diff --git a/Library/Homebrew/cask/download.rb b/Library/Homebrew/cask/download.rb
index eb3a444bc4..4bd4e4426a 100644
--- a/Library/Homebrew/cask/download.rb
+++ b/Library/Homebrew/cask/download.rb
@@ -35,7 +35,7 @@ module Cask
     attr_accessor :downloaded_path
 
     def clear_cache
-      downloader.clear_cache if force || cask.version.latest?
+      downloader.clear_cache if force
     end
 
     def fetch
diff --git a/Library/Homebrew/download_strategy.rb b/Library/Homebrew/download_strategy.rb
index 5afb8c13ed..924c17f117 100644
--- a/Library/Homebrew/download_strategy.rb
+++ b/Library/Homebrew/download_strategy.rb
@@ -296,6 +296,8 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
 
       fresh = if cached_location.exist? && url_time
         url_time <= cached_location.mtime
+      elsif version.respond_to?(:latest?)
+        !version.latest?
       else
         true
       end