diff --git a/.rubocop.yml b/.rubocop.yml
index 64021b4cec9..69989411443 100644
--- a/.rubocop.yml
+++ b/.rubocop.yml
@@ -96,12 +96,11 @@ Rails/FilePath:
 Rails/HttpStatus:
   EnforcedStyle: numeric
 
-# Reason: Allowed in `tootctl` CLI code and in boot ENV checker
+# Reason: Allowed in boot ENV checker
 # https://docs.rubocop.org/rubocop-rails/cops_rails.html#railsexit
 Rails/Exit:
   Exclude:
     - 'config/boot.rb'
-    - 'lib/mastodon/cli/*.rb'
 
 # Reason: Conflicts with `Lint/UselessMethodDefinition` for inherited controller actions
 # https://docs.rubocop.org/rubocop-rails/cops_rails.html#railslexicallyscopedactionfilter
diff --git a/bin/tootctl b/bin/tootctl
index b3311c6b2a3..ff64eb2e42c 100755
--- a/bin/tootctl
+++ b/bin/tootctl
@@ -6,8 +6,13 @@ require_relative '../lib/mastodon/cli/main'
 
 begin
   Chewy.strategy(:mastodon) do
-    Mastodon::CLI::Main.start(ARGV)
+    Mastodon::CLI::Main.start(ARGV, debug: true) # Enables the script to rescue `Thor::Error`
   end
+rescue Thor::Error => e
+  Thor::Shell::Color
+    .new
+    .say_error(e.message, :red)
+  exit(1)
 rescue Interrupt
   exit(130)
 end
diff --git a/lib/mastodon/cli/accounts.rb b/lib/mastodon/cli/accounts.rb
index 9dc65c1477d..b5308e2b762 100644
--- a/lib/mastodon/cli/accounts.rb
+++ b/lib/mastodon/cli/accounts.rb
@@ -39,8 +39,7 @@ module Mastodon::CLI
         rotate_keys_for_account(Account.find_local(username))
         say('OK', :green)
       else
-        say('No account(s) given', :red)
-        exit(1)
+        fail_with_message 'No account(s) given'
       end
     end
 
@@ -74,10 +73,7 @@ module Mastodon::CLI
       if options[:role]
         role = UserRole.find_by(name: options[:role])
 
-        if role.nil?
-          say('Cannot find user role with that name', :red)
-          exit(1)
-        end
+        fail_with_message 'Cannot find user role with that name' if role.nil?
 
         role_id = role.id
       end
@@ -114,7 +110,6 @@ module Mastodon::CLI
         say("New password: #{password}")
       else
         report_errors(user.errors)
-        exit(1)
       end
     end
 
@@ -152,18 +147,12 @@ module Mastodon::CLI
     def modify(username)
       user = Account.find_local(username)&.user
 
-      if user.nil?
-        say('No user with such username', :red)
-        exit(1)
-      end
+      fail_with_message 'No user with such username' if user.nil?
 
       if options[:role]
         role = UserRole.find_by(name: options[:role])
 
-        if role.nil?
-          say('Cannot find user role with that name', :red)
-          exit(1)
-        end
+        fail_with_message 'Cannot find user role with that name' if role.nil?
 
         user.role_id = role.id
       elsif options[:remove_role]
@@ -185,7 +174,6 @@ module Mastodon::CLI
         say("New password: #{password}") if options[:reset_password]
       else
         report_errors(user.errors)
-        exit(1)
       end
     end
 
@@ -200,27 +188,19 @@ module Mastodon::CLI
     LONG_DESC
     def delete(username = nil)
       if username.present? && options[:email].present?
-        say('Use username or --email, not both', :red)
-        exit(1)
+        fail_with_message  'Use username or --email, not both'
       elsif username.blank? && options[:email].blank?
-        say('No username provided', :red)
-        exit(1)
+        fail_with_message 'No username provided'
       end
 
       account = nil
 
       if username.present?
         account = Account.find_local(username)
-        if account.nil?
-          say('No user with such username', :red)
-          exit(1)
-        end
+        fail_with_message 'No user with such username' if account.nil?
       else
         account = Account.left_joins(:user).find_by(user: { email: options[:email] })
-        if account.nil?
-          say('No user with such email', :red)
-          exit(1)
-        end
+        fail_with_message 'No user with such email' if account.nil?
       end
 
       say("Deleting user with #{account.statuses_count} statuses, this might take a while...#{dry_run_mode_suffix}")
@@ -243,23 +223,18 @@ module Mastodon::CLI
       username, domain = from_acct.split('@')
       from_account = Account.find_remote(username, domain)
 
-      if from_account.nil? || from_account.local?
-        say("No such account (#{from_acct})", :red)
-        exit(1)
-      end
+      fail_with_message "No such account (#{from_acct})" if from_account.nil? || from_account.local?
 
       username, domain = to_acct.split('@')
       to_account = Account.find_remote(username, domain)
 
-      if to_account.nil? || to_account.local?
-        say("No such account (#{to_acct})", :red)
-        exit(1)
-      end
+      fail_with_message "No such account (#{to_acct})" if to_account.nil? || to_account.local?
 
       if from_account.public_key != to_account.public_key && !options[:force]
-        say("Accounts don't have the same public key, might not be duplicates!", :red)
-        say('Override with --force', :red)
-        exit(1)
+        fail_with_message <<~ERROR
+          Accounts don't have the same public key, might not be duplicates!
+          Override with --force
+        ERROR
       end
 
       to_account.merge_with!(from_account)
@@ -298,10 +273,7 @@ module Mastodon::CLI
     def backup(username)
       account = Account.find_local(username)
 
-      if account.nil?
-        say('No user with such username', :red)
-        exit(1)
-      end
+      fail_with_message 'No user with such username' if account.nil?
 
       backup = account.user.backups.create!
       BackupWorker.perform_async(backup.id)
@@ -387,10 +359,7 @@ module Mastodon::CLI
           user, domain = user.split('@')
           account = Account.find_remote(user, domain)
 
-          if account.nil?
-            say('No such account', :red)
-            exit(1)
-          end
+          fail_with_message 'No such account' if account.nil?
 
           next if dry_run?
 
