diff --git a/Library/Homebrew/PATH.rb b/Library/Homebrew/PATH.rb
index 46fd38bb3f..099613ac95 100644
--- a/Library/Homebrew/PATH.rb
+++ b/Library/Homebrew/PATH.rb
@@ -39,12 +39,12 @@ class PATH
     self
   end
 
-  sig { params(block: T.proc.params(arg0: String).returns(T::Boolean)).returns(T.self_type) }
+  sig { params(block: T.proc.params(arg0: String).returns(BasicObject)).returns(T.self_type) }
   def select(&block)
     self.class.new(@paths.select(&block))
   end
 
-  sig { params(block: T.proc.params(arg0: String).returns(T::Boolean)).returns(T.self_type) }
+  sig { params(block: T.proc.params(arg0: String).returns(BasicObject)).returns(T.self_type) }
   def reject(&block)
     self.class.new(@paths.reject(&block))
   end
diff --git a/Library/Homebrew/bundle/commands/exec.rb b/Library/Homebrew/bundle/commands/exec.rb
index 588de100e2..b6c698ff28 100644
--- a/Library/Homebrew/bundle/commands/exec.rb
+++ b/Library/Homebrew/bundle/commands/exec.rb
@@ -1,4 +1,4 @@
-# typed: false # rubocop:todo Sorbet/TrueSigil
+# typed: true
 # frozen_string_literal: true
 
 require "English"
@@ -13,6 +13,16 @@ module Homebrew
       module Exec
         PATH_LIKE_ENV_REGEX = /.+#{File::PATH_SEPARATOR}/
 
+        sig {
+          params(
+            args:       String,
+            global:     T::Boolean,
+            file:       T.nilable(String),
+            subcommand: String,
+            services:   T::Boolean,
+            check:      T::Boolean,
+          ).void
+        }
         def self.run(*args, global: false, file: nil, subcommand: "", services: false, check: false)
           if check
             require "bundle/commands/check"
@@ -25,9 +35,9 @@ module Homebrew
 
           # Setup Homebrew's ENV extensions
           ENV.activate_extensions!
-          raise UsageError, "No command to execute was specified!" if args.blank?
 
           command = args.first
+          raise UsageError, "No command to execute was specified!" if command.blank?
 
           require "bundle/brewfile"
           @dsl = Brewfile.read(global:, file:)
@@ -181,7 +191,7 @@ module Homebrew
           if services
             require "bundle/brew_services"
 
-            exit_code = 0
+            exit_code = T.let(0, Integer)
             run_services(@dsl.entries) do
               Kernel.system(*args)
               if (system_exit_code = $CHILD_STATUS&.exitstatus)
@@ -199,7 +209,7 @@ module Homebrew
             entries: T::Array[Homebrew::Bundle::Dsl::Entry],
             _block:  T.proc.params(
               entry:                Homebrew::Bundle::Dsl::Entry,
-              info:                 T::Hash[String, T.anything],
+              info:                 T::Hash[String, T.untyped],
               service_file:         Pathname,
               conflicting_services: T::Array[T::Hash[String, T.anything]],
             ).void,
@@ -279,7 +289,7 @@ module Homebrew
           map_service_info(entries) do |entry, info, service_file, conflicting_services|
             # Don't restart if already running this version
             loaded_file = Pathname.new(info["loaded_file"].to_s)
-            next if info["running"] && loaded_file&.file? && loaded_file&.realpath == service_file.realpath
+            next if info["running"] && loaded_file.file? && loaded_file.realpath == service_file.realpath
 
