diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index a0cdf8b74a644..2c691fad81b3f 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -134,11 +134,12 @@ def install
       raise
     end
 
+    sig { void }
     def check_deprecate_disable
       deprecate_disable_type = DeprecateDisable.type(@cask)
       return if deprecate_disable_type.nil?
 
-      message = DeprecateDisable.message(@cask)
+      message = DeprecateDisable.message(@cask).to_s
       message_full = "#{@cask.token} has been #{message}"
 
       case deprecate_disable_type
diff --git a/Library/Homebrew/deprecate_disable.rb b/Library/Homebrew/deprecate_disable.rb
index e6ed2ef2c8e07..05e85ec8edae2 100644
--- a/Library/Homebrew/deprecate_disable.rb
+++ b/Library/Homebrew/deprecate_disable.rb
@@ -1,4 +1,4 @@
-# typed: true # rubocop:todo Sorbet/StrictSigil
+# typed: strict
 # frozen_string_literal: true
 
 # Helper module for handling `disable!` and `deprecate!`.
@@ -6,7 +6,7 @@
 module DeprecateDisable
   module_function
 
-  FORMULA_DEPRECATE_DISABLE_REASONS = {
+  FORMULA_DEPRECATE_DISABLE_REASONS = T.let({
     does_not_build:      "does not build",
     no_license:          "has no license",
     repo_archived:       "has an archived upstream repository",
@@ -19,27 +19,29 @@ module DeprecateDisable
                          "a different checksum than the current one. " \
                          "Upstream's repository might have been compromised. " \
                          "We can re-package this once upstream has confirmed that they retagged their release",
-  }.freeze
+  }.freeze, T::Hash[Symbol, String])
 
-  CASK_DEPRECATE_DISABLE_REASONS = {
+  CASK_DEPRECATE_DISABLE_REASONS = T.let({
     discontinued:             "is discontinued upstream",
     moved_to_mas:             "is now exclusively distributed on the Mac App Store",
     no_longer_available:      "is no longer available upstream",
     no_longer_meets_criteria: "no longer meets the criteria for acceptable casks",
     unmaintained:             "is not maintained upstream",
     unsigned:                 "is unsigned or does not meet signature requirements",
-  }.freeze
+  }.freeze, T::Hash[Symbol, String])
 
   # One year when << or >> to Date.today.
   REMOVE_DISABLED_TIME_WINDOW = 12
-  REMOVE_DISABLED_BEFORE = (Date.today << REMOVE_DISABLED_TIME_WINDOW).freeze
+  REMOVE_DISABLED_BEFORE = T.let((Date.today << REMOVE_DISABLED_TIME_WINDOW).freeze, Date)
 
+  sig { params(formula_or_cask: T.any(Formula, Cask::Cask)).returns(T.nilable(Symbol)) }
   def type(formula_or_cask)
     return :deprecated if formula_or_cask.deprecated?
 
     :disabled if formula_or_cask.disabled?
   end
 
+  sig { params(formula_or_cask: T.any(Formula, Cask::Cask)).returns(T.nilable(String)) }
   def message(formula_or_cask)
     return if type(formula_or_cask).blank?
 
@@ -92,9 +94,12 @@ def message(formula_or_cask)
     message
   end
 
+  sig { params(string: T.nilable(String), type: Symbol).returns(T.nilable(T.any(String, Symbol))) }
   def to_reason_string_or_symbol(string, type:)
-    if (type == :formula && FORMULA_DEPRECATE_DISABLE_REASONS.key?(string&.to_sym)) ||
-       (type == :cask && CASK_DEPRECATE_DISABLE_REASONS.key?(string&.to_sym))
+    return if string.nil?
+
+    if (type == :formula && FORMULA_DEPRECATE_DISABLE_REASONS.key?(string.to_sym)) ||
+       (type == :cask && CASK_DEPRECATE_DISABLE_REASONS.key?(string.to_sym))
       return string.to_sym
     end
 
diff --git a/Library/Homebrew/test/deprecate_disable_spec.rb b/Library/Homebrew/test/deprecate_disable_spec.rb
index ce0be52578de8..71ed29e2b3192 100644
--- a/Library/Homebrew/test/deprecate_disable_spec.rb
+++ b/Library/Homebrew/test/deprecate_disable_spec.rb
@@ -3,14 +3,24 @@
 require "deprecate_disable"
 
 RSpec.describe DeprecateDisable do
+  let(:deprecate_date) { Date.parse("2020-01-01") }
+  let(:disable_date) { deprecate_date >> DeprecateDisable::REMOVE_DISABLED_TIME_WINDOW }
   let(:deprecated_formula) do
     instance_double(Formula, deprecated?: true, disabled?: false, deprecation_reason: :does_not_build,
                     deprecation_replacement: nil, deprecation_date: nil, disable_date: nil)
   end
+  let(:deprecated_formula_with_date) do
+    instance_double(Formula, deprecated?: true, disabled?: false, deprecation_reason: :does_not_build,
+                    deprecation_replacement: nil, deprecation_date: deprecate_date, disable_date: nil)
+  end
   let(:disabled_formula) do
     instance_double(Formula, deprecated?: false, disabled?: true, disable_reason: "is broken",
                     disable_replacement: nil, deprecation_date: nil, disable_date: nil)
   end
+  let(:disabled_formula_with_date) do
+    instance_double(Formula, deprecated?: false, disabled?: true, disable_reason: :does_not_build,
+                    disable_replacement: nil, deprecation_date: nil, disable_date: disable_date)
+  end
   let(:deprecated_cask) do
     instance_double(Cask::Cask, deprecated?: true, disabled?: false, deprecation_reason: :discontinued,
                    deprecation_replacement: nil, deprecation_date: nil, disable_date: nil)
@@ -39,7 +49,9 @@
   before do
     formulae = [
       deprecated_formula,
+      deprecated_formula_with_date,
       disabled_formula,
+      disabled_formula_with_date,
       deprecated_formula_with_replacement,
       disabled_formula_with_replacement,
     ]
@@ -86,11 +98,22 @@
         .to eq "deprecated because it does not build!"
     end
 
+    it "returns a deprecation message with disable date" do
+      allow(Date).to receive(:today).and_return(deprecate_date + 1)
+      expect(described_class.message(deprecated_formula_with_date))
+        .to eq "deprecated because it does not build! It will be disabled on #{disable_date}."
+    end
+
     it "returns a disable message with a custom reason" do
       expect(described_class.message(disabled_formula))
         .to eq "disabled because it is broken!"
     end
 
+    it "returns a disable message with disable date" do
+      expect(described_class.message(disabled_formula_with_date))
+        .to eq "disabled because it does not build! It was disabled on #{disable_date}."
+    end
+
     it "returns a deprecation message with a preset cask reason" do
       expect(described_class.message(deprecated_cask))
         .to eq "deprecated because it is discontinued upstream!"