diff --git a/Library/Homebrew/bottle_specification.rb b/Library/Homebrew/bottle_specification.rb
index 83d81f62cc..540a8fc5fd 100644
--- a/Library/Homebrew/bottle_specification.rb
+++ b/Library/Homebrew/bottle_specification.rb
@@ -9,7 +9,7 @@ class BottleSpecification
 
   attr_reader :collector
 
-  sig { returns(T::Hash[String, T.untyped]) }
+  sig { returns(T::Hash[Symbol, T.untyped]) }
   attr_reader :root_url_specs
 
   sig { returns(String) }
@@ -20,7 +20,7 @@ class BottleSpecification
     @rebuild = T.let(0, Integer)
     @repository = T.let(Homebrew::DEFAULT_REPOSITORY, String)
     @collector = T.let(Utils::Bottles::Collector.new, Utils::Bottles::Collector)
-    @root_url_specs = T.let({}, T::Hash[String, T.untyped])
+    @root_url_specs = T.let({}, T::Hash[Symbol, T.untyped])
     @root_url = T.let(nil, T.nilable(String))
   end
 
diff --git a/Library/Homebrew/build.rb b/Library/Homebrew/build.rb
index 702517fd03..fee6ecd7ff 100644
--- a/Library/Homebrew/build.rb
+++ b/Library/Homebrew/build.rb
@@ -135,9 +135,9 @@ class Build
     end
 
     new_env = {
-      "TMPDIR" => HOMEBREW_TEMP,
-      "TEMP"   => HOMEBREW_TEMP,
-      "TMP"    => HOMEBREW_TEMP,
+      "TMPDIR" => HOMEBREW_TEMP.to_s,
+      "TEMP"   => HOMEBREW_TEMP.to_s,
+      "TMP"    => HOMEBREW_TEMP.to_s,
     }
 
     with_env(new_env) do
diff --git a/Library/Homebrew/bundle/skipper.rb b/Library/Homebrew/bundle/skipper.rb
index c6b4ccd8f1..1261b5a621 100644
--- a/Library/Homebrew/bundle/skipper.rb
+++ b/Library/Homebrew/bundle/skipper.rb
@@ -37,11 +37,11 @@ module Homebrew
 
         private
 
-        sig { returns(T::Hash[Symbol, T::Array[String]]) }
+        sig { returns(T::Hash[Symbol, T.nilable(T::Array[String])]) }
         def skipped_entries
           return @skipped_entries if @skipped_entries
 
-          @skipped_entries ||= T.let({}, T.nilable(T::Hash[Symbol, T::Array[String]]))
+          @skipped_entries ||= T.let({}, T.nilable(T::Hash[Symbol, T.nilable(T::Array[String])]))
           [:brew, :cask, :mas, :tap, :whalebrew].each do |type|
             @skipped_entries[type] =
               ENV["HOMEBREW_BUNDLE_#{type.to_s.upcase}_SKIP"]&.split
diff --git a/Library/Homebrew/cask/config.rb b/Library/Homebrew/cask/config.rb
index 68b0f91e95..fbf5a426d1 100644
--- a/Library/Homebrew/cask/config.rb
+++ b/Library/Homebrew/cask/config.rb
@@ -12,6 +12,7 @@ module Cask
   #
   # @api internal
   class Config
+    ConfigHash = T.type_alias { T::Hash[Symbol, T.any(LazyObject, String, Pathname, T::Array[String])] }
     DEFAULT_DIRS = T.let(
       {
         appdir:               "/Applications",
@@ -33,7 +34,8 @@ module Cask
       T::Hash[Symbol, String],
     )
 
-    sig { returns(T::Hash[Symbol, String]) }
+    # runtime recursive evaluation forces the LazyObject to be evaluated
+    T::Sig::WithoutRuntime.sig { returns(T::Hash[Symbol, T.any(LazyObject, String)]) }
     def self.defaults
       {
         languages: LazyObject.new { ::OS::Mac.languages },
@@ -67,35 +69,25 @@ module Cask
 
     sig { params(json: String, ignore_invalid_keys: T::Boolean).returns(T.attached_class) }
     def self.from_json(json, ignore_invalid_keys: false)
-      config = JSON.parse(json)
+      config = JSON.parse(json, symbolize_names: true)
 
       new(
-        default:             config.fetch("default",  {}),
-        env:                 config.fetch("env",      {}),
-        explicit:            config.fetch("explicit", {}),
+        default:             config.fetch(:default,  {}),
+        env:                 config.fetch(:env,      {}),
+        explicit:            config.fetch(:explicit, {}),
         ignore_invalid_keys:,
       )
     end
 
-    sig {
-      params(
-        config: T::Enumerable[
-          [T.any(String, Symbol), T.any(String, Pathname, T::Array[String])],
-        ],
-      ).returns(
-        T::Hash[Symbol, T.any(String, Pathname, T::Array[String])],
-      )
-    }
+    sig { params(config: ConfigHash).returns(ConfigHash) }
     def self.canonicalize(config)
       config.to_h do |k, v|
-        key = k.to_sym
-
-        if DEFAULT_DIRS.key?(key)
+        if DEFAULT_DIRS.key?(k)
           raise TypeError, "Invalid path for default dir #{k}: #{v.inspect}" if v.is_a?(Array)
 
-          [key, Pathname(v).expand_path]
+          [k, Pathname(v.to_s).expand_path]
         else
-          [key, v]
+          [k, v]
         end
       end
     end
@@ -103,14 +95,14 @@ module Cask
     # Get the explicit configuration.
     #
     # @api internal
-    sig { returns(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]) }
+    sig { returns(ConfigHash) }
     attr_accessor :explicit
 
     sig {
       params(
-        default:             T.nilable(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]),
-        env:                 T.nilable(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]),
-        explicit:            T::Hash[Symbol, T.any(String, Pathname, T::Array[String])],
+        default:             T.nilable(ConfigHash),
+        env:                 T.nilable(ConfigHash),
+        explicit:            ConfigHash,
         ignore_invalid_keys: T::Boolean,
       ).void
     }
@@ -118,18 +110,18 @@ module Cask
       if default
         @default = T.let(
           self.class.canonicalize(self.class.defaults.merge(default)),
-          T.nilable(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]),
+          T.nilable(ConfigHash),
         )
       end
       if env
         @env = T.let(
           self.class.canonicalize(env),
-          T.nilable(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]),
+          T.nilable(ConfigHash),
         )
       end
       @explicit = T.let(
         self.class.canonicalize(explicit),
-        T::Hash[Symbol, T.any(String, Pathname, T::Array[String])],
+        ConfigHash,
       )
 
       if ignore_invalid_keys
@@ -142,18 +134,18 @@ module Cask
       @explicit.assert_valid_keys(*self.class.defaults.keys)
     end
 
-    sig { returns(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]) }
+    sig { returns(ConfigHash) }
     def default
       @default ||= self.class.canonicalize(self.class.defaults)
     end
 
-    sig { returns(T::Hash[Symbol, T.any(String, Pathname, T::Array[String])]) }
+    sig { returns(ConfigHash) }
     def env
       @env ||= self.class.canonicalize(
         Homebrew::EnvConfig.cask_opts
           .select { |arg| arg.include?("=") }
           .map { |arg| T.cast(arg.split("=", 2), [String, String]) }
-          .map do |(flag, value)|
+          .to_h do |(flag, value)|
             key = flag.sub(/^--/, "")
             # converts --language flag to :languages config key
             if key == "language"
@@ -161,7 +153,7 @@ module Cask
               value = value.split(",")
             end
 