             if info["running"] && !Bundle::BrewServices.stop(info["name"], keep: true)
               opoo "Failed to stop #{info["name"]} service"
diff --git a/Library/Homebrew/cmd/--env.rb b/Library/Homebrew/cmd/--env.rb
index e0a2a50307..90f505942d 100644
--- a/Library/Homebrew/cmd/--env.rb
+++ b/Library/Homebrew/cmd/--env.rb
@@ -31,7 +31,7 @@ module Homebrew
       sig { override.void }
       def run
         ENV.activate_extensions!
-        T.cast(ENV, Superenv).deps = args.named.to_formulae if superenv?(nil)
+        ENV.deps = args.named.to_formulae if superenv?(nil)
         ENV.setup_build_environment
 
         shell = if args.plain?
diff --git a/Library/Homebrew/dependencies.rbi b/Library/Homebrew/dependencies.rbi
index 29a8508c06..5cdc3fcad4 100644
--- a/Library/Homebrew/dependencies.rbi
+++ b/Library/Homebrew/dependencies.rbi
@@ -13,8 +13,8 @@ class Dependencies < SimpleDelegator
   sig { returns(T::Enumerator[Dependency]) }
   def each(&blk); end
 
-  sig { params(blk: T.proc.params(arg0: Dependency).returns(T::Boolean)).returns(T::Array[Dependency]) }
-  sig { returns(T::Enumerator[Dependency]) }
+  sig { override.params(blk: T.proc.params(arg0: Dependency).returns(T.anything)).returns(T::Array[Dependency]) }
+  sig { override.returns(T::Enumerator[Dependency]) }
   def select(&blk); end
 end
 
@@ -26,7 +26,7 @@ class Requirements < SimpleDelegator
   sig { returns(T::Enumerator[Requirement]) }
   def each(&blk); end
 
-  sig { params(blk: T.proc.params(arg0: Requirement).returns(T::Boolean)).returns(T::Array[Requirement]) }
-  sig { returns(T::Enumerator[Requirement]) }
+  sig { override.params(blk: T.proc.params(arg0: Requirement).returns(T.anything)).returns(T::Array[Requirement]) }
+  sig { override.returns(T::Enumerator[Requirement]) }
   def select(&blk); end
 end
diff --git a/Library/Homebrew/dev-cmd/sh.rb b/Library/Homebrew/dev-cmd/sh.rb
index 2ba18a56e9..df034059fe 100644
--- a/Library/Homebrew/dev-cmd/sh.rb
+++ b/Library/Homebrew/dev-cmd/sh.rb
@@ -16,10 +16,10 @@ module Homebrew
           in an Xcode-only configuration since it adds tools like `make` to your `$PATH`
           which build systems would not find otherwise.
         EOS
-        flag   "--env=",
-               description: "Use the standard `$PATH` instead of superenv's when `std` is passed."
-        flag   "-c=", "--cmd=",
-               description: "Execute commands in a non-interactive shell."
+        flag "--env=",
+             description: "Use the standard `$PATH` instead of superenv's when `std` is passed."
+        flag "-c=", "--cmd=",
+             description: "Execute commands in a non-interactive shell."
 
         named_args :file, max: 1
       end
@@ -29,7 +29,9 @@ module Homebrew
         ENV.activate_extensions!(env: args.env)
 
         if superenv?(args.env)
-          T.cast(ENV, Superenv).deps = Formula.installed.select { |f| f.keg_only? && f.opt_prefix.directory? }
+          ENV.deps = Formula.installed.select do |f|
+            f.keg_only? && f.opt_prefix.directory?
+          end
         end
         ENV.setup_build_environment
         if superenv?(args.env)
diff --git a/Library/Homebrew/extend/ENV.rbi b/Library/Homebrew/extend/ENV.rbi
index 24711f725f..b7727c58c9 100644
--- a/Library/Homebrew/extend/ENV.rbi
+++ b/Library/Homebrew/extend/ENV.rbi
@@ -10,6 +10,10 @@ class Sorbet
     module Static
       class ENVClass
         include EnvActivation
+        # NOTE: This is a bit misleading, as at most only one of these can be true
+        # See: EnvActivation#activate_extensions!
+        include Stdenv
+        include Superenv
       end
     end
   end