diff --git a/Library/Homebrew/cleanup.rb b/Library/Homebrew/cleanup.rb
index 16201b3cb0..39b1484f38 100644
--- a/Library/Homebrew/cleanup.rb
+++ b/Library/Homebrew/cleanup.rb
@@ -46,7 +46,8 @@ module Homebrew
 
           return true if symlink? && !exist?
 
-          mtime < days.days.ago && ctime < days.days.ago
+          days_ago = (DateTime.now - days).to_time
+          mtime < days_ago && ctime < days_ago
         end
 
         def stale?(scrub: false)
@@ -125,8 +126,8 @@ module Homebrew
           return true if scrub && cask.versions.exclude?(cask.version)
 
           if cask.version.latest?
-            return mtime < CLEANUP_DEFAULT_DAYS.days.ago &&
-                   ctime < CLEANUP_DEFAULT_DAYS.days.ago
+            cleanup_threshold = (DateTime.now - CLEANUP_DEFAULT_DAYS).to_time
+            return mtime < cleanup_threshold && ctime < cleanup_threshold
           end
 
           false
@@ -202,7 +203,7 @@ module Homebrew
         return false
       end
 
-      PERIODIC_CLEAN_FILE.mtime < CLEANUP_DEFAULT_DAYS.days.ago
+      PERIODIC_CLEAN_FILE.mtime < (DateTime.now - CLEANUP_DEFAULT_DAYS).to_time
     end
 
     def self.periodic_clean!(dry_run: false)
diff --git a/Library/Homebrew/dev-cmd/bump-unversioned-casks.rb b/Library/Homebrew/dev-cmd/bump-unversioned-casks.rb
index fad44a815f..c2aeaf2a49 100644
--- a/Library/Homebrew/dev-cmd/bump-unversioned-casks.rb
+++ b/Library/Homebrew/dev-cmd/bump-unversioned-casks.rb
@@ -65,7 +65,7 @@ module Homebrew
     end
 
     limit = args.limit.presence&.to_i
-    end_time = Time.now + limit.minutes if limit
+    end_time = Time.now + (limit * 60) if limit
 
     until queue.empty? || (end_time && end_time < Time.now)
       cask = queue.deq
@@ -101,7 +101,7 @@ module Homebrew
     last_check_time = state["check_time"]&.then { |t| Time.parse(t) }
 
     check_time = Time.now
-    if last_check_time && check_time < (last_check_time + 1.day)
+    if last_check_time && check_time < (last_check_time + (DateTime.now + 1).to_time)
       opoo "Skipping, already checked within the last 24 hours."
       return
     end
@@ -119,7 +119,7 @@ module Homebrew
 
     if last_time != time || last_file_size != file_size
       sha256 = begin
-        Timeout.timeout(5.minutes) do
+        Timeout.timeout(5 * 60) do
           unversioned_cask_checker.installer.download.sha256
         end
       rescue => e
@@ -128,7 +128,7 @@ module Homebrew
 
       if sha256.present? && last_sha256 != sha256
         version = begin
-          Timeout.timeout(1.minute) do
+          Timeout.timeout(60) do
             unversioned_cask_checker.guess_cask_version
           end
         rescue Timeout::Error
diff --git a/Library/Homebrew/global.rb b/Library/Homebrew/global.rb
index 6291f4b17b..9fddb5fb89 100644
--- a/Library/Homebrew/global.rb
+++ b/Library/Homebrew/global.rb
@@ -13,7 +13,7 @@ require "forwardable"
 # Only require "core_ext" here to ensure we're only requiring the minimum of
 # what we need.
 require "active_support/core_ext/object/blank"
-require "active_support/core_ext/numeric/time"
+require "active_support/core_ext/string/filters"
 require "active_support/core_ext/object/try"
 require "active_support/core_ext/array/access"
 require "active_support/core_ext/string/inflections"
diff --git a/Library/Homebrew/test/cleanup_spec.rb b/Library/Homebrew/test/cleanup_spec.rb
index 007b64753e..13a6bde07c 100644
--- a/Library/Homebrew/test/cleanup_spec.rb
+++ b/Library/Homebrew/test/cleanup_spec.rb
@@ -37,8 +37,8 @@ describe Homebrew::Cleanup do
     end
 
     it "returns true when ctime and mtime < days_default" do
-      allow_any_instance_of(Pathname).to receive(:ctime).and_return(2.days.ago)
-      allow_any_instance_of(Pathname).to receive(:mtime).and_return(2.days.ago)
+      allow_any_instance_of(Pathname).to receive(:ctime).and_return((DateTime.now - 2).to_time)
+      allow_any_instance_of(Pathname).to receive(:mtime).and_return((DateTime.now - 2).to_time)
       expect(path.prune?(1)).to be true
     end
 
@@ -186,8 +186,8 @@ describe Homebrew::Cleanup do
       it "removes the download for the latest version after 30 days" do
         download = Cask::Cache.path/"#{cask.token}--#{cask.version}"
 
-        allow(download).to receive(:ctime).and_return(30.days.ago - 1.hour)
-        allow(download).to receive(:mtime).and_return(30.days.ago - 1.hour)
+        allow(download).to receive(:ctime).and_return((DateTime.now - 30).to_time - (60 * 60))
+        allow(download).to receive(:mtime).and_return((DateTime.now - 30).to_time - (60 * 60))
 
         cleanup.cleanup_cask(cask)
 
@@ -209,15 +209,15 @@ describe Homebrew::Cleanup do
     end
 
     it "cleans up logs if older than 30 days" do
-      allow_any_instance_of(Pathname).to receive(:ctime).and_return(31.days.ago)
-      allow_any_instance_of(Pathname).to receive(:mtime).and_return(31.days.ago)
+      allow_any_instance_of(Pathname).to receive(:ctime).and_return((DateTime.now - 31).to_time)
+      allow_any_instance_of(Pathname).to receive(:mtime).and_return((DateTime.now - 31).to_time)
       cleanup.cleanup_logs
       expect(path).not_to exist
     end
 
     it "does not clean up logs less than 30 days old" do
-      allow_any_instance_of(Pathname).to receive(:ctime).and_return(15.days.ago)
-      allow_any_instance_of(Pathname).to receive(:mtime).and_return(15.days.ago)
+      allow_any_instance_of(Pathname).to receive(:ctime).and_return((DateTime.now - 15).to_time)
+      allow_any_instance_of(Pathname).to receive(:mtime).and_return((DateTime.now - 15).to_time)
       cleanup.cleanup_logs
       expect(path).to exist
     end