@@ -405,8 +374,7 @@ module Mastodon::CLI
 
         say("OK#{dry_run_mode_suffix}", :green)
       else
-        say('No account(s) given', :red)
-        exit(1)
+        fail_with_message 'No account(s) given'
       end
     end
 
@@ -416,10 +384,7 @@ module Mastodon::CLI
     def follow(username)
       target_account = Account.find_local(username)
 
-      if target_account.nil?
-        say('No such account', :red)
-        exit(1)
-      end
+      fail_with_message 'No such account' if target_account.nil?
 
       processed, = parallelize_with_progress(Account.local.without_suspended) do |account|
         FollowService.new.call(account, target_account, bypass_limit: true)
@@ -435,10 +400,7 @@ module Mastodon::CLI
       username, domain = acct.split('@')
       target_account = Account.find_remote(username, domain)
 
-      if target_account.nil?
-        say('No such account', :red)
-        exit(1)
-      end
+      fail_with_message 'No such account' if target_account.nil?
 
       processed, = parallelize_with_progress(target_account.followers.local) do |account|
         UnfollowService.new.call(account, target_account)
@@ -459,17 +421,11 @@ module Mastodon::CLI
       With the --followers option, the command removes all followers of the account.
     LONG_DESC
     def reset_relationships(username)
-      unless options[:follows] || options[:followers]
-        say('Please specify either --follows or --followers, or both', :red)
-        exit(1)
-      end
+      fail_with_message 'Please specify either --follows or --followers, or both' unless options[:follows] || options[:followers]
 
       account = Account.find_local(username)
 
-      if account.nil?
-        say('No such account', :red)
-        exit(1)
-      end
+      fail_with_message 'No such account' if account.nil?
 
       total     = 0
       total    += account.following.reorder(nil).count if options[:follows]
@@ -515,6 +471,8 @@ module Mastodon::CLI
       account identified by its username.
     LONG_DESC
     def approve(username = nil)
+      fail_with_message 'Number must be positive' if options[:number]&.negative?
+
       if options[:all]
         User.pending.find_each(&:approve!)
         say('OK', :green)
@@ -524,16 +482,10 @@ module Mastodon::CLI
       elsif username.present?
         account = Account.find_local(username)
 
-        if account.nil?
-          say('No such account', :red)
-          exit(1)
-        end
+        fail_with_message 'No such account' if account.nil?
 
         account.user&.approve!
         say('OK', :green)
-      else
-        say('Number must be positive', :red) if options[:number]
-        exit(1)
       end
     end
 
@@ -587,56 +539,34 @@ module Mastodon::CLI
       redirects to a different account that the one specified.
     LONG_DESC
     def migrate(username)
-      if options[:replay].present? && options[:target].present?
-        say('Use --replay or --target, not both', :red)
-        exit(1)
-      end
+      fail_with_message 'Use --replay or --target, not both' if options[:replay].present? && options[:target].present?
 
-      if options[:replay].blank? && options[:target].blank?
-        say('Use either --replay or --target', :red)
-        exit(1)
-      end
+      fail_with_message 'Use either --replay or --target' if options[:replay].blank? && options[:target].blank?
 
       account = Account.find_local(username)
 
-      if account.nil?
-        say("No such account: #{username}", :red)
-        exit(1)
-      end
+      fail_with_message "No such account: #{username}" if account.nil?
 
       migration = nil
 
       if options[:replay]
         migration = account.migrations.last
-        if migration.nil?
-          say('The specified account has not performed any migration', :red)
-          exit(1)
-        end
+        fail_with_message 'The specified account has not performed any migration' if migration.nil?
 
-        unless options[:force] || migration.target_account_id == account.moved_to_account_id
-          say('The specified account is not redirecting to its last migration target. Use --force if you want to replay the migration anyway', :red)
-          exit(1)
-        end
+        fail_with_message 'The specified account is not redirecting to its last migration target. Use --force if you want to replay the migration anyway' unless options[:force] || migration.target_account_id == account.moved_to_account_id
       end
 
       if options[:target]
         target_account = ResolveAccountService.new.call(options[:target])
 
-        if target_account.nil?
-          say("The specified target account could not be found: #{options[:target]}", :red)
-          exit(1)
-        end
+        fail_with_message "The specified target account could not be found: #{options[:target]}" if target_account.nil?
 
