diff --git a/app/helpers/messages_helper.rb b/app/helpers/messages_helper.rb
index 687d9a4..6bef743 100644
--- a/app/helpers/messages_helper.rb
+++ b/app/helpers/messages_helper.rb
@@ -118,13 +118,13 @@ module MessagesHelper
 
     # auto_link finds URLs and email addresses with regular expressions, which
     # can't tell an attribute value from text. Hand it one text node at a time,
-    # escaped, so a link can only land between tags.
+    # escaped as the serializer writes text, so a link can only land between tags.
     def auto_link_text(html)
       fragment = Nokogiri::HTML5.fragment(sanitize(html, tags: AUTO_LINK_ALLOWED_TAGS, attributes: AUTO_LINK_ALLOWED_ATTRIBUTES))
 
       fragment.xpath(".//text()[not(ancestor::a)]").each do |node|
         if node.text.match?(LINKABLE_TEXT)
-          text = h(node.text)
+          text = node.to_html
           linked = auto_link(text, html: { target: "_blank" })
           node.replace Nokogiri::HTML5.fragment(linked) unless linked == text
         end
diff --git a/test/helpers/messages_helper_test.rb b/test/helpers/messages_helper_test.rb
index 911317a..83902f5 100644
--- a/test/helpers/messages_helper_test.rb
+++ b/test/helpers/messages_helper_test.rb
@@ -46,6 +46,13 @@ class MessagesHelperTest < ActionView::TestCase
     assert_equal [ "https://example.com/a?b=1&c=2", "me@example.com" ], links.map(&:text)
   end
 
+  test "message_presentation links an email address with an apostrophe whole" do
+    message = Message.create! room: rooms(:pets), body: "<div>Write to o'brien@example.com</div>", client_message_id: "0015", creator: users(:jason)
+
+    links = Nokogiri::HTML5.fragment(view.message_presentation(message)).css("a")
+    assert_equal [ [ "mailto:o%27brien@example.com", "o'brien@example.com" ] ], links.map { [ it["href"], it.text ] }
+  end
+
   test "message_presentation leaves URLs and email addresses in attribute values as they are" do
     [ "class", "title" ].product([ "https://example.com", "www.example.com", "me@example.com" ]).each do |attribute, linkable|
       value = "a> #{linkable} <em>b</em> "