(ActiveRecord)
       if ENV['DATABASE_URL'].present?
@@ -131,7 +134,7 @@ def self.load_environment
       else
         database_config = File.read(File.join(Stealth.root, 'config', 'database.yml'))
         ActiveRecord::Base.establish_connection(
-          YAML.load(ERB.new(database_config).result)[Stealth.env]
+          YAML.load(ERB.new(database_config).result, aliases: true)[Stealth.env]
         )
       end
     end
diff --git a/lib/stealth/generators/builder/Gemfile b/lib/stealth/generators/builder/Gemfile
index c849c39e..b6b64579 100644
--- a/lib/stealth/generators/builder/Gemfile
+++ b/lib/stealth/generators/builder/Gemfile
@@ -2,8 +2,8 @@ source 'https://rubygems.org'
 
 gem 'stealth', '~> 2.0'
 
-gem 'railties', '~> 6.0'
-gem 'activerecord', '~> 6.0'
+gem 'railties', '~> 7.0'
+gem 'activerecord', '~> 7.0'
 # Use sqlite3 as the database for Active Record
 gem 'sqlite3'
 
diff --git a/stealth.gemspec b/stealth.gemspec
index f3ac8bec..67427d1e 100644
--- a/stealth.gemspec
+++ b/stealth.gemspec
@@ -12,12 +12,13 @@ Gem::Specification.new do |s|
   s.authors = ['Mauricio Gomes', 'Matthew Black']
   s.email = 'mauricio@edge14.com'
 
-  s.add_dependency 'sinatra', '~> 2.0'
-  s.add_dependency 'puma', '~> 6.0'
-  s.add_dependency 'thor', '~> 1.0'
+  s.add_dependency 'activesupport', '~> 7.0'
   s.add_dependency 'multi_json', '~> 1.12'
+  s.add_dependency 'puma', '~> 6.0'
+  s.add_dependency 'redis', '~> 5.0'
   s.add_dependency 'sidekiq', '~> 7.0'
-  s.add_dependency 'activesupport', '~> 7.0'
+  s.add_dependency 'sinatra', '>= 2', '< 4'
+  s.add_dependency 'thor', '~> 1.0'
   s.add_dependency 'zeitwerk', '~> 2.6'
 
   s.add_development_dependency 'rspec', '~> 3.9'