-        unless options[:force] || account.moved_to_account_id.nil? || account.moved_to_account_id == target_account.id
-          say('The specified account is redirecting to a different target account. Use --force if you want to change the migration target', :red)
-          exit(1)
-        end
+        fail_with_message 'The specified account is redirecting to a different target account. Use --force if you want to change the migration target' unless options[:force] || account.moved_to_account_id.nil? || account.moved_to_account_id == target_account.id
 
         begin
           migration = account.migrations.create!(acct: target_account.acct)
         rescue ActiveRecord::RecordInvalid => e
-          say("Error: #{e.message}", :red)
-          exit(1)
+          fail_with_message "Error: #{e.message}"
         end
       end
 
@@ -648,18 +578,18 @@ module Mastodon::CLI
     private
 
     def report_errors(errors)
-      errors.each do |error|
-        say('Failure/Error: ', :red)
-        say(error.attribute)
-        say("    #{error.type}", :red)
-      end
+      message = errors.map do |error|
+        <<~STRING
+          Failure/Error: #{error.attribute}
+              #{error.type}
+        STRING
+      end.join
+
+      fail_with_message message
     end
 
     def rotate_keys_for_account(account, delay = 0)
-      if account.nil?
-        say('No such account', :red)
-        exit(1)
-      end
+      fail_with_message 'No such account' if account.nil?
 
       old_key = account.private_key
       new_key = OpenSSL::PKey::RSA.new(2048)
diff --git a/lib/mastodon/cli/base.rb b/lib/mastodon/cli/base.rb
index 8c222bbb2b3..93dec1fb8fe 100644
--- a/lib/mastodon/cli/base.rb
+++ b/lib/mastodon/cli/base.rb
@@ -18,6 +18,10 @@ module Mastodon
 
       private
 
+      def fail_with_message(message)
+        raise Thor::Error, message
+      end
+
       def pastel
         @pastel ||= Pastel.new
       end
diff --git a/lib/mastodon/cli/cache.rb b/lib/mastodon/cli/cache.rb
index e8a2ac1610a..f32ab292ee2 100644
--- a/lib/mastodon/cli/cache.rb
+++ b/lib/mastodon/cli/cache.rb
@@ -31,8 +31,7 @@ module Mastodon::CLI
           recount_status_stats(status)
         end
       else
-        say("Unknown type: #{type}", :red)
-        exit(1)
+        fail_with_message "Unknown type: #{type}"
       end
 
       say
diff --git a/lib/mastodon/cli/domains.rb b/lib/mastodon/cli/domains.rb
index e092497dc9e..c247463af52 100644
--- a/lib/mastodon/cli/domains.rb
+++ b/lib/mastodon/cli/domains.rb
@@ -41,11 +41,9 @@ module Mastodon::CLI
 
       # Sanity check on command arguments
       if options[:limited_federation_mode] && !domains.empty?
-        say('DOMAIN parameter not supported with --limited-federation-mode', :red)
-        exit(1)
+        fail_with_message 'DOMAIN parameter not supported with --limited-federation-mode'
       elsif domains.empty? && !options[:limited_federation_mode]
-        say('No domain(s) given', :red)
-        exit(1)
+        fail_with_message 'No domain(s) given'
       end
 
       # Build scopes from command arguments
diff --git a/lib/mastodon/cli/email_domain_blocks.rb b/lib/mastodon/cli/email_domain_blocks.rb
index 022b1dcbb17..6b9107c8ade 100644
--- a/lib/mastodon/cli/email_domain_blocks.rb
+++ b/lib/mastodon/cli/email_domain_blocks.rb
@@ -30,10 +30,7 @@ module Mastodon::CLI
       it at the root.
     LONG_DESC
     def add(*domains)
-      if domains.empty?
-        say('No domain(s) given', :red)
-        exit(1)
-      end
+      fail_with_message 'No domain(s) given' if domains.empty?
 
       skipped = 0
       processed = 0
@@ -76,10 +73,7 @@ module Mastodon::CLI
 
     desc 'remove DOMAIN...', 'Remove e-mail domain blocks'
     def remove(*domains)
-      if domains.empty?
-        say('No domain(s) given', :red)
-        exit(1)
-      end
+      fail_with_message 'No domain(s) given' if domains.empty?
 
       skipped = 0
       processed = 0
diff --git a/lib/mastodon/cli/emoji.rb b/lib/mastodon/cli/emoji.rb
index 912c0991240..4a8949de0e4 100644
--- a/lib/mastodon/cli/emoji.rb
+++ b/lib/mastodon/cli/emoji.rb
@@ -86,14 +86,8 @@ module Mastodon::CLI
       category         = CustomEmojiCategory.find_by(name: options[:category])
       export_file_name = File.join(path, 'export.tar.gz')
 
-      if File.file?(export_file_name) && !options[:overwrite]
-        say("Archive already exists! Use '--overwrite' to overwrite it!")
-        exit 1
-      end
-      if category.nil? && options[:category]
-        say("Unable to find category '#{options[:category]}'!")
-        exit 1
-      end
+      fail_with_message "Archive already exists! Use '--overwrite' to overwrite it!" if File.file?(export_file_name) && !options[:overwrite]
+      fail_with_message "Unable to find category '#{options[:category]}'!" if category.nil? && options[:category]
 
       File.open(export_file_name, 'wb') do |file|
         Zlib::GzipWriter.wrap(file) do |gzip|
diff --git a/lib/mastodon/cli/federation.rb b/lib/mastodon/cli/federation.rb
index 8bb46ecb1ae..c7387965573 100644
--- a/lib/mastodon/cli/federation.rb
+++ b/lib/mastodon/cli/federation.rb
@@ -43,10 +43,10 @@ module Mastodon::CLI
             say('Every deletion notice has been sent! You can safely delete all data and decomission your servers!', :green)
           end
 
-          exit(0)
+          raise(SystemExit)
         end
 
-        exit(1) unless ask('Type in the domain of the server to confirm:') == Rails.configuration.x.local_domain
+        fail_with_message 'Domains do not match. Stopping self-destruct initiation.' unless domain_match_confirmed?
 
