diff --git a/Library/Homebrew/cask/info.rb b/Library/Homebrew/cask/info.rb
index 3463f6ced8..64caa572a7 100644
--- a/Library/Homebrew/cask/info.rb
+++ b/Library/Homebrew/cask/info.rb
@@ -78,7 +78,7 @@ module Cask
       url = if cask.tap.custom_remote? && !cask.tap.remote.nil?
         cask.tap.remote
       else
-        "#{cask.tap.default_remote}/blob/HEAD/Casks/#{cask.token}.rb"
+        "#{cask.tap.default_remote}/blob/HEAD/#{cask.tap.relative_cask_path(cask.token)}"
       end
 
       "From: #{Formatter.url(url)}"
diff --git a/Library/Homebrew/cmd/info.rb b/Library/Homebrew/cmd/info.rb
index afa6f03c3d..1898204080 100644
--- a/Library/Homebrew/cmd/info.rb
+++ b/Library/Homebrew/cmd/info.rb
@@ -241,18 +241,23 @@ module Homebrew
     end
   end
 
-  def github_info(formula)
-    return formula.path if formula.tap.blank? || formula.tap.remote.blank?
+  def github_info(formula_or_cask)
+    return formula_or_cask.path if formula_or_cask.tap.blank? || formula_or_cask.tap.remote.blank?
 
-    path = case formula
+    path = case formula_or_cask
     when Formula
+      formula = formula_or_cask
       formula.path.relative_path_from(T.must(formula.tap).path)
     when Cask::Cask
-      return "#{formula.tap.default_remote}/blob/HEAD/Casks/#{formula.token}.rb" if formula.sourcefile_path.blank?
+      cask = formula_or_cask
+      if cask.sourcefile_path.blank?
+        return "#{cask.tap.default_remote}/blob/HEAD/#{cask.tap.relative_cask_path(cask.token)}"
+      end
 
-      formula.sourcefile_path.relative_path_from(formula.tap.path)
+      cask.sourcefile_path.relative_path_from(cask.tap.path)
     end
-    github_remote_path(formula.tap.remote, path)
+
+    github_remote_path(formula_or_cask.tap.remote, path)
   end
 
   def info_formula(formula, args:)
diff --git a/Library/Homebrew/tap.rb b/Library/Homebrew/tap.rb
index 57325f50b7..a5fc3d8527 100644
--- a/Library/Homebrew/tap.rb
+++ b/Library/Homebrew/tap.rb
@@ -516,6 +516,12 @@ class Tap
     cask_dir/"#{token.downcase}.rb"
   end
 
+  sig { params(token: String).returns(String) }
+  def relative_cask_path(token)
+    new_cask_path(token).to_s
+                        .delete_prefix("#{path}/")
+  end
+
   def contents
     contents = []
 
@@ -563,9 +569,10 @@ class Tap
   sig { returns(T::Hash[String, Pathname]) }
   def formula_files_by_name
     formula_files.each_with_object({}) do |file, hash|
-      # If there's more than one file with the same basename: intentionally
-      # ignore the later ones here.
-      hash[file.basename(".rb").to_s] ||= file
+      # If there's more than one file with the same basename: use the longer one to prioritise more specifc results.
+      basename = file.basename(".rb").to_s
+      existing_file = hash[basename]
+      hash[basename] = file if existing_file.nil? || existing_file.to_s.length < file.to_s.length
     end
   end
 
@@ -592,9 +599,10 @@ class Tap
   sig { returns(T::Hash[String, Pathname]) }
   def cask_files_by_name
     cask_files.each_with_object({}) do |file, hash|
-      # If there's more than one file with the same basename: intentionally
-      # ignore the later ones here.
-      hash[file.basename(".rb").to_s] ||= file
+      # If there's more than one file with the same basename: use the longer one to prioritise more specifc results.
+      basename = file.basename(".rb").to_s
+      existing_file = hash[basename]
+      hash[basename] = file if existing_file.nil? || existing_file.to_s.length < file.to_s.length
     end
   end
 
@@ -1110,9 +1118,10 @@ class CoreTap < AbstractCoreTap
 
     Homebrew::API::Formula.all_formulae.each_with_object({}) do |item, hash|
       name, formula_hash = item
-      # If there's more than one file with the same basename: intentionally
-      # ignore the later ones here.
-      hash[name] ||= path/formula_hash["ruby_source_path"]
+      # If there's more than one item with the same path: use the longer one to prioritise more specific results.
+      existing_path = hash[name]
+      new_path = path/formula_hash["ruby_source_path"]
+      hash[name] = new_path if existing_path.nil? || existing_path.to_s.length < new_path.to_s.length
     end
   end
 end
@@ -1158,9 +1167,10 @@ class CoreCaskTap < AbstractCoreTap
 
