diff --git a/Library/Homebrew/cask/cask_loader.rb b/Library/Homebrew/cask/cask_loader.rb
index 22b7efe25e..93332576ba 100644
--- a/Library/Homebrew/cask/cask_loader.rb
+++ b/Library/Homebrew/cask/cask_loader.rb
@@ -286,6 +286,16 @@ module Cask
           desc json_cask[:desc]
           homepage json_cask[:homepage]
 
+          if (deprecation_date = json_cask[:deprecation_date].presence)
+            reason = DeprecateDisable.to_reason_string_or_symbol json_cask[:deprecation_reason], type: :cask
+            deprecate! date: deprecation_date, because: reason
+          end
+
+          if (disable_date = json_cask[:disable_date].presence)
+            reason = DeprecateDisable.to_reason_string_or_symbol json_cask[:disable_reason], type: :cask
+            deprecate! date: disable_date, because: reason
+          end
+
           auto_updates json_cask[:auto_updates] unless json_cask[:auto_updates].nil?
           conflicts_with(**json_cask[:conflicts_with]) if json_cask[:conflicts_with].present?
 
diff --git a/Library/Homebrew/cask/exceptions.rb b/Library/Homebrew/cask/exceptions.rb
index 05bdde818a..acbc0fa338 100644
--- a/Library/Homebrew/cask/exceptions.rb
+++ b/Library/Homebrew/cask/exceptions.rb
@@ -54,6 +54,23 @@ module Cask
     end
   end
 
+  # Error when a cask cannot be installed.
+  #
+  # @api private
+  class CaskCannotBeInstalledError < AbstractCaskErrorWithToken
+    attr_reader :message
+
+    def initialize(token, message)
+      super(token)
+      @message = message
+    end
+
+    sig { returns(String) }
+    def to_s
+      "Cask '#{token}' has been #{message}"
+    end
+  end
+
   # Error when a cask conflicts with another cask.
   #
   # @api private
diff --git a/Library/Homebrew/cask/info.rb b/Library/Homebrew/cask/info.rb
index 64caa572a7..e80a88024a 100644
--- a/Library/Homebrew/cask/info.rb
+++ b/Library/Homebrew/cask/info.rb
@@ -12,6 +12,8 @@ module Cask
 
       output = +"#{title_info(cask)}\n"
       output << "#{Formatter.url(cask.homepage)}\n" if cask.homepage
+      deprecate_disable = DeprecateDisable.message(cask)
+      output << "#{deprecate_disable.capitalize}\n" if deprecate_disable
       output << installation_info(cask)
       repo = repo_info(cask)
       output << "#{repo}\n" if repo
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index a9e42cc6b3..45383d30ec 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -93,6 +93,7 @@ module Cask
       old_config = @cask.config
       predecessor = @cask if reinstall? && @cask.installed?
 
+      check_deprecate_disable
       check_conflicts
 
       print caveats
@@ -124,6 +125,17 @@ on_request: true)
       raise
     end
 
+    def check_deprecate_disable
+      deprecate_disable_type = DeprecateDisable.type(@cask)
+      return if deprecate_disable_type.blank?
+
+      if deprecate_disable_type == :deprecated
+        opoo "#{@cask.token} has been #{DeprecateDisable.message(@cask)}"
+      elsif deprecate_disable_type == :disabled
+        raise CaskCannotBeInstalledError.new(@cask, DeprecateDisable.message(@cask))
+      end
+    end
+
     def check_conflicts
       return unless @cask.conflicts_with
 
diff --git a/Library/Homebrew/cmd/info.rb b/Library/Homebrew/cmd/info.rb
index ca7ac0f28b..705790a8b3 100644
--- a/Library/Homebrew/cmd/info.rb
+++ b/Library/Homebrew/cmd/info.rb
@@ -278,14 +278,8 @@ module Homebrew
     puts formula.desc if formula.desc
     puts Formatter.url(formula.homepage) if formula.homepage
 
-    deprecate_disable_type, deprecate_disable_reason = DeprecateDisable.deprecate_disable_info formula
-    if deprecate_disable_type.present?
-      if deprecate_disable_reason.present?
-        puts "#{deprecate_disable_type.capitalize} because it #{deprecate_disable_reason}!"
-      else
-        puts "#{deprecate_disable_type.capitalize}!"
-      end
-    end
+    deprecate_disable_info_string = DeprecateDisable.message(formula)
+    puts deprecate_disable_info_string.capitalize if deprecate_disable_info_string.present?
 
     conflicts = formula.conflicts.map do |conflict|
       reason = " (because #{conflict.reason})" if conflict.reason
diff --git a/Library/Homebrew/deprecate_disable.rb b/Library/Homebrew/deprecate_disable.rb
index b64e98e854..8ade837dea 100644
--- a/Library/Homebrew/deprecate_disable.rb
+++ b/Library/Homebrew/deprecate_disable.rb
@@ -35,23 +35,39 @@ module DeprecateDisable
     **SHARED_DEPRECATE_DISABLE_REASONS,
   }.freeze
 
