diff --git a/Library/Homebrew/cask/cmd/install.rb b/Library/Homebrew/cask/cmd/install.rb
index 428e58024a..04c1869b74 100644
--- a/Library/Homebrew/cask/cmd/install.rb
+++ b/Library/Homebrew/cask/cmd/install.rb
@@ -13,6 +13,10 @@ module Cask
         [:switch, "--skip-cask-deps", {
           description: "Skip installing cask dependencies.",
         }],
+        [:switch, "--zap", {
+          description: "For use with `brew reinstall --cask`. Remove all files associated with a cask. " \
+                       "*May remove files which are shared between applications.*",
+        }],
       ].freeze
 
       def self.parser(&block)
@@ -39,6 +43,7 @@ module Cask
           require_sha:    args.require_sha?,
           quarantine:     args.quarantine?,
           quiet:          args.quiet?,
+          zap:            args.zap?,
         )
       end
 
@@ -50,7 +55,8 @@ module Cask
         skip_cask_deps: nil,
         require_sha: nil,
         quarantine: nil,
-        quiet: nil
+        quiet: nil,
+        zap: nil
       )
         odie "Installing casks is supported only on macOS" unless OS.mac?
 
@@ -61,6 +67,7 @@ module Cask
           skip_cask_deps: skip_cask_deps,
           require_sha:    require_sha,
           quarantine:     quarantine,
+          zap:            zap,
         }.compact
 
         options[:quarantine] = true if options[:quarantine].nil?
diff --git a/Library/Homebrew/cask/cmd/reinstall.rb b/Library/Homebrew/cask/cmd/reinstall.rb
index 1470bffede..9637805450 100644
--- a/Library/Homebrew/cask/cmd/reinstall.rb
+++ b/Library/Homebrew/cask/cmd/reinstall.rb
@@ -19,6 +19,7 @@ module Cask
           skip_cask_deps: args.skip_cask_deps?,
           require_sha:    args.require_sha?,
           quarantine:     args.quarantine?,
+          zap:            args.zap?,
         )
       end
 
@@ -29,7 +30,8 @@ module Cask
         skip_cask_deps: nil,
         binaries: nil,
         require_sha: nil,
-        quarantine: nil
+        quarantine: nil,
+        zap: nil
       )
         require "cask/installer"
 
@@ -40,6 +42,7 @@ module Cask
           skip_cask_deps: skip_cask_deps,
           require_sha:    require_sha,
           quarantine:     quarantine,
+          zap:            zap,
         }.compact
 
         options[:quarantine] = true if options[:quarantine].nil?
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index 4661310777..c389d17939 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -29,7 +29,7 @@ module Cask
 
     def initialize(cask, command: SystemCommand, force: false,
                    skip_cask_deps: false, binaries: true, verbose: false,
-                   require_sha: false, upgrade: false,
+                   zap: false, require_sha: false, upgrade: false,
                    installed_as_dependency: false, quarantine: true,
                    verify_download_integrity: true, quiet: false)
       @cask = cask
@@ -38,6 +38,7 @@ module Cask
       @skip_cask_deps = skip_cask_deps
       @binaries = binaries
       @verbose = verbose
+      @zap = zap
       @require_sha = require_sha
       @reinstall = false
       @upgrade = upgrade
@@ -48,7 +49,7 @@ module Cask
     end
 
     attr_predicate :binaries?, :force?, :skip_cask_deps?, :require_sha?,
-                   :reinstall?, :upgrade?, :verbose?, :installed_as_dependency?,
+                   :reinstall?, :upgrade?, :verbose?, :zap?, :installed_as_dependency?,
                    :quarantine?, :quiet?
 
     def self.caveats(cask)
@@ -157,7 +158,8 @@ module Cask
       installed_cask = installed_caskfile.exist? ? CaskLoader.load(installed_caskfile) : @cask
 
       # Always force uninstallation, ignore method parameter
-      Installer.new(installed_cask, verbose: verbose?, force: true, upgrade: upgrade?).uninstall
+      cask_installer = Installer.new(installed_cask, verbose: verbose?, force: true, upgrade: upgrade?)
+      zap? ? cask_installer.zap : cask_installer.uninstall
     end
 
     sig { returns(String) }
diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index 9bceda66b2..e4b692afab 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -159,6 +159,7 @@ module Homebrew
         require_sha:    args.require_sha?,
         skip_cask_deps: args.skip_cask_deps?,
         quarantine:     args.quarantine?,
+        zap:            args.zap?,
       )
     end
 
diff --git a/Library/Homebrew/test/cask/cmd/list_spec.rb b/Library/Homebrew/test/cask/cmd/list_spec.rb
index ca7be9d1c9..81f7a83c8e 100644
--- a/Library/Homebrew/test/cask/cmd/list_spec.rb
+++ b/Library/Homebrew/test/cask/cmd/list_spec.rb
@@ -108,7 +108,12 @@ describe Cask::Cmd::List, :cask do
             "artifacts": [
               [
                 "Caffeine.app"
-              ]
+              ],
+              {
+                "trash": "$HOME/support/fixtures/cask/caffeine/org.example.caffeine.plist",
+                "signal": {
+                }
+              }
             ],
             "caveats": null,
             "depends_on": {
diff --git a/Library/Homebrew/test/cask/cmd/reinstall_spec.rb b/Library/Homebrew/test/cask/cmd/reinstall_spec.rb
index 013b90b7cc..723d767b17 100644
--- a/Library/Homebrew/test/cask/cmd/reinstall_spec.rb
+++ b/Library/Homebrew/test/cask/cmd/reinstall_spec.rb
@@ -24,6 +24,31 @@ describe Cask::Cmd::Reinstall, :cask do
     }.to output(output).to_stdout
   end
 
+  it "displays the reinstallation progress with zapping" do
+    caffeine = Cask::CaskLoader.load(cask_path("local-caffeine"))
+
+    Cask::Installer.new(caffeine).install
+
+    output = Regexp.new <<~EOS
+      ==> Downloading file:.*caffeine.zip
+      Already downloaded: .*--caffeine.zip
+      ==> Implied `brew uninstall --cask local-caffeine`
+      ==> Backing App 'Caffeine.app' up to '.*Caffeine.app'
+      ==> Removing App '.*Caffeine.app'
+      ==> Dispatching zap stanza
+      ==> Trashing files:
+      .*org\.example\.caffeine\.plist
+      ==> Removing all staged versions of Cask 'local-caffeine'
+      ==> Installing Cask local-caffeine
+      ==> Moving App 'Caffeine.app' to '.*Caffeine.app'
+      .*local-caffeine was successfully installed!
+    EOS
+
+    expect {
+      described_class.run("local-caffeine", "--zap")
+    }.to output(output).to_stdout
+  end
+
   it "allows reinstalling a Cask" do
     Cask::Cmd::Install.run("local-transmission")
 
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/local-caffeine.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/local-caffeine.rb
index c467ca45ac..4a1c3d54fb 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/local-caffeine.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/local-caffeine.rb
@@ -6,4 +6,6 @@ cask "local-caffeine" do
   homepage "https://brew.sh/"
 
   app "Caffeine.app"
+
+  zap trash: "#{TEST_FIXTURE_DIR}/cask/caffeine/org.example.caffeine.plist"
 end