diff --git a/Library/Homebrew/cask/artifact/prefpane.rb b/Library/Homebrew/cask/artifact/prefpane.rb
index 8dc2df4559..a2a1057b34 100644
--- a/Library/Homebrew/cask/artifact/prefpane.rb
+++ b/Library/Homebrew/cask/artifact/prefpane.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 require "cask/artifact/moved"
diff --git a/Library/Homebrew/cask/artifact/suite.rb b/Library/Homebrew/cask/artifact/suite.rb
index 043b4f0b9e..5eb8462640 100644
--- a/Library/Homebrew/cask/artifact/suite.rb
+++ b/Library/Homebrew/cask/artifact/suite.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 require "cask/artifact/moved"
diff --git a/Library/Homebrew/cask/cmd/abstract_internal_command.rb b/Library/Homebrew/cask/cmd/abstract_internal_command.rb
index a0a45e8b1b..0fb1e2152c 100644
--- a/Library/Homebrew/cask/cmd/abstract_internal_command.rb
+++ b/Library/Homebrew/cask/cmd/abstract_internal_command.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 module Cask
diff --git a/Library/Homebrew/cask/cmd/cat.rb b/Library/Homebrew/cask/cmd/cat.rb
index d5d2afdc6a..bb741992ea 100644
--- a/Library/Homebrew/cask/cmd/cat.rb
+++ b/Library/Homebrew/cask/cmd/cat.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 module Cask
diff --git a/Library/Homebrew/cask/cmd/internal_help.rb b/Library/Homebrew/cask/cmd/internal_help.rb
index 3f6476e29a..98f1011d4c 100644
--- a/Library/Homebrew/cask/cmd/internal_help.rb
+++ b/Library/Homebrew/cask/cmd/internal_help.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 module Cask
diff --git a/Library/Homebrew/cmd/--cellar.rb b/Library/Homebrew/cmd/--cellar.rb
index 2af781142c..a4be852c20 100644
--- a/Library/Homebrew/cmd/--cellar.rb
+++ b/Library/Homebrew/cmd/--cellar.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/cmd/--prefix.rb b/Library/Homebrew/cmd/--prefix.rb
index 42410ab30a..c21b187495 100644
--- a/Library/Homebrew/cmd/--prefix.rb
+++ b/Library/Homebrew/cmd/--prefix.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/cmd/--repository.rb b/Library/Homebrew/cmd/--repository.rb
index c27c4589fd..3f68fa9c4c 100644
--- a/Library/Homebrew/cmd/--repository.rb
+++ b/Library/Homebrew/cmd/--repository.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/cmd/--version.rb b/Library/Homebrew/cmd/--version.rb
index ff038f7096..de305d3579 100644
--- a/Library/Homebrew/cmd/--version.rb
+++ b/Library/Homebrew/cmd/--version.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/cmd/analytics.rb b/Library/Homebrew/cmd/analytics.rb
index 0efdf6afe1..aa64043274 100644
--- a/Library/Homebrew/cmd/analytics.rb
+++ b/Library/Homebrew/cmd/analytics.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/cmd/autoremove.rb b/Library/Homebrew/cmd/autoremove.rb
index 21c211cfea..e65d3a59b0 100644
--- a/Library/Homebrew/cmd/autoremove.rb
+++ b/Library/Homebrew/cmd/autoremove.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/cleanup.rb b/Library/Homebrew/cmd/cleanup.rb
index 0c7ac6df81..786c28eee3 100644
--- a/Library/Homebrew/cmd/cleanup.rb
+++ b/Library/Homebrew/cmd/cleanup.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cleanup"
diff --git a/Library/Homebrew/cmd/config.rb b/Library/Homebrew/cmd/config.rb
index 970af3093a..3153cdd54b 100644
--- a/Library/Homebrew/cmd/config.rb
+++ b/Library/Homebrew/cmd/config.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "system_config"
diff --git a/Library/Homebrew/cmd/gist-logs.rb b/Library/Homebrew/cmd/gist-logs.rb
index a42d2457f9..d264c86151 100644
--- a/Library/Homebrew/cmd/gist-logs.rb