         say(<<~WARNING, :yellow)
           This operation WILL NOT be reversible.
@@ -54,19 +54,25 @@ module Mastodon::CLI
           The deletion process itself may take a long time, and will be handled by Sidekiq, so do not shut it down until it has finished (you will be able to re-run this command to see the state of the self-destruct process).
         WARNING
 
-        exit(1) if no?('Are you sure you want to proceed?')
+        fail_with_message 'Operation cancelled. Self-destruct will not begin.' if proceed_prompt_negative?
 
         say(<<~INSTRUCTIONS, :green)
           To switch Mastodon to self-destruct mode, add the following variable to your evironment (e.g. by adding a line to your `.env.production`) and restart all Mastodon processes:
             SELF_DESTRUCT=#{self_destruct_value}
           You can re-run this command to see the state of the self-destruct process.
         INSTRUCTIONS
-      rescue Interrupt
-        exit(1)
       end
 
       private
 
+      def domain_match_confirmed?
+        ask('Type in the domain of the server to confirm:') == Rails.configuration.x.local_domain
+      end
+
+      def proceed_prompt_negative?
+        no?('Are you sure you want to proceed?')
+      end
+
       def self_destruct_value
         Rails
           .application
diff --git a/lib/mastodon/cli/feeds.rb b/lib/mastodon/cli/feeds.rb
index 3467dd427cf..39affd5e8ee 100644
--- a/lib/mastodon/cli/feeds.rb
+++ b/lib/mastodon/cli/feeds.rb
@@ -27,17 +27,13 @@ module Mastodon::CLI
       elsif username.present?
         account = Account.find_local(username)
 
-        if account.nil?
-          say('No such account', :red)
-          exit(1)
-        end
+        fail_with_message 'No such account' if account.nil?
 
         PrecomputeFeedService.new.call(account) unless dry_run?
 
         say("OK #{dry_run_mode_suffix}", :green, true)
       else
-        say('No account(s) given', :red)
-        exit(1)
+        fail_with_message 'No account(s) given'
       end
     end
 
diff --git a/lib/mastodon/cli/ip_blocks.rb b/lib/mastodon/cli/ip_blocks.rb
index d12919c3601..100bf7bada5 100644
--- a/lib/mastodon/cli/ip_blocks.rb
+++ b/lib/mastodon/cli/ip_blocks.rb
@@ -20,10 +20,7 @@ module Mastodon::CLI
       option to overwrite it.
     LONG_DESC
     def add(*addresses)
-      if addresses.empty?
-        say('No IP(s) given', :red)
-        exit(1)
-      end
+      fail_with_message 'No IP(s) given' if addresses.empty?
 
       skipped   = 0
       processed = 0
@@ -70,10 +67,7 @@ module Mastodon::CLI
       cover the given IP(s).
     LONG_DESC
     def remove(*addresses)
-      if addresses.empty?
-        say('No IP(s) given', :red)
-        exit(1)
-      end
+      fail_with_message 'No IP(s) given' if addresses.empty?
 
       processed = 0
       skipped   = 0
diff --git a/lib/mastodon/cli/maintenance.rb b/lib/mastodon/cli/maintenance.rb
index a64206065d5..9f234e38603 100644
--- a/lib/mastodon/cli/maintenance.rb
+++ b/lib/mastodon/cli/maintenance.rb
@@ -199,26 +199,24 @@ module Mastodon::CLI
 
     def verify_schema_version!
       if migrator_version < MIN_SUPPORTED_VERSION
-        say 'Your version of the database schema is too old and is not supported by this script.', :red
-        say 'Please update to at least Mastodon 3.0.0 before running this script.', :red
-        exit(1)
+        fail_with_message <<~ERROR
+          Your version of the database schema is too old and is not supported by this script.
+          Please update to at least Mastodon 3.0.0 before running this script.
+        ERROR
       elsif migrator_version > MAX_SUPPORTED_VERSION
         say 'Your version of the database schema is more recent than this script, this may cause unexpected errors.', :yellow
-        exit(1) unless yes?('Continue anyway? (Yes/No)')
+        fail_with_message 'Stopping maintenance script because data is more recent than script version.' unless yes?('Continue anyway? (Yes/No)')
       end
     end
 
     def verify_sidekiq_not_active!
-      if Sidekiq::ProcessSet.new.any?
-        say 'It seems Sidekiq is running. All Mastodon processes need to be stopped when using this script.', :red
-        exit(1)
-      end
+      fail_with_message 'It seems Sidekiq is running. All Mastodon processes need to be stopped when using this script.' if Sidekiq::ProcessSet.new.any?
     end
 
     def verify_backup_warning!
       say 'This task will take a long time to run and is potentially destructive.', :yellow
       say 'Please make sure to stop Mastodon and have a backup.', :yellow
-      exit(1) unless yes?('Continue? (Yes/No)')
+      fail_with_message 'Maintenance process stopped.' unless yes?('Continue? (Yes/No)')
     end
 
     def deduplicate_accounts!
diff --git a/lib/mastodon/cli/media.rb b/lib/mastodon/cli/media.rb
index a796bb729a7..87946e0262f 100644
--- a/lib/mastodon/cli/media.rb
+++ b/lib/mastodon/cli/media.rb
@@ -31,15 +31,9 @@ module Mastodon::CLI
       following anyone locally are pruned.
     DESC
     def remove
-      if options[:prune_profiles] && options[:remove_headers]
-        say('--prune-profiles and --remove-headers should not be specified simultaneously', :red, true)
-        exit(1)
-      end
+      fail_with_message '--prune-profiles and --remove-headers should not be specified simultaneously' if options[:prune_profiles] && options[:remove_headers]
 
