diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index 82aa4fd467866..206f0d380a9db 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -24,6 +24,8 @@ class AbstractUninstall < AbstractArtifact
         :rmdir,
       ].freeze
 
+      TRASH_SCRIPT = (HOMEBREW_LIBRARY_PATH/"cask/utils/trash.swift").freeze
+
       def self.from_args(cask, **directives)
         new(cask, directives)
       end
@@ -318,28 +320,7 @@ def uninstall_trash(*paths, **options)
       end
 
       def trash_paths(*paths, command: nil, **_)
-        result = command.run!("osascript", args: ["-e", <<~APPLESCRIPT, *paths])
-          on run argv
-            repeat with i from 1 to (count argv)
-              set item i of argv to (item i of argv as POSIX file)
-            end repeat
-
-            tell application "Finder"
-              set trashedItems to (move argv to trash)
-              set output to ""
-
-              repeat with i from 1 to (count trashedItems)
-                set trashedItem to POSIX path of (item i of trashedItems as string)
-                set output to output & trashedItem
-                if i < count trashedItems then
-                  set output to output & character id 0
-                end if
-              end repeat
-
-              return output
-            end tell
-          end run
-        APPLESCRIPT
+        result = command.run!("/usr/bin/swift", args: [TRASH_SCRIPT, *paths])
 
         # Remove AppleScript's automatic newline.
         result.tap { |r| r.stdout.sub!(/\n$/, "") }
diff --git a/Library/Homebrew/cask/utils/trash.swift b/Library/Homebrew/cask/utils/trash.swift
new file mode 100644
index 0000000000000..cddbd686ccd4c
--- /dev/null
+++ b/Library/Homebrew/cask/utils/trash.swift
@@ -0,0 +1,22 @@
+#!/usr/bin/swift
+
+import Foundation
+
+if (CommandLine.arguments.count < 2) {
+  exit(2)
+}
+
+let manager: FileManager = FileManager()
+
+for item in CommandLine.arguments[1...] {
+  do {
+    let path: URL = URL(fileURLWithPath: item)
+    try manager.trashItem(at: path, resultingItemURL: nil)
+    print(path)
+  }
+  catch {
+    print("\0")
+  }
+}
+
+exit(0)
diff --git a/Library/Homebrew/dev-cmd/tap-new.rb b/Library/Homebrew/dev-cmd/tap-new.rb
index db5e742c15626..9631a25a1b9df 100644
--- a/Library/Homebrew/dev-cmd/tap-new.rb
+++ b/Library/Homebrew/dev-cmd/tap-new.rb
@@ -54,11 +54,11 @@ def tap_new
       jobs:
       - job: macOS
         pool:
-          vmImage: macOS-10.13
+          vmImage: macOS-10.14
         steps:
           - bash: |
               set -e
-              sudo xcode-select --switch /Applications/Xcode_10.1.app/Contents/Developer
+              sudo xcode-select --switch /Applications/Xcode_10.2.app/Contents/Developer
               brew update
               HOMEBREW_TAP_DIR="/usr/local/Homebrew/Library/Taps/#{tap.full_name}"
               mkdir -p "$HOMEBREW_TAP_DIR"
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index e1dea13014230..30bbdd14f3619 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -1,11 +1,11 @@
 jobs:
 - job: macOS
   pool:
-    vmImage: macOS-10.13
+    vmImage: macOS-10.14
   steps:
     - bash: |
         set -e
-        sudo xcode-select --switch /Applications/Xcode_10.1.app/Contents/Developer
+        sudo xcode-select --switch /Applications/Xcode_10.2.app/Contents/Developer
         HOMEBREW_REPOSITORY="$(brew --repo)"
         mv "$HOMEBREW_REPOSITORY/Library/Taps" "$PWD/Library"
         sudo rm -rf "$HOMEBREW_REPOSITORY"