+++ b/Library/Homebrew/cmd/gist-logs.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/leaves.rb b/Library/Homebrew/cmd/leaves.rb
index f4c2c471a7..11563f2e30 100644
--- a/Library/Homebrew/cmd/leaves.rb
+++ b/Library/Homebrew/cmd/leaves.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/link.rb b/Library/Homebrew/cmd/link.rb
index 98a265d610..b8a3204712 100644
--- a/Library/Homebrew/cmd/link.rb
+++ b/Library/Homebrew/cmd/link.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "ostruct"
diff --git a/Library/Homebrew/cmd/migrate.rb b/Library/Homebrew/cmd/migrate.rb
index b5bf51a008..db71a53dfb 100644
--- a/Library/Homebrew/cmd/migrate.rb
+++ b/Library/Homebrew/cmd/migrate.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "migrator"
diff --git a/Library/Homebrew/cmd/missing.rb b/Library/Homebrew/cmd/missing.rb
index 4ab86a49fc..4eabe779ee 100644
--- a/Library/Homebrew/cmd/missing.rb
+++ b/Library/Homebrew/cmd/missing.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/pin.rb b/Library/Homebrew/cmd/pin.rb
index b777ac3b5f..ce0b48ffa7 100644
--- a/Library/Homebrew/cmd/pin.rb
+++ b/Library/Homebrew/cmd/pin.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/postinstall.rb b/Library/Homebrew/cmd/postinstall.rb
index ce7113833d..de70cae3d5 100644
--- a/Library/Homebrew/cmd/postinstall.rb
+++ b/Library/Homebrew/cmd/postinstall.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "sandbox"
diff --git a/Library/Homebrew/cmd/readall.rb b/Library/Homebrew/cmd/readall.rb
index 7a2361036c..353733bc9d 100644
--- a/Library/Homebrew/cmd/readall.rb
+++ b/Library/Homebrew/cmd/readall.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "readall"
diff --git a/Library/Homebrew/cmd/switch.rb b/Library/Homebrew/cmd/switch.rb
index 3f3e4baaf3..a25cccce48 100644
--- a/Library/Homebrew/cmd/switch.rb
+++ b/Library/Homebrew/cmd/switch.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/tap.rb b/Library/Homebrew/cmd/tap.rb
index 86e7a0fc1b..8dab836970 100644
--- a/Library/Homebrew/cmd/tap.rb
+++ b/Library/Homebrew/cmd/tap.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/cmd/unlink.rb b/Library/Homebrew/cmd/unlink.rb
index 1036b8eaf9..43a9a8dca1 100644
--- a/Library/Homebrew/cmd/unlink.rb
+++ b/Library/Homebrew/cmd/unlink.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "ostruct"
diff --git a/Library/Homebrew/cmd/unpin.rb b/Library/Homebrew/cmd/unpin.rb
index 1f650adae1..0c1b7fcbcf 100644
--- a/Library/Homebrew/cmd/unpin.rb
+++ b/Library/Homebrew/cmd/unpin.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/cmd/untap.rb b/Library/Homebrew/cmd/untap.rb
index d3e70e7e5e..b83667fed6 100644
--- a/Library/Homebrew/cmd/untap.rb
+++ b/Library/Homebrew/cmd/untap.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/compat/language/haskell.rb b/Library/Homebrew/compat/language/haskell.rb
index 00f6466807..ccb7901681 100644
--- a/Library/Homebrew/compat/language/haskell.rb
+++ b/Library/Homebrew/compat/language/haskell.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Language
diff --git a/Library/Homebrew/dev-cmd/bump-revision.rb b/Library/Homebrew/dev-cmd/bump-revision.rb
index 745fef7717..18d2a94379 100644
--- a/Library/Homebrew/dev-cmd/bump-revision.rb
+++ b/Library/Homebrew/dev-cmd/bump-revision.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/dev-cmd/bump.rb b/Library/Homebrew/dev-cmd/bump.rb
index 00f51e8870..adf8878735 100644
--- a/Library/Homebrew/dev-cmd/bump.rb
+++ b/Library/Homebrew/dev-cmd/bump.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/dev-cmd/command.rb b/Library/Homebrew/dev-cmd/command.rb
