diff --git a/app/helpers/markdownify_helper.rb b/app/helpers/markdownify_helper.rb
index 3eb8783fa..5d82f33a6 100644
--- a/app/helpers/markdownify_helper.rb
+++ b/app/helpers/markdownify_helper.rb
@@ -118,6 +118,7 @@ module MarkdownifyHelper
       ":-("   => "☹",
       ":)"    => "☺",
       ":-)"   => "☺",
+      "<->" => "↔",
       "->" => "→",
       "<-" => "←",
       "..."   => "…",
diff --git a/spec/helpers/markdownify_helper_spec.rb b/spec/helpers/markdownify_helper_spec.rb
index 7bfb4b3b8..b9feb7fd0 100644
--- a/spec/helpers/markdownify_helper_spec.rb
+++ b/spec/helpers/markdownify_helper_spec.rb
@@ -157,8 +157,8 @@ describe MarkdownifyHelper do
       end
 
       it "replaces various things with (their) HTML entities" do
-        message = ":) :-) :( :-( ... -> <- (tm) (r) (c)"
-        markdownify(message).should == "&#9786; &#9786; &#9785; &#9785; &hellip; &rarr; &larr; &trade; &reg; &copy;"
+        message = ":) :-) :( :-( ... <-> -> <- (tm) (r) (c)"
+        markdownify(message).should == "&#9786; &#9786; &#9785; &#9785; &hellip; &#8596; &rarr; &larr; &trade; &reg; &copy;"
       end
 
       it "skips doing it if you say so" do