-      if options[:include_follows] && !(options[:prune_profiles] || options[:remove_headers])
-        say('--include-follows can only be used with --prune-profiles or --remove-headers', :red, true)
-        exit(1)
-      end
+      fail_with_message '--include-follows can only be used with --prune-profiles or --remove-headers' if options[:include_follows] && !(options[:prune_profiles] || options[:remove_headers])
       time_ago = options[:days].days.ago
 
       if options[:prune_profiles] || options[:remove_headers]
@@ -156,11 +150,9 @@ module Mastodon::CLI
           end
         end
       when :fog
-        say('The fog storage driver is not supported for this operation at this time', :red)
-        exit(1)
+        fail_with_message 'The fog storage driver is not supported for this operation at this time'
       when :azure
-        say('The azure storage driver is not supported for this operation at this time', :red)
-        exit(1)
+        fail_with_message 'The azure storage driver is not supported for this operation at this time'
       when :filesystem
         require 'find'
 
@@ -254,10 +246,7 @@ module Mastodon::CLI
         username, domain = options[:account].split('@')
         account = Account.find_remote(username, domain)
 
-        if account.nil?
-          say('No such account', :red)
-          exit(1)
-        end
+        fail_with_message 'No such account' if account.nil?
 
         scope = MediaAttachment.where(account_id: account.id)
       elsif options[:domain]
@@ -265,8 +254,7 @@ module Mastodon::CLI
       elsif options[:days].present?
         scope = MediaAttachment.remote
       else
-        say('Specify the source of media attachments', :red)
-        exit(1)
+        fail_with_message 'Specify the source of media attachments'
       end
 
       scope = scope.where('media_attachments.id > ?', Mastodon::Snowflake.id_at(options[:days].days.ago, with_random: false)) if options[:days].present?
@@ -306,38 +294,25 @@ module Mastodon::CLI
       path_segments = path.split('/')[2..]
       path_segments.delete('cache')
 
-      unless VALID_PATH_SEGMENTS_SIZE.include?(path_segments.size)
-        say('Not a media URL', :red)
-        exit(1)
-      end
+      fail_with_message 'Not a media URL' unless VALID_PATH_SEGMENTS_SIZE.include?(path_segments.size)
 
       model_name = path_segments.first.classify
       record_id  = path_segments[2..-2].join.to_i
 
-      unless PRELOAD_MODEL_WHITELIST.include?(model_name)
-        say("Cannot find corresponding model: #{model_name}", :red)
-        exit(1)
-      end
+      fail_with_message "Cannot find corresponding model: #{model_name}" unless PRELOAD_MODEL_WHITELIST.include?(model_name)
 
       record = model_name.constantize.find_by(id: record_id)
       record = record.status if record.respond_to?(:status)
 
-      unless record
-        say('Cannot find corresponding record', :red)
-        exit(1)
-      end
+      fail_with_message 'Cannot find corresponding record' unless record
 
       display_url = ActivityPub::TagManager.instance.url_for(record)
 
-      if display_url.blank?
-        say('No public URL for this type of record', :red)
-        exit(1)
-      end
+      fail_with_message 'No public URL for this type of record' if display_url.blank?
 
       say(display_url, :blue)
     rescue Addressable::URI::InvalidURIError
-      say('Invalid URL', :red)
-      exit(1)
+      fail_with_message 'Invalid URL'
     end
 
     private
diff --git a/lib/mastodon/cli/progress_helper.rb b/lib/mastodon/cli/progress_helper.rb
index 1fa2745c180..4fcc47a7f74 100644
--- a/lib/mastodon/cli/progress_helper.rb
+++ b/lib/mastodon/cli/progress_helper.rb
@@ -25,10 +25,7 @@ module Mastodon::CLI
     end
 
     def parallelize_with_progress(scope)
-      if options[:concurrency] < 1
-        say('Cannot run with this concurrency setting, must be at least 1', :red)
-        exit(1)
-      end
+      fail_with_message 'Cannot run with this concurrency setting, must be at least 1' if options[:concurrency] < 1
 
       reset_connection_pools!
 
diff --git a/lib/mastodon/cli/search.rb b/lib/mastodon/cli/search.rb
index 77c455f0498..5901c07776b 100644
--- a/lib/mastodon/cli/search.rb
+++ b/lib/mastodon/cli/search.rb
@@ -110,17 +110,11 @@ module Mastodon::CLI
     end
 
     def verify_deploy_concurrency!
-      return unless options[:concurrency] < 1
-
-      say('Cannot run with this concurrency setting, must be at least 1', :red)
-      exit(1)
+      fail_with_message 'Cannot run with this concurrency setting, must be at least 1' if options[:concurrency] < 1
     end
 
     def verify_deploy_batch_size!
-      return unless options[:batch_size] < 1
-
-      say('Cannot run with this batch_size setting, must be at least 1', :red)
-      exit(1)
+      fail_with_message 'Cannot run with this batch_size setting, must be at least 1' if options[:batch_size] < 1
     end
 
     def progress_output_options
diff --git a/lib/mastodon/cli/statuses.rb b/lib/mastodon/cli/statuses.rb
index 48d76e02885..57b03c941c4 100644
--- a/lib/mastodon/cli/statuses.rb
+++ b/lib/mastodon/cli/statuses.rb
@@ -26,10 +26,7 @@ module Mastodon::CLI
       indices before commencing, and removes them afterward.
     LONG_DESC
     def remove
-      if options[:batch_size] < 1
-        say('Cannot run with this batch_size setting, must be at least 1', :red)
-        exit(1)
-      end
+      fail_with_message 'Cannot run with this batch_size setting, must be at least 1' if options[:batch_size] < 1
 