index 9beb128138..eb946cf636 100644
--- a/Library/Homebrew/dev-cmd/command.rb
+++ b/Library/Homebrew/dev-cmd/command.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "commands"
diff --git a/Library/Homebrew/dev-cmd/dispatch-build-bottle.rb b/Library/Homebrew/dev-cmd/dispatch-build-bottle.rb
index fbb867e8ae..21d5af7617 100644
--- a/Library/Homebrew/dev-cmd/dispatch-build-bottle.rb
+++ b/Library/Homebrew/dev-cmd/dispatch-build-bottle.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/dev-cmd/diy.rb b/Library/Homebrew/dev-cmd/diy.rb
index aba0a000ff..8a11fa2d76 100644
--- a/Library/Homebrew/dev-cmd/diy.rb
+++ b/Library/Homebrew/dev-cmd/diy.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/dev-cmd/edit.rb b/Library/Homebrew/dev-cmd/edit.rb
index dc4a814e5a..e06b67eaad 100644
--- a/Library/Homebrew/dev-cmd/edit.rb
+++ b/Library/Homebrew/dev-cmd/edit.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/dev-cmd/formula.rb b/Library/Homebrew/dev-cmd/formula.rb
index cee7263e9a..17bfd4a806 100644
--- a/Library/Homebrew/dev-cmd/formula.rb
+++ b/Library/Homebrew/dev-cmd/formula.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/dev-cmd/install-bundler-gems.rb b/Library/Homebrew/dev-cmd/install-bundler-gems.rb
index ce80576cb1..d1c3bd88d6 100644
--- a/Library/Homebrew/dev-cmd/install-bundler-gems.rb
+++ b/Library/Homebrew/dev-cmd/install-bundler-gems.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "formula"
diff --git a/Library/Homebrew/dev-cmd/linkage.rb b/Library/Homebrew/dev-cmd/linkage.rb
index 4f161f8039..63ae8066a1 100644
--- a/Library/Homebrew/dev-cmd/linkage.rb
+++ b/Library/Homebrew/dev-cmd/linkage.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cache_store"
diff --git a/Library/Homebrew/dev-cmd/livecheck.rb b/Library/Homebrew/dev-cmd/livecheck.rb
index 2e6ab72334..26af2ffb88 100644
--- a/Library/Homebrew/dev-cmd/livecheck.rb
+++ b/Library/Homebrew/dev-cmd/livecheck.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/dev-cmd/mirror.rb b/Library/Homebrew/dev-cmd/mirror.rb
index 29c238f6a9..ec6f44d8fc 100644
--- a/Library/Homebrew/dev-cmd/mirror.rb
+++ b/Library/Homebrew/dev-cmd/mirror.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "bintray"
diff --git a/Library/Homebrew/dev-cmd/release-notes.rb b/Library/Homebrew/dev-cmd/release-notes.rb
index 3e7286cdc4..26cbe6e5e1 100644
--- a/Library/Homebrew/dev-cmd/release-notes.rb
+++ b/Library/Homebrew/dev-cmd/release-notes.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/dev-cmd/style.rb b/Library/Homebrew/dev-cmd/style.rb
index 611ab05ce0..c0112ef519 100644
--- a/Library/Homebrew/dev-cmd/style.rb
+++ b/Library/Homebrew/dev-cmd/style.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "json"
diff --git a/Library/Homebrew/dev-cmd/typecheck.rb b/Library/Homebrew/dev-cmd/typecheck.rb
index 454715b098..b544af5c10 100644
--- a/Library/Homebrew/dev-cmd/typecheck.rb
+++ b/Library/Homebrew/dev-cmd/typecheck.rb
@@ -22,6 +22,9 @@ module Homebrew
              description: "Silence all non-critical errors."
       switch "--update",
              description: "Update RBI files."
+      switch "--suggest-typed",
+             description: "Try upgrading `typed` sigils.",
+             depends_on:  "--update"
       switch "--fail-if-not-changed",
              description: "Return a failing status code if all gems are up to date " \
                           "and gem definitions do not need a tapioca update."
@@ -38,6 +41,7 @@ module Homebrew
     end
   end
 
