diff --git a/Library/Homebrew/cmd/update-report.rb b/Library/Homebrew/cmd/update-report.rb
index bb7cbfc23b..4d018290e8 100644
--- a/Library/Homebrew/cmd/update-report.rb
+++ b/Library/Homebrew/cmd/update-report.rb
@@ -257,9 +257,12 @@ class Reporter
       # For formulae migrated to cask: Auto-install cask or provide install instructions.
       if new_tap_name == "caskroom/cask"
         if new_tap.installed? && (HOMEBREW_REPOSITORY/"Caskroom").directory?
-          ohai "#{name} has been moved to Homebrew Cask. Installing #{name}..."
+          ohai "#{name} has been moved to Homebrew Cask."
+          ohai "brew uninstall --force #{name}"
           system HOMEBREW_BREW_FILE, "uninstall", "--force", name
+          ohai "brew prune"
           system HOMEBREW_BREW_FILE, "prune"
+          ohai "brew cask install #{name}"
           system HOMEBREW_BREW_FILE, "cask", "install", name
         else
           ohai "#{name} has been moved to Homebrew Cask.", <<-EOS.undent