diff --git a/Library/Homebrew/cmd/update.rb b/Library/Homebrew/cmd/update.rb
index 08062e15b5..9e2541434e 100644
--- a/Library/Homebrew/cmd/update.rb
+++ b/Library/Homebrew/cmd/update.rb
@@ -247,7 +247,13 @@ class Updater
     end
 
     if @initial_branch != @upstream_branch && !@initial_branch.empty?
-      safe_system "git", "checkout", "--force", "-B", @upstream_branch, "origin/#{@upstream_branch}", *@quiet_args
+      # Recreate and check out `#{upstream_branch}` if unable to fast-forward
+      # it to `origin/#{@upstream_branch}`. Otherwise, just check it out.
+      if system("git", "merge-base", "--is-ancestor", @upstream_branch, "origin/#{@upstream_branch}")
+        safe_system "git", "checkout", "--force", @upstream_branch, *@quiet_args
+      else
+        safe_system "git", "checkout", "--force", "-B", @upstream_branch, "origin/#{@upstream_branch}", *@quiet_args
+      end
     end
 
     @initial_revision = read_current_revision