+  sig { void }
   def typecheck
     args = typecheck_args.parse
 
@@ -50,12 +54,44 @@ module Homebrew
         system "bundle", "exec", "srb", "rbi", "hidden-definitions"
         system "bundle", "exec", "srb", "rbi", "todo"
 
+        if args.suggest_typed?
+          result = system_command(
+            "bundle",
+            args:         ["exec", "--", "srb", "tc", "--suggest-typed", "--typed=strict", "--error-white-list=7022"],
+            print_stderr: false,
+          )
+
+          allowed_changes = {
+            "false" => ["true", "strict"],
+            "true"  => ["strict"],
+          }
+
+          # Workaround for `srb tc rbi suggest-typed`, which currently fails get to a converging state.
+          result.stderr.scan(/^(.*\.rb):\d+:\s+You could add `#\s*typed:\s*(.*?)`/).each do |path, new_level|
+            path = Pathname(path)
+
+            next unless path.file?
+
+            contents = path.read
+
+            next unless (match = contents.match(/\A\s*#\s*typed:\s*([^\s]+)/))
+
+            existing_level = match[1]
+
+            next unless allowed_changes.fetch(existing_level, []).include?(new_level)
+
+            puts "#{path}: #{existing_level} -> #{new_level}"
+            path.atomic_write contents.sub(/\A(\s*#\s*typed:\s*)(?:[^\s]+)/, "\\1#{new_level}")
+          end
+        end
+
         Homebrew.failed = system("git", "diff", "--stat", "--exit-code") if args.fail_if_not_changed?
 
         return
       end
 
       srb_exec = %w[bundle exec srb tc]
+      srb_exec << "--error-black-list" << "5061"
       srb_exec << "--quiet" if args.quiet?
       srb_exec << "--autocorrect" if args.fix?
       srb_exec += ["--ignore", args.ignore] if args.ignore.present?
diff --git a/Library/Homebrew/dev-cmd/update-license-data.rb b/Library/Homebrew/dev-cmd/update-license-data.rb
index c41c6ace7f..ef51979c7e 100644
--- a/Library/Homebrew/dev-cmd/update-license-data.rb
+++ b/Library/Homebrew/dev-cmd/update-license-data.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/dev-cmd/update-python-resources.rb b/Library/Homebrew/dev-cmd/update-python-resources.rb
index 936dad5aba..a66710f516 100644
--- a/Library/Homebrew/dev-cmd/update-python-resources.rb
+++ b/Library/Homebrew/dev-cmd/update-python-resources.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/Library/Homebrew/extend/os/linux/requirements/xcode_requirement.rb b/Library/Homebrew/extend/os/linux/requirements/xcode_requirement.rb
index caa020aba4..8ebc4ecd72 100644
--- a/Library/Homebrew/extend/os/linux/requirements/xcode_requirement.rb
+++ b/Library/Homebrew/extend/os/linux/requirements/xcode_requirement.rb
@@ -1,9 +1,12 @@
-# typed: false
+# typed: strict
 # frozen_string_literal: true
 
 require "requirement"
 
 class XcodeRequirement < Requirement
+  extend T::Sig
+
+  sig { returns(T::Boolean) }
   def xcode_installed_version
     true
   end
diff --git a/Library/Homebrew/extend/os/mac/extend/ENV/shared.rb b/Library/Homebrew/extend/os/mac/extend/ENV/shared.rb
index d882025a2b..4b8c366ef7 100644
--- a/Library/Homebrew/extend/os/mac/extend/ENV/shared.rb
+++ b/Library/Homebrew/extend/os/mac/extend/ENV/shared.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 module SharedEnvExtension
diff --git a/Library/Homebrew/extend/os/requirements/xcode_requirement.rb b/Library/Homebrew/extend/os/requirements/xcode_requirement.rb
index d8895dbfac..e14c754593 100644
--- a/Library/Homebrew/extend/os/requirements/xcode_requirement.rb
+++ b/Library/Homebrew/extend/os/requirements/xcode_requirement.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: strict
 # frozen_string_literal: true
 
 require "extend/os/linux/requirements/xcode_requirement" if OS.linux?
diff --git a/Library/Homebrew/formula_text_auditor.rb b/Library/Homebrew/formula_text_auditor.rb
index 02c6069d35..b4bcc52453 100644
--- a/Library/Homebrew/formula_text_auditor.rb
+++ b/Library/Homebrew/formula_text_auditor.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/language/node.rb b/Library/Homebrew/language/node.rb
index 1e5e48f7b5..d59d433295 100644
--- a/Library/Homebrew/language/node.rb
+++ b/Library/Homebrew/language/node.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Language
diff --git a/Library/Homebrew/requirement.rb b/Library/Homebrew/requirement.rb
index 11a87bc433..e609aa77d4 100644
--- a/Library/Homebrew/requirement.rb
+++ b/Library/Homebrew/requirement.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "dependable"
diff --git a/Library/Homebrew/requirements/linux_requirement.rb b/Library/Homebrew/requirements/linux_requirement.rb
index 410c39bcc4..36b70585ac 100644
--- a/Library/Homebrew/requirements/linux_requirement.rb
+++ b/Library/Homebrew/requirements/linux_requirement.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 # A requirement on Linux.
diff --git a/Library/Homebrew/requirements/xcode_requirement.rb b/Library/Homebrew/requirements/xcode_requirement.rb
index 775d62fc56..ccc8412b84 100644
--- a/Library/Homebrew/requirements/xcode_requirement.rb
+++ b/Library/Homebrew/requirements/xcode_requirement.rb
@@ -20,6 +20,7 @@ class XcodeRequirement < Requirement
     super(tags)
   end
 