-            [key, value]
+            [key.to_sym, value]
           end,
       )
     end
diff --git a/Library/Homebrew/cask/tab.rb b/Library/Homebrew/cask/tab.rb
index b6bc7a54da..d9804fa70c 100644
--- a/Library/Homebrew/cask/tab.rb
+++ b/Library/Homebrew/cask/tab.rb
@@ -11,7 +11,7 @@ module Cask
     sig { returns(T.nilable(T::Array[T.untyped])) }
     attr_accessor :uninstall_artifacts
 
-    sig { params(attributes: T::Hash[String, T.untyped]).void }
+    sig { params(attributes: T.any(T::Hash[String, T.untyped], T::Hash[Symbol, T.untyped])).void }
     def initialize(attributes = {})
       @uninstall_flight_blocks = T.let(nil, T.nilable(T::Boolean))
       @uninstall_artifacts = T.let(nil, T.nilable(T::Array[T.untyped]))
diff --git a/Library/Homebrew/cask/url.rb b/Library/Homebrew/cask/url.rb
index 71489fcdde..c87a7b2198 100644
--- a/Library/Homebrew/cask/url.rb
+++ b/Library/Homebrew/cask/url.rb
@@ -54,7 +54,7 @@ module Cask
         revisions:       T.nilable(T::Hash[T.any(Symbol, String), String]),
         revision:        T.nilable(String),
         trust_cert:      T.nilable(T::Boolean),
-        cookies:         T.nilable(T::Hash[String, String]),
+        cookies:         T.nilable(T::Hash[T.any(String, Symbol), String]),
         referer:         T.nilable(T.any(URI::Generic, String)),
         header:          T.nilable(T.any(String, T::Array[String])),
         user_agent:      T.nilable(T.any(Symbol, String)),
@@ -80,7 +80,8 @@ module Cask
       specs[:revisions]  = @revisions  = T.let(revisions, T.nilable(T::Hash[T.any(Symbol, String), String]))
       specs[:revision]   = @revision   = T.let(revision, T.nilable(String))
       specs[:trust_cert] = @trust_cert = T.let(trust_cert, T.nilable(T::Boolean))
-      specs[:cookies]    = @cookies    = T.let(cookies, T.nilable(T::Hash[String, String]))
+      specs[:cookies]    =
+        @cookies = T.let(cookies&.transform_keys(&:to_s), T.nilable(T::Hash[String, String]))
       specs[:referer]    = @referer    = T.let(referer, T.nilable(T.any(URI::Generic, String)))
       specs[:headers]    = @header     = T.let(header, T.nilable(T.any(String, T::Array[String])))
       specs[:user_agent] = @user_agent = T.let(user_agent || :default, T.nilable(T.any(Symbol, String)))
diff --git a/Library/Homebrew/cask_dependent.rb b/Library/Homebrew/cask_dependent.rb
index 01bd0a7f19..815bc9050b 100644
--- a/Library/Homebrew/cask_dependent.rb
+++ b/Library/Homebrew/cask_dependent.rb
@@ -45,7 +45,7 @@ class CaskDependent
     )
   end
 
-  sig { returns(T::Array[CaskDependent::Requirement]) }
+  sig { returns(T::Array[::Requirement]) }
   def requirements
     @requirements ||= T.let(
       begin
@@ -73,7 +73,7 @@ class CaskDependent
 
         requirements
       end,
-      T.nilable(T::Array[CaskDependent::Requirement]),
+      T.nilable(T::Array[::Requirement]),
     )
   end
 
diff --git a/Library/Homebrew/cli/args.rb b/Library/Homebrew/cli/args.rb
index f3358bfc10..c6e0eb9b47 100644
--- a/Library/Homebrew/cli/args.rb
+++ b/Library/Homebrew/cli/args.rb
@@ -9,7 +9,7 @@ module Homebrew
       #   1: long option name (e.g. "--debug")
       #   2: option description (e.g. "Print debugging information")
       #   3: whether the option is hidden
-      OptionsType = T.type_alias { T::Array[[String, T.nilable(String), String, T::Boolean]] }
+      OptionsType = T.type_alias { T::Array[[T.nilable(String), T.nilable(String), String, T::Boolean]] }
 
       sig { returns(T::Array[String]) }
       attr_reader :options_only, :flags_only, :remaining
@@ -170,7 +170,7 @@ module Homebrew
       sig { returns(T::Array[String]) }
       def cli_args
         @cli_args ||= @processed_options.filter_map do |short, long|
-          option = long || short
+          option = T.must(long || short)
           switch = :"#{option_to_name(option)}?"
           flag = option_to_name(option).to_sym
           if @table[switch] == true || @table[flag] == true
diff --git a/Library/Homebrew/cmd/outdated.rb b/Library/Homebrew/cmd/outdated.rb
index 6b4d81f179..3b9761c2dd 100644
--- a/Library/Homebrew/cmd/outdated.rb
+++ b/Library/Homebrew/cmd/outdated.rb
@@ -127,9 +127,7 @@ module Homebrew
       sig {
         params(
           formulae_or_casks: T::Array[T.any(Formula, Cask::Cask)],
-        ).returns(
-          T::Array[T.any(T::Hash[String, T.untyped], T::Hash[String, T.untyped])],
-        )
+        ).returns(T::Array[T::Hash[Symbol, T.untyped]])
       }
       def json_info(formulae_or_casks)
         formulae_or_casks.map do |formula_or_cask|
diff --git a/Library/Homebrew/cmd/update-report.rb b/Library/Homebrew/cmd/update-report.rb
index 9419a9eb2d..54f2d39718 100644
--- a/Library/Homebrew/cmd/update-report.rb
+++ b/Library/Homebrew/cmd/update-report.rb
@@ -427,6 +427,19 @@ require "extend/os/cmd/update-report"
 class Reporter
   include Utils::Output::Mixin
 
+  Report = T.type_alias do
+    {
+      A:  T::Array[String],
+      AC: T::Array[String],
+      D:  T::Array[String],
+      DC: T::Array[String],
+      M:  T::Array[String],
+      MC: T::Array[String],
+      R:  T::Array[[String, String]],
+      RC: T::Array[[String, String]],
+    }
+  end
+
   class ReporterRevisionUnsetError < RuntimeError
     sig { params(var_name: String).void }
     def initialize(var_name)
@@ -456,14 +469,17 @@ class Reporter
       raise ReporterRevisionUnsetError, current_revision_var if @current_revision.empty?
     end
 
-    @report = T.let(nil, T.nilable(T::Hash[Symbol, T::Array[String]]))
+    @report = T.let(nil, T.nilable(Report))
   end
 
-  sig { params(auto_update: T::Boolean).returns(T::Hash[Symbol, T::Array[String]]) }
+  sig { params(auto_update: T::Boolean).returns(Report) }
   def report(auto_update: false)
     return @report if @report
 
-    @report = Hash.new { |h, k| h[k] = [] }
+    @report = {
+      A: [], AC: [], D: [], DC: [], M: [], MC: [], R: T.let([], T::Array[[String, String]]),
+      RC: T.let([], T::Array[[String, String]])
+    }
     return @report unless updated?
 