       remove_statuses
       vacuum_and_analyze_statuses
diff --git a/lib/mastodon/cli/upgrade.rb b/lib/mastodon/cli/upgrade.rb
index cf839868448..2cb51057948 100644
--- a/lib/mastodon/cli/upgrade.rb
+++ b/lib/mastodon/cli/upgrade.rb
@@ -103,13 +103,11 @@ module Mastodon::CLI
     end
 
     def upgrade_storage_fog(_progress, _attachment, _style)
-      say('The fog storage driver is not supported for this operation at this time', :red)
-      exit(1)
+      fail_with_message 'The fog storage driver is not supported for this operation at this time'
     end
 
     def upgrade_storage_azure(_progress, _attachment, _style)
-      say('The azure storage driver is not supported for this operation at this time', :red)
-      exit(1)
+      fail_with_message 'The azure storage driver is not supported for this operation at this time'
     end
 
     def upgrade_storage_filesystem(progress, attachment, style)
diff --git a/spec/lib/mastodon/cli/accounts_spec.rb b/spec/lib/mastodon/cli/accounts_spec.rb
index 26ad983bbce..98be2b2027d 100644
--- a/spec/lib/mastodon/cli/accounts_spec.rb
+++ b/spec/lib/mastodon/cli/accounts_spec.rb
@@ -65,8 +65,7 @@ describe Mastodon::CLI::Accounts do
 
           it 'exits with an error message' do
             expect { subject }
-              .to output_results('Failure/Error: email')
-              .and raise_error(SystemExit)
+              .to raise_error(Thor::Error, %r{Failure/Error: email})
           end
         end
       end
@@ -127,8 +126,7 @@ describe Mastodon::CLI::Accounts do
 
           it 'exits with an error message indicating the role name was not found' do
             expect { subject }
-              .to output_results('Cannot find user role with that name')
-              .and raise_error(SystemExit)
+              .to raise_error(Thor::Error, 'Cannot find user role with that name')
           end
         end
       end
@@ -191,8 +189,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating the user was not found' do
         expect { subject }
-          .to output_results('No user with such username')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No user with such username')
       end
     end
 
@@ -214,8 +211,7 @@ describe Mastodon::CLI::Accounts do
 
           it 'exits with an error message indicating the role was not found' do
             expect { subject }
-              .to output_results('Cannot find user role with that name')
-              .and raise_error(SystemExit)
+              .to raise_error(Thor::Error, 'Cannot find user role with that name')
           end
         end
 
@@ -364,8 +360,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message' do
           expect { subject }
-            .to output_results('Failure/Error: email')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, %r{Failure/Error: email})
         end
       end
     end
@@ -387,16 +382,14 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that only one should be used' do
         expect { subject }
-          .to output_results('Use username or --email, not both')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'Use username or --email, not both')
       end
     end
 
     context 'when neither username nor --email are provided' do
       it 'exits with an error message indicating that no username was provided' do
         expect { subject }
-          .to output_results('No username provided')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No username provided')
       end
     end
 
@@ -425,8 +418,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message indicating that no user was found' do
           expect { subject }
-            .to output_results('No user with such username')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'No user with such username')
         end
       end
     end
@@ -458,8 +450,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message indicating that no user was found' do
           expect { subject }
-            .to output_results('No user with such email')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'No user with such email')
         end
       end
     end
@@ -511,8 +502,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message indicating that the number must be positive' do
           expect { subject }
-            .to output_results('Number must be positive')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'Number must be positive')
         end
       end
 
@@ -545,8 +535,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message indicating that no such account was found' do
           expect { subject }
-            .to output_results('No such account')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'No such account')
         end
       end
     end
@@ -560,8 +549,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that no account with the given username was found' do
         expect { subject }
-          .to output_results('No such account')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No such account')
       end
     end
 
@@ -596,8 +584,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that no account with the given username was found' do
         expect { subject }
-          .to output_results('No such account')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No such account')
       end
     end
 
@@ -634,8 +621,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that there is no such account' do
         expect { subject }
-          .to output_results('No user with such username')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No user with such username')
       end
     end
 
@@ -795,8 +781,7 @@ describe Mastodon::CLI::Accounts do
           allow(Account).to receive(:find_remote).with(account_example_com_b.username, account_example_com_b.domain).and_return(nil)
 
           expect { subject }
-            .to output_results('No such account')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'No such account')
         end
       end
 
@@ -892,8 +877,7 @@ describe Mastodon::CLI::Accounts do
     context 'when neither a list of accts nor options are provided' do
       it 'exits with an error message' do
         expect { subject }
-          .to output_results('No account(s) given')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No account(s) given')
       end
     end
   end
@@ -904,8 +888,7 @@ describe Mastodon::CLI::Accounts do
     context 'when neither username nor --all option are given' do
       it 'exits with an error message' do
         expect { subject }
-          .to output_results('No account(s) given')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No account(s) given')
       end
     end
 
@@ -940,8 +923,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message when the specified username is not found' do
         expect { subject }
-          .to output_results('No such account')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No such account')
       end
     end
 
@@ -980,8 +962,7 @@ describe Mastodon::CLI::Accounts do
     shared_examples 'an account not found' do |acct|
       it 'exits with an error message indicating that there is no such account' do
         expect { subject }
-          .to output_results("No such account (#{acct})")
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, "No such account (#{acct})")
       end
     end
 