     Homebrew::API::Cask.all_casks.each_with_object({}) do |item, hash|
       name, cask_hash = item
-      # If there's more than one file with the same basename: intentionally
-      # ignore the later ones here.
-      hash[name] ||= path/cask_hash["ruby_source_path"]
+      # If there's more than one item with the same path: use the longer one to prioritise more specific results.
+      existing_path = hash[name]
+      new_path = path/cask_hash["ruby_source_path"]
+      hash[name] = new_path if existing_path.nil? || existing_path.to_s.length < new_path.to_s.length
     end
   end
 
diff --git a/Library/Homebrew/test/cask/audit_spec.rb b/Library/Homebrew/test/cask/audit_spec.rb
index 5285b2517c..8048b1af18 100644
--- a/Library/Homebrew/test/cask/audit_spec.rb
+++ b/Library/Homebrew/test/cask/audit_spec.rb
@@ -531,37 +531,37 @@ describe Cask::Audit, :cask do
       end
 
       context "when the Cask is discontinued" do
-        let(:cask_token) { "livecheck/discontinued" }
+        let(:cask_token) { "livecheck/livecheck-discontinued" }
 
         it { is_expected.not_to error_with(message) }
       end
 
       context "when the Cask has a livecheck block referencing a discontinued Cask" do
-        let(:cask_token) { "livecheck/discontinued-reference" }
+        let(:cask_token) { "livecheck/livecheck-discontinued-reference" }
 
         it { is_expected.not_to error_with(message) }
       end
 
       context "when version is :latest" do
-        let(:cask_token) { "livecheck/version-latest" }
+        let(:cask_token) { "livecheck/livecheck-version-latest" }
 
         it { is_expected.not_to error_with(message) }
       end
 
       context "when the Cask has a livecheck block referencing a Cask where version is :latest" do
-        let(:cask_token) { "livecheck/version-latest-reference" }
+        let(:cask_token) { "livecheck/livecheck-version-latest-reference" }
 
         it { is_expected.not_to error_with(message) }
       end
 
       context "when url is unversioned" do
-        let(:cask_token) { "livecheck/url-unversioned" }
+        let(:cask_token) { "livecheck/livecheck-url-unversioned" }
 
         it { is_expected.not_to error_with(message) }
       end
 
       context "when the Cask has a livecheck block referencing a Cask with an unversioned url" do
-        let(:cask_token) { "livecheck/url-unversioned-reference" }
+        let(:cask_token) { "livecheck/livecheck-url-unversioned-reference" }
 
         it { is_expected.not_to error_with(message) }
       end
diff --git a/Library/Homebrew/test/cask/cask_spec.rb b/Library/Homebrew/test/cask/cask_spec.rb
index 10f69df402..71ce127d62 100644
--- a/Library/Homebrew/test/cask/cask_spec.rb
+++ b/Library/Homebrew/test/cask/cask_spec.rb
@@ -41,7 +41,7 @@ describe Cask::Cask, :cask do
     end
 
     it "returns an instance of the Cask from a JSON file" do
-      c = Cask::CaskLoader.load("#{tap_path}/caffeine.json")
+      c = Cask::CaskLoader.load("#{TEST_FIXTURE_DIR}/cask/caffeine.json")
       expect(c).to be_a(described_class)
       expect(c.token).to eq("caffeine")
     end
diff --git a/Library/Homebrew/test/cask/info_spec.rb b/Library/Homebrew/test/cask/info_spec.rb
index f17226ea6f..697e6e918b 100644
--- a/Library/Homebrew/test/cask/info_spec.rb
+++ b/Library/Homebrew/test/cask/info_spec.rb
@@ -10,7 +10,7 @@ describe Cask::Info, :cask do
       ==> local-transmission: 2.61
       https://transmissionbt.com/
       Not installed
-      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/local-transmission.rb
+      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/l/local-transmission.rb
       ==> Name
       Transmission
       ==> Description
@@ -27,7 +27,7 @@ describe Cask::Info, :cask do
       ==> with-auto-updates: 1.0 (auto_updates)
       https://brew.sh/autoupdates
       Not installed
-      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/with-auto-updates.rb
+      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/w/with-auto-updates.rb
       ==> Name
       AutoUpdates
       ==> Description
@@ -44,7 +44,7 @@ describe Cask::Info, :cask do
       ==> with-caveats: 1.2.3
       https://brew.sh/
       Not installed
-      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/with-caveats.rb
+      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/w/with-caveats.rb
       ==> Name
       None
       ==> Description
@@ -71,7 +71,7 @@ describe Cask::Info, :cask do
       ==> with-conditional-caveats: 1.2.3
       https://brew.sh/
       Not installed
-      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/with-conditional-caveats.rb
+      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/w/with-conditional-caveats.rb
       ==> Name
       None
       ==> Description
@@ -88,7 +88,7 @@ describe Cask::Info, :cask do
       ==> with-languages: 1.2.3
       https://brew.sh/
       Not installed
-      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/with-languages.rb
+      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/w/with-languages.rb
       ==> Name
       None
       ==> Description
@@ -107,7 +107,7 @@ describe Cask::Info, :cask do
       ==> without-languages: 1.2.3
       https://brew.sh/
       Not installed
-      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/without-languages.rb
+      From: https://github.com/Homebrew/homebrew-cask/blob/HEAD/Casks/w/without-languages.rb
       ==> Name
       None
       ==> Description
diff --git a/Library/Homebrew/test/cask/upgrade_spec.rb b/Library/Homebrew/test/cask/upgrade_spec.rb
index d29482eb73..9ae9811a33 100644
--- a/Library/Homebrew/test/cask/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/upgrade_spec.rb
@@ -34,6 +34,7 @@ describe Cask::Upgrade, :cask do
 