     diff.each_line do |line|
@@ -791,13 +807,15 @@ class ReporterHub
 
   sig { void }
   def initialize
-    @hash = T.let({}, T::Hash[Symbol, T::Array[String]])
+    @hash = T.let({}, T::Hash[Symbol, T::Array[T.any(String, [String, String])]])
     @reporters = T.let([], T::Array[Reporter])
   end
 
   sig { params(key: Symbol).returns(T::Array[String]) }
   def select_formula_or_cask(key)
-    @hash.fetch(key, [])
+    raise "Unsupported key #{key}" unless [:A, :AC, :D, :DC, :M, :MC].include?(key)
+
+    T.cast(@hash.fetch(key, []), T::Array[String])
   end
 
   sig { params(reporter: Reporter, auto_update: T::Boolean).void }
diff --git a/Library/Homebrew/commands.rb b/Library/Homebrew/commands.rb
index 421866524d..6beee3bab9 100644
--- a/Library/Homebrew/commands.rb
+++ b/Library/Homebrew/commands.rb
@@ -204,7 +204,7 @@ module Commands
       cmd_parser.processed_options.filter_map do |short, long, desc, hidden|
         next if hidden
 
-        [long || short, desc]
+        [T.must(long || short), desc]
       end
     else
       options = []
diff --git a/Library/Homebrew/dependency_collector.rb b/Library/Homebrew/dependency_collector.rb
index 68e68c3fa9..3724f97cd4 100644
--- a/Library/Homebrew/dependency_collector.rb
+++ b/Library/Homebrew/dependency_collector.rb
@@ -135,7 +135,7 @@ class DependencyCollector
 
   sig {
     params(spec: T.any(String, Resource, Symbol, Requirement, Dependency, Class),
-           tags: T::Array[Symbol]).returns(T.any(Dependency, Requirement, Array, NilClass))
+           tags: T::Array[T.any(String, Symbol)]).returns(T.any(Dependency, Requirement, Array, NilClass))
   }
   def parse_spec(spec, tags)
     raise ArgumentError, "Implicit dependencies cannot be manually specified" if tags.include?(:implicit)
diff --git a/Library/Homebrew/dev-cmd/bottle.rb b/Library/Homebrew/dev-cmd/bottle.rb
index 5abeb8d0f4..7fb25e4a56 100644
--- a/Library/Homebrew/dev-cmd/bottle.rb
+++ b/Library/Homebrew/dev-cmd/bottle.rb
@@ -181,7 +181,7 @@ module Homebrew
       end
 
       sig {
-        params(old_keys: T::Array[String], old_bottle_spec: BottleSpecification,
+        params(old_keys: T::Array[Symbol], old_bottle_spec: BottleSpecification,
                new_bottle_hash: T::Hash[String, T.untyped])
           .returns([T::Array[String], T::Array[T::Hash[Symbol, T.any(String, Symbol)]]])
       }
@@ -506,7 +506,7 @@ module Homebrew
             tab.time = nil
             tab.changed_files = changed_files.dup
             if args.only_json_tab?
-              tab.changed_files.delete(Pathname.new(AbstractTab::FILENAME))
+              tab.changed_files&.delete(Pathname.new(AbstractTab::FILENAME))
               tab.tabfile.unlink
             else
               tab.write
diff --git a/Library/Homebrew/dev-cmd/tests.rb b/Library/Homebrew/dev-cmd/tests.rb
index dc742876bf..0780be102d 100644
--- a/Library/Homebrew/dev-cmd/tests.rb
+++ b/Library/Homebrew/dev-cmd/tests.rb
@@ -119,7 +119,7 @@ module Homebrew
           # seeds being output when running parallel tests.
           seed = args.seed || rand(0xFFFF).to_i
 
-          bundle_args = ["-I", HOMEBREW_LIBRARY_PATH/"test"]
+          bundle_args = ["-I", (HOMEBREW_LIBRARY_PATH/"test").to_s]
           bundle_args += %W[
             --seed #{seed}
             --color
@@ -249,6 +249,7 @@ module Homebrew
         ENV["HOMEBREW_TEST_GENERIC_OS"] = "1" if args.generic?
         ENV["HOMEBREW_TEST_ONLINE"] = "1" if args.online?
         ENV["HOMEBREW_SORBET_RUNTIME"] = "1"
+        ENV["HOMEBREW_SORBET_RECURSIVE"] = "1"
 
         ENV["USER"] ||= system_command!("id", args: ["-nu"]).stdout.chomp
 
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index b00517b557..9dbcb63ce9 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -1198,9 +1198,9 @@ module Homebrew
 
       private
 
-      sig { returns(T::Array[Pathname]) }
+      sig { returns(T::Array[String]) }
       def paths
-        @paths ||= T.let(ORIGINAL_PATHS.uniq.map(&:to_s), T.nilable(T::Array[Pathname]))
+        @paths ||= T.let(ORIGINAL_PATHS.uniq.map(&:to_s), T.nilable(T::Array[String]))
       end
     end
   end
diff --git a/Library/Homebrew/download_strategy.rb b/Library/Homebrew/download_strategy.rb
index 5353ee2862..c70cbce062 100644
--- a/Library/Homebrew/download_strategy.rb
+++ b/Library/Homebrew/download_strategy.rb
@@ -643,11 +643,9 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
     args
   end
 
-  sig { returns(T::Hash[Symbol, String]) }
+  sig { returns(T::Hash[Symbol, T.any(String, Symbol)]) }
   def _curl_opts
-    return { user_agent: meta.fetch(:user_agent) } if meta.key?(:user_agent)
-
-    {}
+    meta.slice(:user_agent)
   end
 
   sig { override.params(args: String, options: T.untyped).returns(SystemCommand::Result) }
diff --git a/Library/Homebrew/env_config.rb b/Library/Homebrew/env_config.rb
index 328bd734f8..40bdbadbbd 100644
--- a/Library/Homebrew/env_config.rb
+++ b/Library/Homebrew/env_config.rb
@@ -471,6 +471,11 @@ module Homebrew
                      "of macOS. This is useful in development on new macOS versions.",
         boolean:     true,
       },
+      HOMEBREW_SORBET_RECURSIVE:                 {
+        description: "If set along with `$HOMEBREW_SORBET_RUNTIME`, enable recursive typechecking using Sorbet. " \
+                     "Auomatically enabled when running tests.",
+        boolean:     true,
+      },
       HOMEBREW_SORBET_RUNTIME:                   {
         description: "If set, enable runtime typechecking using Sorbet. " \
                      "Set by default for `$HOMEBREW_DEVELOPER` or when running some developer commands.",
diff --git a/Library/Homebrew/extend/ENV/super.rb b/Library/Homebrew/extend/ENV/super.rb
index 03fe313b47..0fca6cc7a3 100644
--- a/Library/Homebrew/extend/ENV/super.rb
+++ b/Library/Homebrew/extend/ENV/super.rb
@@ -244,7 +244,7 @@ module Superenv
     end
 
