diff --git a/lib/rdoc/generator/template/rails/_context.rhtml b/lib/rdoc/generator/template/rails/_context.rhtml
index 13f868ec..a3883bf4 100644
--- a/lib/rdoc/generator/template/rails/_context.rhtml
+++ b/lib/rdoc/generator/template/rails/_context.rhtml
@@ -14,7 +14,7 @@
     <div class="sectiontitle">Required Files</div>
     <ul>
       <% context.requires.each do |req| %>
-        <li><%= h req.name %></li>
+        <li><%= full_name req.name %></li>
       <% end %>
     </ul>
   <% end %>
@@ -58,9 +58,9 @@
       <% context.includes.each do |inc| %>
         <li>
           <% if inc.module.is_a?(String) %>
-            <%= h inc.name %>
+            <%= full_name inc.name %>
           <% else %>
-            <%= link_to inc.module.full_name, inc.module %>
+            <%= link_to inc.module %>
           <% end %>
         </li>
       <% end %>
@@ -144,7 +144,7 @@
             <p class="aka">
               Also aliased as:
               <%# Sometimes a parent cannot be determined. See ruby/rdoc@85ebfe13dc. %>
-              <%= method.aliases.map { |aka| link_to aka.name, (aka if aka.parent) }.join(", ") %>.
+              <%= method.aliases.map { |aka| link_to_if aka.parent, aka.name, aka }.join(", ") %>.
             </p>
           <% end %>
 
@@ -191,7 +191,7 @@
       <% (context.modules.sort + context.classes.sort).each do |mod| %>
         <li>
           <span class="type"><%= mod.type.upcase %></span>
-          <%= link_to mod.full_name, mod %>
+          <%= link_to mod %>
         </li>
       <% end %>
     </ul>
diff --git a/lib/rdoc/generator/template/rails/class.rhtml b/lib/rdoc/generator/template/rails/class.rhtml
index ac2fa21d..55c1bcbc 100644
--- a/lib/rdoc/generator/template/rails/class.rhtml
+++ b/lib/rdoc/generator/template/rails/class.rhtml
@@ -28,14 +28,10 @@
 
         <h2>
             <span class="type"><%= klass.module? ? 'Module' : 'Class' %></span>
-            <%= h klass.full_name %>
-            <% if klass.type == "class" && klass.superclass %>
-                <span class="parent">&lt;
-                    <% if klass.superclass.is_a?(String) %>
-                    <%= klass.superclass %>
-                    <% else %>
-                    <%= link_to klass.superclass.full_name, klass.superclass %>
-                    <% end %>
+            <%= full_name klass %>
+            <% if klass.type == "class" && superclass = klass.superclass %>
+                <span class="parent">
+                    &lt; <%= superclass.is_a?(String) ? full_name(superclass) : link_to(superclass) %>
                 </span>
             <% end %>
         </h2>
@@ -51,7 +47,7 @@
                 <summary class="sectiontitle">Appears in</summary>
                 <ul class="files">
                     <% klass.in_files.each do |file| %>
-                    <li><%= link_to file.absolute_name, file %></li>
+                    <li><%= link_to file %></li>
                     <% end %>
                 </ul>
             </details>
diff --git a/lib/rdoc/generator/template/rails/file.rhtml b/lib/rdoc/generator/template/rails/file.rhtml
index a681c0c2..cac4f0ca 100644
--- a/lib/rdoc/generator/template/rails/file.rhtml
+++ b/lib/rdoc/generator/template/rails/file.rhtml
@@ -28,7 +28,7 @@
         </h2>
         <ul class="files">
             <li>
-                <%= h file.relative_name %>
+                <%= full_name file %>
                 <% if github = github_url(file.relative_name) %>
                     <a href="<%= github %>" target="_blank" class="github_url">on GitHub</a>
                 <% end %>
diff --git a/lib/sdoc/helpers.rb b/lib/sdoc/helpers.rb
index 84069f93..72603210 100644
--- a/lib/sdoc/helpers.rb
+++ b/lib/sdoc/helpers.rb
@@ -2,13 +2,24 @@ module SDoc::Helpers
   require_relative "helpers/git"
   include SDoc::Helpers::Git
 
-  def link_to(text, url, html_attributes = {})
-    return h(text) if url.nil?
-
-    url = "/#{url.path}" if url.is_a?(RDoc::CodeObject)
+  def link_to(text, url = nil, html_attributes = {})
+    url, html_attributes = nil, url if url.is_a?(Hash)
+    url ||= text
     attribute_string = html_attributes.map { |name, value| %( #{name}="#{h value}") }.join
 
-    %(<a href="#{h url}"#{attribute_string}>#{h text}</a>)
+    %(<a href="#{_link_url url}"#{attribute_string}>#{_link_body text}</a>)
+  end
+
+  def _link_url(url)
+    h(url.is_a?(RDoc::CodeObject) ? "/#{url.path}" : url)
+  end
+
+  def _link_body(text)
+    text.is_a?(RDoc::CodeObject) ? full_name(text) : h(text)
+  end
+
+  def link_to_if(condition, text, *args)
+    condition ? link_to(text, *args) : _link_body(text)
   end
 
   def link_to_external(text, url, html_attributes = {})
@@ -19,6 +30,11 @@ def link_to_external(text, url, html_attributes = {})
     link_to(text, url, html_attributes)
   end
 