     before do
       installed.each { |cask| Cask::Installer.new(Cask::CaskLoader.load(cask_path(cask))).install }
+      FileUtils.rm_rf CoreCaskTap.instance.cask_dir/"outdated"
 
       allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
     end
@@ -227,6 +228,7 @@ describe Cask::Upgrade, :cask do
 
     before do
       installed.each { |cask| Cask::Installer.new(Cask::CaskLoader.load(cask_path(cask))).install }
+      FileUtils.rm_rf CoreCaskTap.instance.cask_dir/"outdated"
 
       allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
     end
@@ -412,6 +414,7 @@ describe Cask::Upgrade, :cask do
 
     before do
       installed.each { |cask| Cask::Installer.new(Cask::CaskLoader.load(cask_path(cask))).install }
+      FileUtils.rm_rf CoreCaskTap.instance.cask_dir/"outdated"
 
       allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
     end
@@ -468,6 +471,7 @@ describe Cask::Upgrade, :cask do
 
     before do
       installed.each { |cask| Cask::Installer.new(Cask::CaskLoader.load(cask_path(cask))).install }
+      FileUtils.rm_rf CoreCaskTap.instance.cask_dir/"outdated"
 
       allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
     end
diff --git a/Library/Homebrew/test/livecheck/strategy/extract_plist_spec.rb b/Library/Homebrew/test/livecheck/strategy/extract_plist_spec.rb
index 3cf72bd072..1543498b84 100644
--- a/Library/Homebrew/test/livecheck/strategy/extract_plist_spec.rb
+++ b/Library/Homebrew/test/livecheck/strategy/extract_plist_spec.rb
@@ -108,7 +108,7 @@ describe Homebrew::Livecheck::Strategy::ExtractPlist do
 
   describe "::find_versions" do
     it "returns a for an installer artifact" do
-      cask = Cask::CaskLoader.load(cask_path("livecheck/installer-manual-livecheck"))
+      cask = Cask::CaskLoader.load(cask_path("livecheck/livecheck-installer-manual"))
       installer_artifact = cask.artifacts.first
 
       expect(installer_artifact).to be_a(Cask::Artifact::Installer)
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/discontinued-reference.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-discontinued-reference.rb
similarity index 87%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/discontinued-reference.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-discontinued-reference.rb
index ff6fb834f2..ce833b560c 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/discontinued-reference.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-discontinued-reference.rb
@@ -1,4 +1,4 @@
-cask "discontinued-reference" do
+cask "livecheck-discontinued-reference" do
   version "1.2.3"
   sha256 "8c62a2b791cf5f0da6066a0a4b6e85f62949cd60975da062df44adf887f4370b"
 
@@ -11,7 +11,7 @@ cask "discontinued-reference" do
   homepage "http://localhost/homebrew/test/cask/audit/livecheck/discontinued"
 
   livecheck do
-    cask "livecheck/discontinued"
+    cask "livecheck/livecheck-discontinued"
   end
 
   app "TestCask.app"
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/discontinued.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-discontinued.rb
similarity index 94%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/discontinued.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-discontinued.rb
index eb9a50c816..9ecf72b7a5 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/discontinued.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-discontinued.rb
@@ -1,4 +1,4 @@
-cask "discontinued" do
+cask "livecheck-discontinued" do
   version "1.2.3"
   sha256 "8c62a2b791cf5f0da6066a0a4b6e85f62949cd60975da062df44adf887f4370b"
 