     # Don't add `llvm` to library paths; this leads to undesired linkage to LLVM's `libunwind`
-    paths << keg_only_deps.reject { |dep| dep.name.match?(/^llvm(@\d+)?$/) }
+    paths += keg_only_deps.reject { |dep| dep.name.match?(/^llvm(@\d+)?$/) }
                           .map(&:opt_lib)
     paths << (HOMEBREW_PREFIX/"lib")
 
diff --git a/Library/Homebrew/extend/kernel.rb b/Library/Homebrew/extend/kernel.rb
index a38121b094..6b6454dc4f 100644
--- a/Library/Homebrew/extend/kernel.rb
+++ b/Library/Homebrew/extend/kernel.rb
@@ -34,7 +34,7 @@ module Kernel
 
   sig { type_parameters(:U).params(block: T.proc.returns(T.type_parameter(:U))).returns(T.type_parameter(:U)) }
   def with_homebrew_path(&block)
-    with_env(PATH: PATH.new(ORIGINAL_PATHS), &block)
+    with_env(PATH: PATH.new(ORIGINAL_PATHS).to_s, &block)
   end
 
   sig {
@@ -283,8 +283,10 @@ module Kernel
   # @api public
   sig {
     type_parameters(:U)
-      .params(hash: T::Hash[Object, String], _block: T.proc.returns(T.type_parameter(:U)))
-      .returns(T.type_parameter(:U))
+      .params(
+        hash:   T::Hash[Object, T.any(NilClass, PATH, Pathname, String)],
+        _block: T.proc.returns(T.type_parameter(:U)),
+      ).returns(T.type_parameter(:U))
   }
   def with_env(hash, &_block)
     old_values = {}
@@ -292,7 +294,7 @@ module Kernel
       hash.each do |key, value|
         key = key.to_s
         old_values[key] = ENV.delete(key)
-        ENV[key] = value
+        ENV[key] = value&.to_s
       end
 
       yield
diff --git a/Library/Homebrew/extend/os/linux/cask/config.rb b/Library/Homebrew/extend/os/linux/cask/config.rb
index 756cc7bae1..c9184fea82 100644
--- a/Library/Homebrew/extend/os/linux/cask/config.rb
+++ b/Library/Homebrew/extend/os/linux/cask/config.rb
@@ -15,7 +15,7 @@ module OS
             appdir:         "~/.config/apps",
           }.freeze, T::Hash[Symbol, String])
 
-          sig { returns(T::Hash[Symbol, String]) }
+          sig { returns(T::Hash[Symbol, T.any(LazyObject, String)]) }
           def defaults
             {
               languages: LazyObject.new { Linux.languages },
diff --git a/Library/Homebrew/formula.rb b/Library/Homebrew/formula.rb
index 33560d6e04..a1e0720544 100644
--- a/Library/Homebrew/formula.rb
+++ b/Library/Homebrew/formula.rb
@@ -3963,7 +3963,7 @@ class Formula
     # ```
     #
     # @api public
-    sig { params(dep: T.any(String, Symbol, T::Hash[String, T.untyped], T::Class[Requirement])).void }
+    sig { params(dep: T.any(String, Symbol, T::Hash[T.any(String, Symbol, T::Class[Requirement]), T.untyped], T::Class[Requirement])).void }
     def depends_on(dep)
       specs.each { |spec| spec.depends_on(dep) }
     end
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 08107df5af..6e714d12ee 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -809,7 +809,7 @@ on_request: installed_on_request?, options:)
     else
       []
     end
-    options += effective_build_options_for(formula).used_options.to_a
+    options += effective_build_options_for(formula).used_options.to_a.map(&:to_s)
     options
   end
 
diff --git a/Library/Homebrew/formulary.rb b/Library/Homebrew/formulary.rb
index b9bad8ecf3..60daf254d9 100644
--- a/Library/Homebrew/formulary.rb
+++ b/Library/Homebrew/formulary.rb
@@ -51,7 +51,14 @@ module Formulary
   end
   private_class_method :platform_cache_tag
 
-  sig { returns(T::Hash[Symbol, T::Hash[String, T.class_of(Formula)]]) }
+  sig {
+    returns({
+      api:               T.nilable(T::Hash[String, T.class_of(Formula)]),
+      formulary_factory: T.nilable(T::Hash[String, Formula]),
+      path:              T.nilable(T::Hash[String, T.class_of(Formula)]),
+      stub:              T.nilable(T::Hash[String, T.class_of(Formula)]),
+    })
+  }
   def self.platform_cache
     cache[platform_cache_tag] ||= {}
   end
diff --git a/Library/Homebrew/lazy_object.rb b/Library/Homebrew/lazy_object.rb
index c99bcb4db3..a09c92ed7a 100644
--- a/Library/Homebrew/lazy_object.rb
+++ b/Library/Homebrew/lazy_object.rb
@@ -28,4 +28,7 @@ class LazyObject < Delegator
 
     __getobj__.is_a?(klass) || super
   end
+
+  def class = __getobj__.class
+  def to_s = __getobj__.to_s
 end
diff --git a/Library/Homebrew/messages.rb b/Library/Homebrew/messages.rb
index 49b2ebd5c3..5c1317abb8 100644
--- a/Library/Homebrew/messages.rb
+++ b/Library/Homebrew/messages.rb
@@ -14,7 +14,7 @@ class Messages
   sig { returns(Integer) }
   attr_reader :package_count
 
-  sig { returns(T::Array[T::Hash[String, Float]]) }
+  sig { returns(T::Array[{ package: String, time: Float }]) }
   attr_reader :install_times
 
   sig { void }
@@ -22,7 +22,7 @@ class Messages
     @caveats = T.let([], T::Array[{ package: String, caveats: T.any(String, Caveats) }])
     @completions_and_elisp = T.let(Set.new, T::Set[String])
     @package_count = T.let(0, Integer)
-    @install_times = T.let([], T::Array[T::Hash[String, Float]])
+    @install_times = T.let([], T::Array[{ package: String, time: Float }])
   end
 
   sig { params(package: String, caveats: T.any(String, Caveats)).void }
diff --git a/Library/Homebrew/requirements/xcode_requirement.rb b/Library/Homebrew/requirements/xcode_requirement.rb
index c0c9134238..abc31503ce 100644
--- a/Library/Homebrew/requirements/xcode_requirement.rb
+++ b/Library/Homebrew/requirements/xcode_requirement.rb
@@ -15,10 +15,10 @@ class XcodeRequirement < Requirement
     xcode_installed_version!
   end
 
-  sig { params(tags: T::Array[String]).void }
+  sig { params(tags: T::Array[T.any(String, Symbol)]).void }
   def initialize(tags = [])
     version = tags.shift if tags.first.to_s.match?(/(\d\.)+\d/)
-    @version = T.let(version, T.nilable(String))
+    @version = T.let(version.to_s, T.nilable(String))
     super
   end
 
diff --git a/Library/Homebrew/rubocops/cask/ast/stanza.rb b/Library/Homebrew/rubocops/cask/ast/stanza.rb
index cab7d606e4..8bd68c6539 100644
--- a/Library/Homebrew/rubocops/cask/ast/stanza.rb
+++ b/Library/Homebrew/rubocops/cask/ast/stanza.rb
@@ -83,11 +83,11 @@ module RuboCop
           )
         end
 