@@ -1031,8 +1012,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that the accounts do not have the same pub key' do
         expect { subject }
-          .to output_results("Accounts don't have the same public key, might not be duplicates!\nOverride with --force")
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, "Accounts don't have the same public key, might not be duplicates!\nOverride with --force\n")
       end
 
       context 'with --force option' do
@@ -1200,8 +1180,7 @@ describe Mastodon::CLI::Accounts do
     context 'when no option is given' do
       it 'exits with an error message indicating that at least one option is required' do
         expect { subject }
-          .to output_results('Please specify either --follows or --followers, or both')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'Please specify either --follows or --followers, or both')
       end
     end
 
@@ -1211,8 +1190,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that there is no such account' do
         expect { subject }
-          .to output_results('No such account')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No such account')
       end
     end
 
@@ -1368,16 +1346,14 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that using both options is not possible' do
         expect { subject }
-          .to output_results('Use --replay or --target, not both')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'Use --replay or --target, not both')
       end
     end
 
     context 'when no option is given' do
       it 'exits with an error message indicating that at least one option must be used' do
         expect { subject }
-          .to output_results('Use either --replay or --target')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'Use either --replay or --target')
       end
     end
 
@@ -1387,8 +1363,7 @@ describe Mastodon::CLI::Accounts do
 
       it 'exits with an error message indicating that there is no such account' do
         expect { subject }
-          .to output_results("No such account: #{arguments.first}")
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, "No such account: #{arguments.first}")
       end
     end
 
@@ -1398,8 +1373,7 @@ describe Mastodon::CLI::Accounts do
       context 'when the specified account has no previous migrations' do
         it 'exits with an error message indicating that the given account has no previous migrations' do
           expect { subject }
-            .to output_results('The specified account has not performed any migration')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'The specified account has not performed any migration')
         end
       end
 
@@ -1421,8 +1395,7 @@ describe Mastodon::CLI::Accounts do
 
           it 'exits with an error message' do
             expect { subject }
-              .to output_results('The specified account is not redirecting to its last migration target. Use --force if you want to replay the migration anyway')
-              .and raise_error(SystemExit)
+              .to raise_error(Thor::Error, 'The specified account is not redirecting to its last migration target. Use --force if you want to replay the migration anyway')
           end
         end
 
@@ -1449,8 +1422,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message indicating that there is no such account' do
           expect { subject }
-            .to output_results("The specified target account could not be found: #{options[:target]}")
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, "The specified target account could not be found: #{options[:target]}")
         end
       end
 
@@ -1474,8 +1446,7 @@ describe Mastodon::CLI::Accounts do
       context 'when the migration record is invalid' do
         it 'exits with an error indicating that the validation failed' do
           expect { subject }
-            .to output_results('Error: Validation failed')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, /Error: Validation failed/)
         end
       end
 
@@ -1486,8 +1457,7 @@ describe Mastodon::CLI::Accounts do
 
         it 'exits with an error message' do
           expect { subject }
-            .to output_results('The specified account is redirecting to a different target account. Use --force if you want to change the migration target')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'The specified account is redirecting to a different target account. Use --force if you want to change the migration target')
         end
       end
 
diff --git a/spec/lib/mastodon/cli/cache_spec.rb b/spec/lib/mastodon/cli/cache_spec.rb
index b1515801eb5..247a14f9e27 100644
--- a/spec/lib/mastodon/cli/cache_spec.rb
+++ b/spec/lib/mastodon/cli/cache_spec.rb
@@ -64,8 +64,7 @@ describe Mastodon::CLI::Cache do
 
       it 'Exits with an error message' do
         expect { subject }
-          .to output_results('Unknown')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /Unknown/)
       end
     end
   end
diff --git a/spec/lib/mastodon/cli/email_domain_blocks_spec.rb b/spec/lib/mastodon/cli/email_domain_blocks_spec.rb
index 13deb05b6cf..55e3da0bb89 100644
--- a/spec/lib/mastodon/cli/email_domain_blocks_spec.rb
+++ b/spec/lib/mastodon/cli/email_domain_blocks_spec.rb
@@ -35,8 +35,7 @@ describe Mastodon::CLI::EmailDomainBlocks do
     context 'without any options' do
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('No domain(s) given')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No domain(s) given')
       end
     end
 
@@ -72,8 +71,7 @@ describe Mastodon::CLI::EmailDomainBlocks do
     context 'without any options' do
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('No domain(s) given')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No domain(s) given')
       end
     end
 
diff --git a/spec/lib/mastodon/cli/feeds_spec.rb b/spec/lib/mastodon/cli/feeds_spec.rb
index 19979805270..420cb3d5872 100644
--- a/spec/lib/mastodon/cli/feeds_spec.rb
+++ b/spec/lib/mastodon/cli/feeds_spec.rb
@@ -42,8 +42,7 @@ describe Mastodon::CLI::Feeds do
 
       it 'displays an error and exits' do
         expect { subject }
-          .to output_results('No such account')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No such account')
       end
     end
   end
diff --git a/spec/lib/mastodon/cli/ip_blocks_spec.rb b/spec/lib/mastodon/cli/ip_blocks_spec.rb
index 82be10813ed..d44b1b9fe44 100644
--- a/spec/lib/mastodon/cli/ip_blocks_spec.rb
+++ b/spec/lib/mastodon/cli/ip_blocks_spec.rb
@@ -144,8 +144,7 @@ describe Mastodon::CLI::IpBlocks do
 
       it 'exits with an error message' do
         expect { subject }
-          .to output_results('No IP(s) given')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No IP(s) given')
       end
     end
   end
@@ -235,8 +234,7 @@ describe Mastodon::CLI::IpBlocks do
     context 'when no IP address is provided' do
       it 'exits with an error message' do
         expect { subject }
-          .to output_results('No IP(s) given')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'No IP(s) given')
       end
     end
   end
diff --git a/spec/lib/mastodon/cli/main_spec.rb b/spec/lib/mastodon/cli/main_spec.rb
index 081cd2dd47d..99d770a81dd 100644
--- a/spec/lib/mastodon/cli/main_spec.rb
+++ b/spec/lib/mastodon/cli/main_spec.rb
@@ -104,9 +104,9 @@ describe Mastodon::CLI::Main do
           answer_hostname_incorrectly
         end
 