+  def full_name(named)
+    named = named.full_name if named.is_a?(RDoc::CodeObject)
+    named.split(%r"(?<=./|.::)").map { |part| h part }.join("<wbr>")
+  end
+
   def base_tag_for_context(context)
     relative_root = "../" * context.path.count("/") if context
     %(<base href="./#{relative_root}" data-current-path="#{context&.path}">)
diff --git a/spec/helpers_spec.rb b/spec/helpers_spec.rb
index 89cc1aa3..c39bf7d9 100644
--- a/spec/helpers_spec.rb
+++ b/spec/helpers_spec.rb
@@ -91,24 +91,61 @@
         must_equal %(<a href="qux" title="Foo &gt; Bar">Bar &lt; Foo</a>)
     end
 
-    it "returns the escaped text when URL argument is nil" do
-      _(@helpers.link_to("Bar < Foo", nil, title: "Foo > Bar")).
-        must_equal %(Bar &lt; Foo)
+    it "uses the first argument as the URL when no URL is specified" do
+      _(@helpers.link_to("foo/bar/qux.html")).
+        must_equal %(<a href="foo/bar/qux.html">foo/bar/qux.html</a>)
+
+      _(@helpers.link_to("foo/bar/qux.html", "data-hoge": "fuga")).
+        must_equal %(<a href="foo/bar/qux.html" data-hoge="fuga">foo/bar/qux.html</a>)
     end
 
-    it "returns an appropriate link when URL argument is an RDoc::CodeObject that responds to #path" do
+    it "uses #full_name when the text argument is an RDoc::CodeObject" do
       top_level = rdoc_top_level_for <<~RUBY
         module Foo; class Bar; def qux; end; end; end
       RUBY
 
-      _(@helpers.link_to("perma", top_level.find_module_named("Foo"))).
-        must_equal %(<a href="/classes/Foo.html">perma</a>)
+      [
+        top_level,
+        top_level.find_module_named("Foo"),
+        top_level.find_module_named("Foo::Bar"),
+        top_level.find_module_named("Foo::Bar").find_method("qux", false),
+      ].each do |code_object|
+        _(@helpers.link_to(code_object, "url")).
+          must_equal %(<a href="url">#{@helpers.full_name(code_object)}</a>)
+      end
+    end
+
+    it "uses RDoc::CodeObject#path as the URL when URL argument is an RDoc::CodeObject" do
+      top_level = rdoc_top_level_for <<~RUBY
+        module Foo; class Bar; def qux; end; end; end
+      RUBY
+
+      [
+        top_level,
+        top_level.find_module_named("Foo"),
+        top_level.find_module_named("Foo::Bar"),
+        top_level.find_module_named("Foo::Bar").find_method("qux", false),
+      ].each do |code_object|
+        _(@helpers.link_to("text", code_object)).
+          must_equal %(<a href="/#{code_object.path}">text</a>)
+      end
+    end
+  end
+
+  describe "#link_to_if" do
+    it "returns the link's HTML when the condition is true" do
+      args = ["Bar < Foo", "qux", title: "Foo > Bar"]
+      _(@helpers.link_to_if(true, *args)).must_equal @helpers.link_to(*args)
+    end
+
+    it "returns the link's inner HTML when the condition is false" do
+      _(@helpers.link_to_if(false, "Bar < Foo", "url")).must_equal ERB::Util.h("Bar < Foo")
 
-      _(@helpers.link_to("perma", top_level.find_module_named("Foo::Bar"))).
-        must_equal %(<a href="/classes/Foo/Bar.html">perma</a>)
+      rdoc_module = rdoc_top_level_for(<<~RUBY).find_module_named("Foo::Bar")
+        module Foo; class Bar; end; end
+      RUBY
 
-      _(@helpers.link_to("perma", top_level.find_module_named("Foo::Bar").find_method("qux", false))).
-        must_equal %(<a href="/classes/Foo/Bar.html#method-i-qux">perma</a>)
+      _(@helpers.link_to_if(false, rdoc_module, "url")).must_equal @helpers.full_name(rdoc_module)
     end
   end
 
@@ -134,6 +171,30 @@ module Foo; class Bar; def qux; end; end; end
     end
   end
 
+  describe "#full_name" do
+    it "inserts word-break opportunities into module names" do
+      _(@helpers.full_name("Foo::Bar::Qux")).must_equal "Foo::<wbr>Bar::<wbr>Qux"
+      _(@helpers.full_name("::Foo::Bar::Qux")).must_equal "::Foo::<wbr>Bar::<wbr>Qux"
+    end
+
+    it "inserts word-break opportunities into file paths" do
+      _(@helpers.full_name("path/to/file.rb")).must_equal "path/<wbr>to/<wbr>file.rb"
+      _(@helpers.full_name("/path/to/file.rb")).must_equal "/path/<wbr>to/<wbr>file.rb"
+    end
+
+    it "escapes name parts" do
+      _(@helpers.full_name("ruby & rails/file.rb")).must_equal "ruby &amp; rails/<wbr>file.rb"
+    end
+
+    it "uses RDoc::CodeObject#full_name when argument is an RDoc::CodeObject" do
+      rdoc_module = rdoc_top_level_for(<<~RUBY).find_module_named("Foo::Bar::Qux")
+        module Foo; module Bar; class Qux; end; end; end
+      RUBY
+
+      _(@helpers.full_name(rdoc_module)).must_equal "Foo::<wbr>Bar::<wbr>Qux"
+    end
+  end
+
   describe "#base_tag_for_context" do
     it "returns an idempotent <base> tag for nil context" do
       _(@helpers.base_tag_for_context(nil)).