-        sig { returns(T::Hash[Parser::Source::Range, T::Array[Parser::Source::Comment]]) }
+        sig { returns(T::Hash[Parser::Source::Map, T::Array[Parser::Source::Comment]]) }
         def comments_hash
           @comments_hash ||= T.let(
             Parser::Source::Comment.associate_locations(stanza_node.parent, all_comments),
-            T.nilable(T::Hash[Parser::Source::Range, T::Array[Parser::Source::Comment]]),
+            T.nilable(T::Hash[Parser::Source::Map, T::Array[Parser::Source::Comment]]),
           )
         end
 
diff --git a/Library/Homebrew/rubocops/cask/mixin/cask_help.rb b/Library/Homebrew/rubocops/cask/mixin/cask_help.rb
index 61bd3643a8..d9d43ec445 100644
--- a/Library/Homebrew/rubocops/cask/mixin/cask_help.rb
+++ b/Library/Homebrew/rubocops/cask/mixin/cask_help.rb
@@ -46,7 +46,7 @@ module RuboCop
         sig {
           params(
             block_node: RuboCop::AST::BlockNode,
-            comments:   T::Array[String],
+            comments:   T::Array[Parser::Source::Comment],
           ).returns(
             T::Array[RuboCop::Cask::AST::Stanza],
           )
diff --git a/Library/Homebrew/sbom.rb b/Library/Homebrew/sbom.rb
index b0b463a004..5607b12f06 100644
--- a/Library/Homebrew/sbom.rb
+++ b/Library/Homebrew/sbom.rb
@@ -13,7 +13,7 @@ class SBOM
   include Utils::Output::Mixin
 
   FILENAME = "sbom.spdx.json"
-  SCHEMA_FILE = (HOMEBREW_LIBRARY_PATH/"data/schemas/sbom.json").freeze
+  SCHEMA_FILE = T.let((HOMEBREW_LIBRARY_PATH/"data/schemas/sbom.json").freeze, Pathname)
 
   # Instantiates a {SBOM} for a new installation of a formula.
   sig { params(formula: Formula, tab: Tab).returns(T.attached_class) }
@@ -62,7 +62,7 @@ class SBOM
     formula.prefix/FILENAME
   end
 
-  sig { params(deps: T::Array[T::Hash[String, String]]).returns(T::Array[T::Hash[String, String]]) }
+  sig { params(deps: T::Array[T::Hash[String, T.untyped]]).returns(T::Array[T::Hash[String, T.anything]]) }
   def self.runtime_deps_hash(deps)
     deps.map do |dep|
       full_name = dep.fetch("full_name")
@@ -83,12 +83,12 @@ class SBOM
     spdxfile(formula).exist?
   end
 
-  sig { returns(T::Hash[String, T.untyped]) }
+  sig { returns(T::Hash[String, T.anything]) }
   def self.schema
-    @schema ||= JSON.parse(SCHEMA_FILE.read, freeze: true)
+    @schema ||= T.let(JSON.parse(SCHEMA_FILE.read, freeze: true), T.nilable(T::Hash[String, T.untyped]))
   end
 
-  sig { params(bottling: T::Boolean).returns(T::Array[T::Hash[String, T.untyped]]) }
+  sig { params(bottling: T::Boolean).returns(T::Array[String]) }
   def schema_validation_errors(bottling: false)
     unless Homebrew.require? "json_schemer"
       error_message = "Need json_schemer to validate SBOM, run `brew install-bundler-gems --add-groups=bottle`!"
@@ -134,17 +134,17 @@ class SBOM
   attr_reader :name, :homebrew_version, :time, :stdlib, :source, :built_on, :license
   attr_accessor :spdxfile
 
-  sig { params(attributes: Hash).void }
+  sig { params(attributes: T::Hash[Symbol, T.untyped]).void }
   def initialize(attributes = {})
     attributes.each { |key, value| instance_variable_set(:"@#{key}", value) }
   end
 
   sig {
     params(
-      runtime_dependency_declaration: T::Array[Hash],
-      compiler_declaration:           Hash,
+      runtime_dependency_declaration: T::Array[T::Hash[Symbol, T.untyped]],
+      compiler_declaration:           T::Hash[String, T.untyped],
       bottling:                       T::Boolean,
-    ).returns(T::Array[Hash])
+    ).returns(T::Array[T::Hash[Symbol, T.untyped]])
   }
   def generate_relations_json(runtime_dependency_declaration, compiler_declaration, bottling:)
     runtime = runtime_dependency_declaration.map do |dependency|
@@ -167,7 +167,7 @@ class SBOM
       spdxElementId:      "SPDXRef-File-#{name}",
       relationshipType:   "PACKAGE_OF",
       relatedSpdxElement: "SPDXRef-Archive-#{name}-src",
-    }], T::Array[Hash])
+    }], T::Array[T::Hash[Symbol, T.untyped]])
 
     unless bottling
       base << {
@@ -189,16 +189,11 @@ class SBOM
   end
 
   sig {
-    params(runtime_dependency_declaration: T::Array[Hash],
-           compiler_declaration:           Hash,
-           bottling:                       T::Boolean).returns(
-             T::Array[
-              T::Hash[
-                Symbol,
-                T.any(String, T::Array[T::Hash[Symbol, String]]),
-              ],
-            ],
-           )
+    params(
+      runtime_dependency_declaration: T::Array[T::Hash[Symbol, T.anything]],
+      compiler_declaration:           T::Hash[String, T::Hash[Symbol, T.anything]],
+      bottling:                       T::Boolean,
+    ).returns(T::Array[T::Hash[Symbol, T.untyped]])
   }
   def generate_packages_json(runtime_dependency_declaration, compiler_declaration, bottling:)
     bottle = []
@@ -259,9 +254,8 @@ class SBOM
   end
 
   sig {
-    params(bottling: T::Boolean).returns(T::Array[T::Hash[Symbol,
-                                                          T.any(T::Boolean, String,
-                                                                T::Array[T::Hash[Symbol, String]])]])
+    params(bottling: T::Boolean)
+      .returns(T::Array[T::Hash[Symbol, T.any(T::Boolean, String, T::Array[T::Hash[Symbol, String]])]])
   }
   def full_spdx_runtime_dependencies(bottling:)
     return [] if bottling || @runtime_dependencies.blank?
@@ -302,7 +296,7 @@ class SBOM
     end
   end
 
-  sig { params(bottling: T::Boolean).returns(T::Hash[Symbol, T.any(String, T::Array[T::Hash[Symbol, String]])]) }
+  sig { params(bottling: T::Boolean).returns(T::Hash[Symbol, T.anything]) }
   def to_spdx_sbom(bottling:)
     runtime_full = full_spdx_runtime_dependencies(bottling:)
 
@@ -360,7 +354,7 @@ class SBOM
     }
   end
 
-  sig { params(base: T.nilable(T::Hash[String, Hash])).returns(T.nilable(T::Hash[String, String])) }
+  sig { params(base: T.nilable(T::Hash[String, T.untyped])).returns(T.nilable(T::Hash[String, String])) }
   def get_bottle_info(base)
     return unless base.present?
 
diff --git a/Library/Homebrew/service.rb b/Library/Homebrew/service.rb
index 9d648e2c54..b9ac0a41bf 100644
--- a/Library/Homebrew/service.rb
+++ b/Library/Homebrew/service.rb
@@ -337,7 +337,7 @@ module Homebrew
       parsed
     end
 
-    sig { params(variables: T::Hash[Symbol, String]).returns(T.nilable(T::Hash[Symbol, String])) }
+    sig { params(variables: T::Hash[Symbol, T.any(Pathname, String)]).returns(T.nilable(T::Hash[Symbol, String])) }
     def environment_variables(variables = {})
       @environment_variables = variables.transform_values(&:to_s)
     end
diff --git a/Library/Homebrew/software_spec.rb b/Library/Homebrew/software_spec.rb
index 82435a9a28..0f909685a1 100644
--- a/Library/Homebrew/software_spec.rb
+++ b/Library/Homebrew/software_spec.rb
@@ -219,7 +219,7 @@ class SoftwareSpec
     options << opt
   end
 
-  sig { params(hash: T::Hash[T.any(String, Symbol), T.any(String, Symbol)]).void }
+  sig { params(hash: T::Hash[T.any(String, Symbol, T::Array[String]), T.any(String, Symbol, T::Array[String])]).void }
   def deprecated_option(hash)
     raise ArgumentError, "deprecated_option hash must not be empty" if hash.empty?
 