+  sig { returns(T::Boolean) }
   def xcode_installed_version
     return false unless MacOS::Xcode.installed?
     return true unless @version
diff --git a/Library/Homebrew/resource.rb b/Library/Homebrew/resource.rb
index d17bc7be56..ab19c7b39b 100644
--- a/Library/Homebrew/resource.rb
+++ b/Library/Homebrew/resource.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "download_strategy"
diff --git a/Library/Homebrew/resource_auditor.rb b/Library/Homebrew/resource_auditor.rb
index f386eb511a..5e0e941a22 100644
--- a/Library/Homebrew/resource_auditor.rb
+++ b/Library/Homebrew/resource_auditor.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Homebrew
diff --git a/Library/Homebrew/rubocops/cask/extend/string.rb b/Library/Homebrew/rubocops/cask/extend/string.rb
index f4e4ee3be0..3f71c87c2f 100644
--- a/Library/Homebrew/rubocops/cask/extend/string.rb
+++ b/Library/Homebrew/rubocops/cask/extend/string.rb
@@ -1,4 +1,4 @@
-# typed: true
+# typed: strict
 # frozen_string_literal: true
 
 # Utility method extensions for String.
diff --git a/Library/Homebrew/sorbet/config b/Library/Homebrew/sorbet/config
index 91f8209a58..024ba458ec 100644
--- a/Library/Homebrew/sorbet/config
+++ b/Library/Homebrew/sorbet/config
@@ -9,6 +9,3 @@
 
 --dsl-plugins
 sorbet/triggers.yml
-
---error-black-list
-5061
diff --git a/Library/Homebrew/system_command.rb b/Library/Homebrew/system_command.rb
index 33ce5069bc..d00d934895 100644
--- a/Library/Homebrew/system_command.rb
+++ b/Library/Homebrew/system_command.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "open3"
diff --git a/Library/Homebrew/test/support/helper/cmd/brew-verify-formula-undefined.rb b/Library/Homebrew/test/support/helper/cmd/brew-verify-formula-undefined.rb
index eaa659e8ae..3b08180cd1 100755
--- a/Library/Homebrew/test/support/helper/cmd/brew-verify-formula-undefined.rb
+++ b/Library/Homebrew/test/support/helper/cmd/brew-verify-formula-undefined.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: strict
 # frozen_string_literal: true
 
 require "cli/parser"
diff --git a/docs/Manpage.md b/docs/Manpage.md
index 5af239c2b7..f8941af446 100644
--- a/docs/Manpage.md
+++ b/docs/Manpage.md
@@ -1269,6 +1269,8 @@ Check for typechecking errors using Sorbet.
   Silence all non-critical errors.
 * `--update`:
   Update RBI files.
+* `--suggest-typed`:
+  Try upgrading `typed` sigils.
 * `--fail-if-not-changed`:
   Return a failing status code if all gems are up to date and gem definitions do not need a tapioca update.
 * `--dir`:
diff --git a/manpages/brew.1 b/manpages/brew.1
index 5cdaf4721b..3bc17a0e5d 100644
--- a/manpages/brew.1
+++ b/manpages/brew.1
@@ -1753,6 +1753,10 @@ Silence all non\-critical errors\.
 Update RBI files\.
 .
 .TP
+\fB\-\-suggest\-typed\fR
+Try upgrading \fBtyped\fR sigils\.
+.
+.TP
 \fB\-\-fail\-if\-not\-changed\fR
 Return a failing status code if all gems are up to date and gem definitions do not need a tapioca update\.
 .