diff --git a/lib/spoom/cli/srb/bump.rb b/lib/spoom/cli/srb/bump.rb
index dfa369a8..0e3b6c60 100644
--- a/lib/spoom/cli/srb/bump.rb
+++ b/lib/spoom/cli/srb/bump.rb
@@ -3,6 +3,8 @@
 
 require "find"
 require "open3"
+require "securerandom"
+require "yaml"
 
 module Spoom
   module Cli
@@ -72,6 +74,11 @@ def bump(directory = ".")
             exit(1)
           end
 
+          unless context.sorbet_config.typed_overrides.empty?
+            say_error("Cannot run `spoom bump` on a project that already uses Sorbet's `--typed-override` option")
+            exit(1)
+          end
+
           say("Checking files...")
 
           files_to_bump = context.srb_files_with_strictness(from, include_rbis: false)
@@ -90,18 +97,18 @@ def bump(directory = ".")
             exit(0)
           end
 
-          Sorbet::Sigils.change_sigil_in_files(files_to_bump, to)
-
           if force
+            Sorbet::Sigils.change_sigil_in_files(files_to_bump, to) unless dry
             print_changes(files_to_bump, command: cmd, from: from, to: to, dry: dry, path: exec_path)
-            undo_changes(files_to_bump, from) if dry
             exit(files_to_bump.empty?)
           end
 
           error_url_base = Spoom::Sorbet::Errors::DEFAULT_ERROR_URL_BASE
+          typed_override_file = write_typed_override_file(context, files_to_bump, to)
           result = begin
             T.unsafe(context).srb_tc(
               *options[:sorbet_options].split(" "),
+              "--typed-override=#{typed_override_file}",
               "--error-url-base=#{error_url_base}",
               capture_err: true,
               sorbet_bin: options[:sorbet],
@@ -114,7 +121,6 @@ def bump(directory = ".")
               It means one of the file bumped to `typed: #{to}` made Sorbet crash.
               Run `spoom bump -f` locally followed by `bundle exec srb tc` to investigate the problem.
             ERR
-            undo_changes(files_to_bump, from)
             exit(error.result.exit_code)
           rescue Spoom::Sorbet::Error::Killed => error
             say_error(<<~ERR, status: nil)
@@ -123,13 +129,14 @@ def bump(directory = ".")
               It means Sorbet was killed while executing. Changes to files have not been applied.
               Re-run `spoom bump` to try again.
             ERR
-            undo_changes(files_to_bump, from)
             exit(error.result.exit_code)
+          ensure
+            context.remove!(typed_override_file)
           end
 
           if result.status
+            Sorbet::Sigils.change_sigil_in_files(files_to_bump, to) unless dry
             print_changes(files_to_bump, command: cmd, from: from, to: to, dry: dry, path: exec_path)
-            undo_changes(files_to_bump, from) if dry
             exit(files_to_bump.empty?)
           end
 
@@ -137,7 +144,6 @@ def bump(directory = ".")
             # Sorbet will return exit code 100 if there are type checking errors.
             # If Sorbet returned something else, it means it didn't terminate normally.
             say_error(result.err, status: nil, nl: false)
-            undo_changes(files_to_bump, from)
             exit(1)
           end
 
@@ -156,13 +162,11 @@ def bump(directory = ".")
             path
           end.compact.uniq
 
-          undo_changes(files_with_errors, from)
-
           say("Found #{errors.length} type checking error#{"s" if errors.length > 1}") if options[:count_errors]
 
           files_changed = files_to_bump - files_with_errors
+          Sorbet::Sigils.change_sigil_in_files(files_changed, to) unless dry
           print_changes(files_changed, command: cmd, from: from, to: to, dry: dry, path: exec_path)
-          undo_changes(files_to_bump, from) if dry
           exit(files_changed.empty?)
         end
 
@@ -189,8 +193,15 @@ def print_changes(files, command:, from: "false", to: "true", dry: false, path:
             end
           end
 
-          def undo_changes(files, from_strictness)
-            Sorbet::Sigils.change_sigil_in_files(files, from_strictness)
+          #: (Spoom::Context context, Array[String] files, String strictness) -> String
+          def write_typed_override_file(context, files, strictness)
+            path = ".spoom-typed-override-#{Process.pid}-#{SecureRandom.hex(8)}.yaml"
+            relative_paths = files.map do |file|
+              relative_path = file.delete_prefix("#{context.absolute_path}/")
+              "./#{relative_path}"
+            end
+            context.write!(path, YAML.dump({ strictness => relative_paths }))
+            path
           end
         end
       end
diff --git a/lib/spoom/sorbet/config.rb b/lib/spoom/sorbet/config.rb
index 14b15ce5..010a71e2 100644
--- a/lib/spoom/sorbet/config.rb
+++ b/lib/spoom/sorbet/config.rb
@@ -27,7 +27,7 @@ class Config
       DEFAULT_ALLOWED_EXTENSIONS = [".rb", ".rbi"].freeze #: Array[String]
 
       #: Array[String]
-      attr_accessor :paths, :ignore, :allowed_extensions
+      attr_accessor :paths, :ignore, :allowed_extensions, :typed_overrides
 
       #: bool
       attr_accessor :no_stdlib
@@ -37,6 +37,7 @@ def initialize
         @paths = [] #: Array[String]
         @ignore = [] #: Array[String]
         @allowed_extensions = [] #: Array[String]
+        @typed_overrides = [] #: Array[String]
         @no_stdlib = false #: bool
       end
 