@@ -242,7 +242,7 @@ class SoftwareSpec
     @build = BuildOptions.new(Options.create(@flags), options)
   end
 
-  sig { params(spec: T.any(String, Symbol, T::Hash[String, T.untyped], T::Class[Requirement], Dependable)).void }
+  sig { params(spec: T.any(String, Symbol, T::Hash[T.any(String, Symbol, T::Class[Requirement]), T.untyped], T::Class[Requirement], Dependable)).void }
   def depends_on(spec)
     dep = dependency_collector.add(spec)
     add_dep_option(dep) if dep
diff --git a/Library/Homebrew/standalone/sorbet.rb b/Library/Homebrew/standalone/sorbet.rb
index 406582618d..332356f5c5 100644
--- a/Library/Homebrew/standalone/sorbet.rb
+++ b/Library/Homebrew/standalone/sorbet.rb
@@ -10,6 +10,55 @@ require "extend/module"
 # There are mechanisms to achieve a middle ground (`default_checked_level`).
 if ENV["HOMEBREW_SORBET_RUNTIME"]
   T::Configuration.enable_final_checks_on_hooks
+  if ENV["HOMEBREW_SORBET_RECURSIVE"] == "1"
+    module T
+      module Types
+        class FixedArray < Base
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class FixedHash < Base
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class Intersection < Base
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedArray < TypedEnumerable
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedEnumerable < Base
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedEnumeratorChain < TypedEnumerable
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedEnumeratorLazy < TypedEnumerable
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedHash < TypedEnumerable
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedRange < TypedEnumerable
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class TypedSet < TypedEnumerable
+          def valid?(obj) = recursively_valid?(obj)
+        end
+
+        class Union < Base
+          def valid?(obj) = recursively_valid?(obj)
+        end
+      end
+    end
+  end
 else
   # Redefine `T.let`, etc. to make the `checked` parameter default to `false` rather than `true`.
   # @private
diff --git a/Library/Homebrew/system_command.rb b/Library/Homebrew/system_command.rb
index 39f9975e16..3f6f6fc230 100644
--- a/Library/Homebrew/system_command.rb
+++ b/Library/Homebrew/system_command.rb
@@ -27,7 +27,7 @@ class SystemCommand
         args:         T::Array[T.any(String, Integer, Float, Pathname, URI::Generic)],
         sudo:         T::Boolean,
         sudo_as_root: T::Boolean,
-        env:          T::Hash[String, String],
+        env:          T::Hash[String, T.any(NilClass, String, T::Boolean)],
         input:        T.any(String, T::Array[String]),
         must_succeed: T::Boolean,
         print_stdout: T.any(T::Boolean, Symbol),
@@ -56,7 +56,7 @@ class SystemCommand
         args:         T::Array[T.any(String, Integer, Float, Pathname, URI::Generic)],
         sudo:         T::Boolean,
         sudo_as_root: T::Boolean,
-        env:          T::Hash[String, String],
+        env:          T::Hash[String, T.any(NilClass, String, T::Boolean)],
         input:        T.any(String, T::Array[String]),
         print_stdout: T.any(T::Boolean, Symbol),
         print_stderr: T.any(T::Boolean, Symbol),
@@ -84,7 +84,7 @@ class SystemCommand
       args:         T::Array[T.any(String, Integer, Float, Pathname, URI::Generic)],
       sudo:         T::Boolean,
       sudo_as_root: T::Boolean,
-      env:          T::Hash[String, String],
+      env:          T::Hash[String, T.any(NilClass, String, T::Boolean)],
       input:        T.any(String, T::Array[String]),
       must_succeed: T::Boolean,
       print_stdout: T.any(T::Boolean, Symbol),
@@ -110,7 +110,7 @@ class SystemCommand
       args:         T::Array[T.any(String, Integer, Float, Pathname, URI::Generic)],
       sudo:         T::Boolean,
       sudo_as_root: T::Boolean,
-      env:          T::Hash[String, String],
+      env:          T::Hash[String, T.any(NilClass, String, T::Boolean)],
       input:        T.any(String, T::Array[String]),
       must_succeed: T::Boolean,
       print_stdout: T.any(T::Boolean, Symbol),
@@ -169,7 +169,7 @@ class SystemCommand
       args:         T::Array[T.any(String, Integer, Float, Pathname, URI::Generic)],
       sudo:         T::Boolean,
       sudo_as_root: T::Boolean,
-      env:          T::Hash[String, String],
+      env:          T::Hash[String, T.any(NilClass, String, T::Boolean)],
       input:        T.any(String, T::Array[String]),
       must_succeed: T::Boolean,
       print_stdout: T.any(T::Boolean, Symbol),
@@ -237,7 +237,7 @@ class SystemCommand
   sig { returns(T.any(NilClass, String, Pathname)) }
   attr_reader :chdir
 
-  sig { returns(T::Hash[String, String]) }
+  sig { returns(T::Hash[String, T.any(NilClass, String, T::Boolean)]) }
   attr_reader :env
 
   sig { returns(T::Boolean) }
@@ -378,7 +378,7 @@ class SystemCommand
 
   sig {
     params(
-      env:        T::Hash[String, String],
+      env:        T::Hash[String, T.nilable(String)],
       executable: String,
       args:       String,
       options:    T.untyped,
@@ -480,7 +480,7 @@ class SystemCommand
     sig {
       params(
         command: T::Array[String],
-        output:  T::Array[[Symbol, String]],
+        output:  T::Array[[T.any(String, Symbol), String]],
         status:  Process::Status,
         secrets: T::Array[String],
       ).void
diff --git a/Library/Homebrew/tab.rb b/Library/Homebrew/tab.rb
index 9acea83252..1f5985b5f1 100644
--- a/Library/Homebrew/tab.rb
+++ b/Library/Homebrew/tab.rb
@@ -38,7 +38,8 @@ class AbstractTab
   # @api internal
   attr_accessor :runtime_dependencies
 
-  sig { params(attributes: T::Hash[String, T.untyped]).void }
+  # TODO: Update attributes to only accept symbol keys (kwargs style).
+  sig { params(attributes: T.any(T::Hash[String, T.untyped], T::Hash[Symbol, T.untyped])).void }
   def initialize(attributes = {})
     @installed_as_dependency = T.let(nil, T.nilable(T::Boolean))
     @installed_on_request = T.let(nil, T.nilable(T::Boolean))
@@ -51,7 +52,14 @@ class AbstractTab
     @built_on = T.let(nil, T.nilable(T::Hash[String, T.untyped]))
     @runtime_dependencies = T.let(nil, T.nilable(T::Array[T.untyped]))
 
