diff --git a/lib/rake/file_task.rb b/lib/rake/file_task.rb
index 6656e7095..cbb978e7f 100644
--- a/lib/rake/file_task.rb
+++ b/lib/rake/file_task.rb
@@ -29,7 +29,14 @@ def timestamp
 
     # Are there any prerequisites with a later time than the given time stamp?
     def out_of_date?(stamp)
-      @prerequisites.any? { |n| application[n, @scope].timestamp > stamp }
+      @prerequisites.any? { |prereq|
+        prereq_task = application[prereq, @scope]
+        if prereq_task.instance_of?(Rake::FileTask)
+          prereq_task.timestamp > stamp || prereq_task.needed?
+        else
+          prereq_task.timestamp > stamp
+        end
+      }
     end
 
     # ----------------------------------------------------------------
diff --git a/test/support/rakefile_definitions.rb b/test/support/rakefile_definitions.rb
index e0af05a67..9a19d43fc 100644
--- a/test/support/rakefile_definitions.rb
+++ b/test/support/rakefile_definitions.rb
@@ -77,6 +77,24 @@ def rakefile_chains
     DEFAULT
   end
 
+  def rakefile_file_chains
+    rakefile <<-RAKEFILE
+file "fileA" do |t|
+  sh "echo contentA >\#{t.name}"
+end
+
+file "fileB" => "fileA" do |t|
+  sh "(cat fileA; echo transformationB) >\#{t.name}"
+end
+
+file "fileC" => "fileB" do |t|
+  sh "(cat fileB; echo transformationC) >\#{t.name}"
+end
+
+task default: "fileC"
+    RAKEFILE
+  end
+
   def rakefile_comments
     rakefile <<-COMMENTS
 # comment for t1
diff --git a/test/test_rake_functional.rb b/test/test_rake_functional.rb
index 7c2bd3266..3496bc12d 100644
--- a/test/test_rake_functional.rb
+++ b/test/test_rake_functional.rb
@@ -295,6 +295,26 @@ def test_rules_chaining_to_file_task
            "'play.app' file should exist"
   end
 
+  def dryrun_tasks
+    @err.split("\n").select { |line|
+      line.match(/^\*\* Execute/)
+    }.map { |line|
+      line.gsub(/^\*\* Execute \(dry run\) /, "")
+    }
+  end
+
+  def test_update_midway_through_chaining_to_file_task
+    rakefile_file_chains
+
+    rake "-n"
+    assert_equal(%w{fileA fileB fileC default}, dryrun_tasks)
+    rake
+    sleep 1 # Ensure the timestamp is on a new second
+    FileUtils.touch("fileA")
+    rake "-n"
+    assert_equal(%w{fileB fileC default}, dryrun_tasks)
+  end
+
   def test_file_creation_task
     rakefile_file_creation