-        it 'exits silently' do
+        it 'exits with mismatch error message' do
           expect { subject }
-            .to raise_error(SystemExit)
+            .to raise_error(Thor::Error, /Domains do not match/)
         end
       end
 
@@ -119,7 +119,7 @@ describe Mastodon::CLI::Main do
         it 'passes first step but stops before instructions' do
           expect { subject }
             .to output_results('operation WILL NOT')
-            .and raise_error(SystemExit)
+            .and raise_error(Thor::Error, /Self-destruct will not begin/)
         end
       end
 
diff --git a/spec/lib/mastodon/cli/maintenance_spec.rb b/spec/lib/mastodon/cli/maintenance_spec.rb
index ca492bbf69c..cde25d39eda 100644
--- a/spec/lib/mastodon/cli/maintenance_spec.rb
+++ b/spec/lib/mastodon/cli/maintenance_spec.rb
@@ -22,8 +22,7 @@ describe Mastodon::CLI::Maintenance do
 
       it 'Exits with error message' do
         expect { subject }
-          .to output_results('is too old')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /is too old/)
       end
     end
 
@@ -36,7 +35,7 @@ describe Mastodon::CLI::Maintenance do
       it 'Exits with error message' do
         expect { subject }
           .to output_results('more recent')
-          .and raise_error(SystemExit)
+          .and raise_error(Thor::Error, /more recent/)
       end
     end
 
@@ -48,8 +47,7 @@ describe Mastodon::CLI::Maintenance do
 
       it 'Exits with error message' do
         expect { subject }
-          .to output_results('Sidekiq is running')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /Sidekiq is running/)
       end
     end
 
diff --git a/spec/lib/mastodon/cli/media_spec.rb b/spec/lib/mastodon/cli/media_spec.rb
index 10005107aa5..ecc7101b6cf 100644
--- a/spec/lib/mastodon/cli/media_spec.rb
+++ b/spec/lib/mastodon/cli/media_spec.rb
@@ -20,8 +20,7 @@ describe Mastodon::CLI::Media do
 
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('--prune-profiles and --remove-headers should not be specified simultaneously')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, '--prune-profiles and --remove-headers should not be specified simultaneously')
       end
     end
 
@@ -30,8 +29,7 @@ describe Mastodon::CLI::Media do
 
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('--include-follows can only be used with --prune-profiles or --remove-headers')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, '--include-follows can only be used with --prune-profiles or --remove-headers')
       end
     end
 
@@ -98,8 +96,7 @@ describe Mastodon::CLI::Media do
 
       it 'warns about url and exits' do
         expect { subject }
-          .to output_results('Not a media URL')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, 'Not a media URL')
       end
     end
 
@@ -121,8 +118,7 @@ describe Mastodon::CLI::Media do
     context 'without any options' do
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('Specify the source')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /Specify the source/)
       end
     end
 
@@ -147,8 +143,7 @@ describe Mastodon::CLI::Media do
 
         it 'warns about usage and exits' do
           expect { subject }
-            .to output_results('No such account')
-            .and raise_error(SystemExit)
+            .to raise_error(Thor::Error, 'No such account')
         end
       end
 
@@ -221,8 +216,7 @@ describe Mastodon::CLI::Media do
 
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('azure storage driver is not supported')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /azure storage driver is not supported/)
       end
     end
 
@@ -233,8 +227,7 @@ describe Mastodon::CLI::Media do
 
       it 'warns about usage and exits' do
         expect { subject }
-          .to output_results('fog storage driver is not supported')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /fog storage driver is not supported/)
       end
     end
 
diff --git a/spec/lib/mastodon/cli/search_spec.rb b/spec/lib/mastodon/cli/search_spec.rb
index cb0c80c11db..8cce2c6ee22 100644
--- a/spec/lib/mastodon/cli/search_spec.rb
+++ b/spec/lib/mastodon/cli/search_spec.rb
@@ -20,8 +20,7 @@ describe Mastodon::CLI::Search do
 
       it 'Exits with error message' do
         expect { subject }
-          .to output_results('this concurrency setting')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /this concurrency setting/)
       end
     end
 
@@ -30,8 +29,7 @@ describe Mastodon::CLI::Search do
 
       it 'Exits with error message' do
         expect { subject }
-          .to output_results('this batch_size setting')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /this batch_size setting/)
       end
     end
 
diff --git a/spec/lib/mastodon/cli/statuses_spec.rb b/spec/lib/mastodon/cli/statuses_spec.rb
index 63d494bbb65..161b7c02bbf 100644
--- a/spec/lib/mastodon/cli/statuses_spec.rb
+++ b/spec/lib/mastodon/cli/statuses_spec.rb
@@ -20,8 +20,7 @@ describe Mastodon::CLI::Statuses do
 
       it 'exits with error message' do
         expect { subject }
-          .to output_results('Cannot run')
-          .and raise_error(SystemExit)
+          .to raise_error(Thor::Error, /Cannot run/)
       end
     end