-    attributes.each { |key, value| instance_variable_set(:"@#{key}", value) }
+    attributes.each do |key, value|
+      case key.to_sym
+      when :changed_files
+        @changed_files = value&.map { |f| Pathname(f) }
+      else
+        instance_variable_set(:"@#{key}", value)
+      end
+    end
   end
 
   # Instantiates a {Tab} for a new installation of a formula or cask.
@@ -166,15 +174,18 @@ class Tab < AbstractTab
   # @api internal
   attr_accessor :poured_from_bottle
 
-  attr_accessor :built_as_bottle, :changed_files, :stdlib, :aliases
+  attr_accessor :built_as_bottle, :stdlib, :aliases
   attr_writer :used_options, :unused_options, :compiler, :source_modified_time
   attr_reader :tapped_from
 
-  sig { params(attributes: T::Hash[String, T.untyped]).void }
+  sig { returns(T.nilable(T::Array[Pathname])) }
+  attr_accessor :changed_files
+
+  sig { params(attributes: T.any(T::Hash[String, T.untyped], T::Hash[Symbol, T.untyped])).void }
   def initialize(attributes = {})
     @poured_from_bottle = T.let(nil, T.nilable(T::Boolean))
     @built_as_bottle = T.let(nil, T.nilable(T::Boolean))
-    @changed_files = T.let(nil, T.nilable(T::Array[Pathname]))
+    @changed_files = nil
     @stdlib = T.let(nil, T.nilable(String))
     @aliases = T.let(nil, T.nilable(T::Array[String]))
     @used_options = T.let(nil, T.nilable(T::Array[String]))
diff --git a/Library/Homebrew/test/cmd/update-report_spec.rb b/Library/Homebrew/test/cmd/update-report_spec.rb
index 50363220c1..3b919200bf 100644
--- a/Library/Homebrew/test/cmd/update-report_spec.rb
+++ b/Library/Homebrew/test/cmd/update-report_spec.rb
@@ -83,7 +83,7 @@ RSpec.describe Homebrew::Cmd::UpdateReport do
 
       expect(hub.select_formula_or_cask(:A)).to be_empty
       expect(hub.select_formula_or_cask(:D)).to be_empty
-      expect(hub.select_formula_or_cask(:R)).to eq([["cv", "progress"]])
+      expect(hub.instance_variable_get(:@hash)[:R]).to eq([["cv", "progress"]])
     end
 
     context "when updating a Tap other than the core Tap" do
@@ -102,7 +102,7 @@ RSpec.describe Homebrew::Cmd::UpdateReport do
 
         expect(hub.select_formula_or_cask(:A)).to be_empty
         expect(hub.select_formula_or_cask(:D)).to be_empty
-        expect(hub.select_formula_or_cask(:R)).to be_empty
+        expect(hub.instance_variable_get(:@hash)[:R]).to be_nil
       end
 
       specify "with renamed Formula and restructured Tap" do
@@ -111,7 +111,7 @@ RSpec.describe Homebrew::Cmd::UpdateReport do
 
         expect(hub.select_formula_or_cask(:A)).to be_empty
         expect(hub.select_formula_or_cask(:D)).to be_empty
-        expect(hub.select_formula_or_cask(:R)).to eq([%w[foo/bar/xchat foo/bar/xchat2]])
+        expect(hub.instance_variable_get(:@hash)[:R]).to eq([%w[foo/bar/xchat foo/bar/xchat2]])
       end
 
       specify "with simulated 'homebrew/php' restructuring" do
@@ -119,7 +119,7 @@ RSpec.describe Homebrew::Cmd::UpdateReport do
 
         expect(hub.select_formula_or_cask(:A)).to be_empty
         expect(hub.select_formula_or_cask(:D)).to be_empty
-        expect(hub.select_formula_or_cask(:R)).to be_empty
+        expect(hub.instance_variable_get(:@hash)[:R]).to be_nil
       end
 
       specify "with Formula changes" do
@@ -127,7 +127,7 @@ RSpec.describe Homebrew::Cmd::UpdateReport do
 
         expect(hub.select_formula_or_cask(:A)).to eq(%w[foo/bar/lua])
         expect(hub.select_formula_or_cask(:M)).to eq(%w[foo/bar/git])
-        expect(hub.select_formula_or_cask(:D)).to be_empty
+        expect(hub.instance_variable_get(:@hash)[:R]).to be_nil
       end
     end
   end
diff --git a/Library/Homebrew/test/download_strategies/curl_spec.rb b/Library/Homebrew/test/download_strategies/curl_spec.rb
index a7c5deee52..c3da1134c9 100644
--- a/Library/Homebrew/test/download_strategies/curl_spec.rb
+++ b/Library/Homebrew/test/download_strategies/curl_spec.rb
@@ -173,7 +173,7 @@ RSpec.describe CurlDownloadStrategy do
               hash_including(args: array_including_cons("#{artifact_domain}/#{resource_path}")),
             )
             .at_least(:once)
-            .and_return(SystemCommand::Result.new(["curl"], [""], status, secrets: []))
+            .and_return(SystemCommand::Result.new(["curl"], [[:stdout, ""]], status, secrets: []))
 
           strategy.fetch
         end
@@ -191,7 +191,7 @@ RSpec.describe CurlDownloadStrategy do
               hash_including(args: array_including_cons("#{artifact_domain}/#{resource_path}")),
             )
             .at_least(:once)
-            .and_return(SystemCommand::Result.new(["curl"], [""], status, secrets: []))
+            .and_return(SystemCommand::Result.new(["curl"], [[:stdout, ""]], status, secrets: []))
 
           strategy.fetch
         end
diff --git a/Library/Homebrew/test/livecheck/strategy/header_match_spec.rb b/Library/Homebrew/test/livecheck/strategy/header_match_spec.rb
index 39553a28d0..aa9b2d7c46 100644
--- a/Library/Homebrew/test/livecheck/strategy/header_match_spec.rb
+++ b/Library/Homebrew/test/livecheck/strategy/header_match_spec.rb
@@ -110,7 +110,7 @@ RSpec.describe Homebrew::Livecheck::Strategy::HeaderMatch do
 
     it "errors on an invalid return type from a block" do
       expect { header_match.versions_from_headers(headers) { 123 } }
-        .to raise_error(TypeError, Homebrew::Livecheck::Strategy::INVALID_BLOCK_RETURN_VALUE_MSG)
+        .to raise_error(TypeError, /Parameter 'headers': Expected type T::Hash\[String, String\]/o)
     end
   end
 end
diff --git a/Library/Homebrew/test/services/cli_spec.rb b/Library/Homebrew/test/services/cli_spec.rb
index c8cbc717c2..006f8a8adc 100644
--- a/Library/Homebrew/test/services/cli_spec.rb
+++ b/Library/Homebrew/test/services/cli_spec.rb
@@ -87,8 +87,9 @@ RSpec.describe Homebrew::Services::Cli do
   describe "#run" do
     it "checks missing file causes error" do
       expect(Homebrew::Services::System).not_to receive(:root?)
+      service = instance_double(Homebrew::Services::FormulaWrapper, name: "service_name")
       expect do
-        services_cli.start(["service_name"], "/non/existent/path")
+        services_cli.start([service], "/non/existent/path")
       end.to raise_error(UsageError, "Invalid usage: Provided service file does not exist.")
     end
 