@@ -46,6 +47,7 @@ def initialize_copy(source)
         @paths = @paths.dup
         @ignore = @ignore.dup
         @allowed_extensions = @allowed_extensions.dup
+        @typed_overrides = @typed_overrides.dup
       end
 
       # Returns self as a string of options that can be passed to Sorbet
@@ -66,6 +68,7 @@ def options_string
         opts.concat(paths.map { |p| "'#{p}'" })
         opts.concat(ignore.map { |p| "--ignore '#{p}'" })
         opts.concat(allowed_extensions.map { |ext| "--allowed-extension '#{ext}'" })
+        opts.concat(typed_overrides.map { |path| "--typed-override '#{path}'" })
         opts << "--no-stdlib" if @no_stdlib
         opts.join(" ")
       end
@@ -95,6 +98,12 @@ def parse_string(sorbet_config)
             when /^--ignore=/
               config.ignore << parse_option(line)
               next
+            when /^--typed-override$/
+              state = :typed_override
+              next
+            when /^--typed-override=/
+              config.typed_overrides << parse_option(line)
+              next
             when /^--file$/
               next
             when /^--file=/
@@ -124,6 +133,8 @@ def parse_string(sorbet_config)
                 config.ignore << line
               when :extension
                 config.allowed_extensions << line
+              when :typed_override
+                config.typed_overrides << line
               when :skip
                 # nothing
               else
diff --git a/rbi/spoom.rbi b/rbi/spoom.rbi
index 254e5f03..7c3787f4 100644
--- a/rbi/spoom.rbi
+++ b/rbi/spoom.rbi
@@ -128,7 +128,9 @@ class Spoom::Cli::Srb::Bump < ::Thor
 
   def help(command = T.unsafe(nil), subcommand = T.unsafe(nil)); end
   def print_changes(files, command:, from: T.unsafe(nil), to: T.unsafe(nil), dry: T.unsafe(nil), path: T.unsafe(nil)); end
-  def undo_changes(files, from_strictness); end
+
+  sig { params(context: ::Spoom::Context, files: T::Array[::String], strictness: ::String).returns(::String) }
+  def write_typed_override_file(context, files, strictness); end
 end
 
 class Spoom::Cli::Srb::Coverage < ::Thor
@@ -2661,6 +2663,8 @@ class Spoom::Sorbet::Config
   def paths; end
 
   def paths=(_arg0); end
+  def typed_overrides; end
+  def typed_overrides=(_arg0); end
 
   private
 
diff --git a/test/spoom/cli/srb/bump_test.rb b/test/spoom/cli/srb/bump_test.rb
index ee548599..5035bb56 100644
--- a/test/spoom/cli/srb/bump_test.rb
+++ b/test/spoom/cli/srb/bump_test.rb
@@ -11,6 +11,12 @@ def setup
           @project.bundle_install!
         end
 
+        def teardown
+          assert_empty(Dir.glob("#{@project.absolute_path}/.spoom-typed-override-*"))
+        ensure
+          super
+        end
+
         def test_bump_outside_sorbet_dir
           @project.remove!("sorbet/config")
           result = @project.spoom("srb bump --no-color")
@@ -54,6 +60,30 @@ class A; end
           assert_equal("false", @project.read_file_strictness("file2.rb"))
         end
 
+        def test_bump_errors_if_sorbet_config_has_typed_override
+          @project.write_sorbet_config!(<<~CONFIG)
+            .
+            --typed-override=typed-override.yaml
+          CONFIG
+          @project.write!("typed-override.yaml", <<~YAML)
+            true:
+              - ./file.rb
+          YAML
+          @project.write!("file.rb", <<~RB)
+            # typed: false
+            class A; end
+          RB
+
+          result = @project.spoom("srb bump --no-color")
+          assert_empty(result.out)
+          assert_equal(<<~ERR, result.err)
+            Error: Cannot run `spoom bump` on a project that already uses Sorbet's `--typed-override` option
+          ERR
+          refute(result.status)
+
+          assert_equal("false", @project.read_file_strictness("file.rb"))
+        end
+
         def test_bump_doesnt_change_sigils_outside_directory
           @project.write!("lib/a/file.rb", "# typed: false")
           @project.write!("lib/b/file.rb", "# typed: false")
diff --git a/test/spoom/sorbet/config_test.rb b/test/spoom/sorbet/config_test.rb
index 8aac162c..717fe213 100644
--- a/test/spoom/sorbet/config_test.rb
+++ b/test/spoom/sorbet/config_test.rb
@@ -71,6 +71,19 @@ def test_parses_a_config_string_with_ignore_options
         assert_empty(config.allowed_extensions)
       end
 
+      def test_parses_a_config_string_with_typed_override_options
+        config = Spoom::Sorbet::Config.parse_string(<<~CONFIG)
+          a
+          --typed-override=b.yaml
+          c
+          --typed-override
+          d.yaml
+          e
+        CONFIG
+        assert_equal(["a", "c", "e"], config.paths)
+        assert_equal(["b.yaml", "d.yaml"], config.typed_overrides)
+      end
+
       def test_parses_a_config_string_with_other_options
         config = Spoom::Sorbet::Config.parse_string(<<~CONFIG)
           a
@@ -241,12 +254,14 @@ def test_options_string_with_options
           --ignore=.git/
           --ignore=vendor/
           --allowed-extension=.rb
+          --typed-override=typed-override.yaml
           --no-stdlib
         CONFIG
         expected = "'.' " \
           "--ignore '.git/' " \
           "--ignore 'vendor/' " \
           "--allowed-extension '.rb' " \
+          "--typed-override 'typed-override.yaml' " \
           "--no-stdlib"
         assert_equal(expected, config.options_string)
       end