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/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/docs/Manpage.md b/docs/Manpage.md
index 3d833eabed..b94b19b529 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 d9777aad0d..ea3a8681f7 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\.
 .