@@ -110,8 +111,9 @@ RSpec.describe Homebrew::Services::Cli do
   describe "#start" do
     it "checks missing file causes error" do
       expect(Homebrew::Services::System).not_to receive(:root?)
+      service = instance_double(Homebrew::Services::FormulaWrapper, name: "service_name")
       expect do
-        services_cli.start(["service_name"], "/hfdkjshksdjhfkjsdhf/fdsjghsdkjhb")
+        services_cli.start([service], "/hfdkjshksdjhfkjsdhf/fdsjghsdkjhb")
       end.to raise_error(UsageError, "Invalid usage: Provided service file does not exist.")
     end
 
diff --git a/Library/Homebrew/test/services/commands/info_spec.rb b/Library/Homebrew/test/services/commands/info_spec.rb
index 8b5c5cefee..788f229299 100644
--- a/Library/Homebrew/test/services/commands/info_spec.rb
+++ b/Library/Homebrew/test/services/commands/info_spec.rb
@@ -23,7 +23,7 @@ RSpec.describe Homebrew::Services::Commands::Info do
 
     it "succeeds with items" do
       out = "service ()\nRunning: true\nLoaded: true\nSchedulable: false\n"
-      formula = {
+      formula_wrapper = instance_double(Homebrew::Services::FormulaWrapper, to_hash: {
         name:        "service",
         user:        "user",
         status:      :started,
@@ -31,9 +31,9 @@ RSpec.describe Homebrew::Services::Commands::Info do
         running:     true,
         loaded:      true,
         schedulable: false,
-      }
+      })
       expect do
-        described_class.run([formula], verbose: false, json: false)
+        described_class.run([formula_wrapper], verbose: false, json: false)
       end.to output(out).to_stdout
     end
 
@@ -48,8 +48,9 @@ RSpec.describe Homebrew::Services::Commands::Info do
         schedulable: false,
       }
       out = "#{JSON.pretty_generate([formula])}\n"
+      formula_wrapper = instance_double(Homebrew::Services::FormulaWrapper, to_hash: formula)
       expect do
-        described_class.run([formula], verbose: false, json: true)
+        described_class.run([formula_wrapper], verbose: false, json: true)
       end.to output(out).to_stdout
     end
   end
diff --git a/Library/Homebrew/test/system_command_spec.rb b/Library/Homebrew/test/system_command_spec.rb
index 7eefe508fa..1884f39049 100644
--- a/Library/Homebrew/test/system_command_spec.rb
+++ b/Library/Homebrew/test/system_command_spec.rb
@@ -275,7 +275,7 @@ RSpec.describe SystemCommand do
 
       FileUtils.chmod "+x", path/"tool"
 
-      expect(described_class.run("tool", env: { "PATH" => path }).stdout).to include "Hello, world!"
+      expect(described_class.run("tool", env: { "PATH" => path.to_s }).stdout).to include "Hello, world!"
     end
   end
 
diff --git a/Library/Homebrew/test/tab_spec.rb b/Library/Homebrew/test/tab_spec.rb
index 594e9c7747..c3dc4a1a23 100644
--- a/Library/Homebrew/test/tab_spec.rb
+++ b/Library/Homebrew/test/tab_spec.rb
@@ -241,7 +241,7 @@ RSpec.describe Tab do
       tab = described_class.from_file(path)
       source_path = "/usr/local/Library/Taps/homebrew/homebrew-core/Formula/foo.rb"
       runtime_dependencies = [{ "full_name" => "foo", "version" => "1.0" }]
-      changed_files = %w[INSTALL_RECEIPT.json bin/foo]
+      changed_files = %w[INSTALL_RECEIPT.json bin/foo].map { Pathname.new(_1) }
 
       expect(tab.used_options.sort).to eq(used_options.sort)
       expect(tab.unused_options.sort).to eq(unused_options.sort)
@@ -271,7 +271,7 @@ RSpec.describe Tab do
       tab = described_class.from_file_content(path.read, path)
       source_path = "/usr/local/Library/Taps/homebrew/homebrew-core/Formula/foo.rb"
       runtime_dependencies = [{ "full_name" => "foo", "version" => "1.0" }]
-      changed_files = %w[INSTALL_RECEIPT.json bin/foo]
+      changed_files = %w[INSTALL_RECEIPT.json bin/foo].map { Pathname.new(_1) }
 
       expect(tab.used_options.sort).to eq(used_options.sort)
       expect(tab.unused_options.sort).to eq(unused_options.sort)
diff --git a/Library/Homebrew/test/utils/analytics_spec.rb b/Library/Homebrew/test/utils/analytics_spec.rb
index 4428b1423a..c221af0d6f 100644
--- a/Library/Homebrew/test/utils/analytics_spec.rb
+++ b/Library/Homebrew/test/utils/analytics_spec.rb
@@ -184,7 +184,7 @@ RSpec.describe Utils::Analytics do
   end
 
   specify "::table_output" do
-    results = { ack: 10, wget: 100 }
+    results = { "ack" => 10, "wget" => 100 }
     expect { described_class.table_output("install", "30", results) }
       .to output(/110 |  100.00%/).to_stdout
       .and not_to_output.to_stderr
diff --git a/Library/Homebrew/test/utils/inreplace_spec.rb b/Library/Homebrew/test/utils/inreplace_spec.rb
index 3014f1b789..05951ae3fa 100644
--- a/Library/Homebrew/test/utils/inreplace_spec.rb
+++ b/Library/Homebrew/test/utils/inreplace_spec.rb
@@ -86,7 +86,7 @@ RSpec.describe Utils::Inreplace do
     it "raises error if there is no old value" do
       expect do
         described_class.inreplace_pairs(file.path, [[nil, "f"]])
-      end.to raise_error(Utils::Inreplace::Error)
+      end.to raise_error(TypeError)
     end
 
     it "substitutes returned string but not file when `read_only_run: true`" do
diff --git a/Library/Homebrew/unpack_strategy/zip.rb b/Library/Homebrew/unpack_strategy/zip.rb
index 28e413e00a..cbc39ba3f2 100644
--- a/Library/Homebrew/unpack_strategy/zip.rb
+++ b/Library/Homebrew/unpack_strategy/zip.rb
@@ -36,7 +36,7 @@ module UnpackStrategy
         quiet_flags = verbose ? [] : ["-qq"]
         result = system_command! "unzip",
                                  args:         [*quiet_flags, "-o", path, "-d", unpack_dir],
-                                 env:          { "PATH" => PATH.new(unzip&.opt_bin, ENV.fetch("PATH")) },
+                                 env:          { "PATH" => PATH.new(unzip&.opt_bin, ENV.fetch("PATH")).to_s },
                                  verbose:,
                                  print_stderr: false
 
diff --git a/Library/Homebrew/utils/analytics.rb b/Library/Homebrew/utils/analytics.rb
index d9136a168c..2ac747df12 100644
--- a/Library/Homebrew/utils/analytics.rb
+++ b/Library/Homebrew/utils/analytics.rb
@@ -360,7 +360,7 @@ module Utils
         nil
       end
 
-      sig { returns(T::Hash[Symbol, String]) }
+      sig { returns(T::Hash[Symbol, T.any(T::Boolean, String)]) }
       def default_package_tags
         cache[:default_package_tags] ||= begin
           # Only display default prefixes to reduce cardinality and improve privacy