-  def deprecate_disable_info(formula_or_cask)
-    if formula_or_cask.deprecated?
-      type = :deprecated
-      reason = formula_or_cask.deprecation_reason
+  def type(formula_or_cask)
+    return :deprecated if formula_or_cask.deprecated?
+    return :disabled if formula_or_cask.disabled?
+  end
+
+  def message(formula_or_cask)
+    return if type(formula_or_cask).blank?
+
+    reason = if formula_or_cask.deprecated?
+      formula_or_cask.deprecation_reason
     elsif formula_or_cask.disabled?
-      type = :disabled
-      reason = formula_or_cask.disable_reason
-    else
-      return
+      formula_or_cask.disable_reason
     end
 
     reason = if formula_or_cask.is_a?(Formula) && FORMULA_DEPRECATE_DISABLE_REASONS.key?(reason)
       FORMULA_DEPRECATE_DISABLE_REASONS[reason]
     elsif formula_or_cask.is_a?(Cask::Cask) && CASK_DEPRECATE_DISABLE_REASONS.key?(reason)
       CASK_DEPRECATE_DISABLE_REASONS[reason]
+    else
+      reason
     end
 
-    [type, reason]
+    return "#{type(formula_or_cask)} because it #{reason}!" if reason.present?
+
+    "#{type(formula_or_cask)}!"
+  end
+
+  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 string.to_sym
+    end
+
+    string
   end
 end
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index 512f475b77..f0bec7ee80 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -642,6 +642,18 @@ module Homebrew
         EOS
       end
 
+      def check_cask_deprecated_disabled
+        deprecated_or_disabled = Cask::Caskroom.casks.select(&:deprecated?)
+        deprecated_or_disabled += Cask::Caskroom.casks.select(&:disabled?)
+        return if deprecated_or_disabled.empty?
+
+        <<~EOS
+          Some installed casks are deprecated or disabled.
+          You should find replacements for the following casks:
+            #{deprecated_or_disabled.sort_by(&:token).uniq * "\n  "}
+        EOS
+      end
+
       sig { returns(T.nilable(String)) }
       def check_git_status
         return unless Utils::Git.available?
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index ce55a97d9d..9b46b15d02 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -200,21 +200,14 @@ class FormulaInstaller
 
   sig { void }
   def prelude
-    type, reason = DeprecateDisable.deprecate_disable_info formula
-    if type.present?
-      case type
-      when :deprecated
-        if reason.present?
-          opoo "#{formula.full_name} has been deprecated because it #{reason}!"
-        else
-          opoo "#{formula.full_name} has been deprecated!"
-        end
-      when :disabled
-        if reason.present?
-          raise CannotInstallFormulaError, "#{formula.full_name} has been disabled because it #{reason}!"
-        end
+    deprecate_disable_type = DeprecateDisable.type(formula)
+    if deprecate_disable_type.present?
+      message = "#{formula.full_name} has been #{DeprecateDisable.message(formula)}"
 
-        raise CannotInstallFormulaError, "#{formula.full_name} has been disabled!"
+      if deprecate_disable_type == :deprecated
+        opoo message
+      elsif deprecate_disable_type == :disabled
+        raise CannotInstallFormulaError, message
       end
     end
 
diff --git a/Library/Homebrew/formulary.rb b/Library/Homebrew/formulary.rb
index 5d6e47c5b0..90857aa3b9 100644
--- a/Library/Homebrew/formulary.rb
+++ b/Library/Homebrew/formulary.rb
@@ -7,6 +7,7 @@ require "tab"
 require "utils/bottles"
 require "service"
 require "utils/curl"
+require "deprecate_disable"
 
 require "active_support/core_ext/hash/deep_transform_values"
 
@@ -301,12 +302,12 @@ module Formulary
       end
 
       if (deprecation_date = json_formula["deprecation_date"].presence)
-        reason = Formulary.convert_to_deprecate_disable_reason_string_or_symbol json_formula["deprecation_reason"]
+        reason = DeprecateDisable.to_reason_string_or_symbol json_formula["deprecation_reason"], type: :formula
         deprecate! date: deprecation_date, because: reason
       end
 
       if (disable_date = json_formula["disable_date"].presence)
-        reason = Formulary.convert_to_deprecate_disable_reason_string_or_symbol json_formula["disable_reason"]
+        reason = DeprecateDisable.to_reason_string_or_symbol json_formula["disable_reason"], type: :formula
         disable! date: disable_date, because: reason
       end
 
@@ -462,13 +463,6 @@ module Formulary
     string
   end
 
-  def self.convert_to_deprecate_disable_reason_string_or_symbol(string)
-    require "deprecate_disable"
-    return string unless DeprecateDisable::FORMULARY_DEPRECATE_DISABLE_REASONS.keys.map(&:to_s).include?(string)
-
-    string.to_sym
-  end
-
   # A {FormulaLoader} returns instances of formulae.
   # Subclasses implement loaders for particular sources of formulae.
   class FormulaLoader