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/installer-manual-livecheck.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-installer-manual.rb
similarity index 90%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/installer-manual-livecheck.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-installer-manual.rb
index 98f1b06901..fe38c3ce09 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/installer-manual-livecheck.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-installer-manual.rb
@@ -1,4 +1,4 @@
-cask "installer-manual-livecheck" do
+cask "livecheck-installer-manual" do
   version "1.2.3"
   sha256 "78c670559a609f5d89a5d75eee49e2a2dab48aa3ea36906d14d5f7104e483bb9"
 
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/url-unversioned-reference.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-url-unversioned-reference.rb
similarity index 87%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/url-unversioned-reference.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-url-unversioned-reference.rb
index 078caa0bde..1fe96752be 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/url-unversioned-reference.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-url-unversioned-reference.rb
@@ -1,4 +1,4 @@
-cask "url-unversioned-reference" do
+cask "livecheck-url-unversioned-reference" do
   version "1.2.3"
   sha256 "8c62a2b791cf5f0da6066a0a4b6e85f62949cd60975da062df44adf887f4370b"
 
@@ -11,7 +11,7 @@ cask "url-unversioned-reference" do
   homepage "http://localhost/homebrew/test/cask/audit/livecheck/url-unversioned"
 
   livecheck do
-    cask "livecheck/url-unversioned"
+    cask "livecheck/livecheck-url-unversioned"
   end
 
   app "TestCask.app"
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/url-unversioned.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-url-unversioned.rb
similarity index 94%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/url-unversioned.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-url-unversioned.rb
index c696ae0696..8208a26590 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/url-unversioned.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-url-unversioned.rb
@@ -1,4 +1,4 @@
-cask "url-unversioned" do
+cask "livecheck-url-unversioned" do
   version "1.2.3"
   sha256 "8c62a2b791cf5f0da6066a0a4b6e85f62949cd60975da062df44adf887f4370b"
 
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/version-latest-reference.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-version-latest-reference.rb
similarity index 86%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/version-latest-reference.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-version-latest-reference.rb
index 11f057e3e1..ba3626a52b 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/version-latest-reference.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-version-latest-reference.rb
@@ -1,4 +1,4 @@
-cask "version-latest-reference" do
+cask "livecheck-version-latest-reference" do
   version :latest
   sha256 :no_check
 
@@ -11,7 +11,7 @@ cask "version-latest-reference" do
   homepage "http://localhost/homebrew/test/cask/audit/livecheck/version-latest"
 
   livecheck do
-    cask "livecheck/version-latest"
+    cask "livecheck/livecheck-version-latest"
   end
 
   app "TestCask.app"
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/version-latest.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-version-latest.rb
similarity index 93%
rename from Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/version-latest.rb
rename to Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-version-latest.rb
index 37286c09c2..3e892077e1 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/version-latest.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/livecheck/livecheck-version-latest.rb
@@ -1,4 +1,4 @@
-cask "version-latest" do
+cask "livecheck-version-latest" do
   version :latest
   sha256 :no_check
 
diff --git a/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb b/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
index 003705110a..67f9078c95 100644
--- a/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
+++ b/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
@@ -39,21 +39,23 @@ RSpec.shared_context "Homebrew Cask", :needs_macos do # rubocop:disable RSpec/Co
       Cask::Config::DEFAULT_DIRS_PATHNAMES.each_value(&:mkpath)
 
       CoreCaskTap.instance.tap do |tap|
-        FileUtils.mkdir_p tap.path.dirname
-        FileUtils.ln_sf TEST_FIXTURE_DIR.join("cask"), tap.path
+        tap.cask_dir.mkpath
+        (TEST_FIXTURE_DIR/"cask/Casks").children.each do |casks_path|
+          FileUtils.ln_sf casks_path, tap.cask_dir
+        end
       end
 
       third_party_tap.tap do |tap|
-        FileUtils.mkdir_p tap.path.dirname
-        FileUtils.ln_sf TEST_FIXTURE_DIR.join("third-party"), tap.path
+        tap.path.parent.mkpath
+        FileUtils.ln_sf TEST_FIXTURE_DIR/"third-party", tap.path
       end
 
       example.run
     ensure
       FileUtils.rm_rf Cask::Config::DEFAULT_DIRS_PATHNAMES.values
       FileUtils.rm_rf [Cask::Config.new.binarydir, Cask::Caskroom.path, Cask::Cache.path]
-      CoreCaskTap.instance.path.unlink
-      third_party_tap.path.unlink
+      FileUtils.rm_rf CoreCaskTap.instance.path
+      FileUtils.rm_rf third_party_tap.path
       FileUtils.rm_rf third_party_tap.path.parent
     end
   end