diff --git a/config/routes.rb b/config/routes.rb
index af58e095d9a..8dbe6d80ab7 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -39,7 +39,7 @@ Gitlab::Application.routes.draw do
 
   # Help
   get 'help'                  => 'help#index'
-  get 'help/:category/:file'  => 'help#show', as: :help_page
+  get 'help/:category/:file'  => 'help#show', as: :help_page, constraints: { category: /[^\.]+/, file: /[^\.]+/ }
   get 'help/shortcuts'
   get 'help/ui'               => 'help#ui'
 
diff --git a/spec/routing/routing_spec.rb b/spec/routing/routing_spec.rb
index d4915b51952..b1225f101b7 100644
--- a/spec/routing/routing_spec.rb
+++ b/spec/routing/routing_spec.rb
@@ -64,50 +64,35 @@ describe SnippetsController, "routing" do
   end
 end
 
-#              help GET    /help(.:format)              help#index
-#  help_permissions GET    /help/permissions(.:format)  help#permissions
-#     help_workflow GET    /help/workflow(.:format)     help#workflow
-#          help_api GET    /help/api(.:format)          help#api
-#    help_web_hooks GET    /help/web_hooks(.:format)    help#web_hooks
-# help_system_hooks GET    /help/system_hooks(.:format) help#system_hooks
-#     help_markdown GET    /help/markdown(.:format)     help#markdown
-#          help_ssh GET    /help/ssh(.:format)          help#ssh
-#    help_raketasks GET    /help/raketasks(.:format)    help#raketasks
+#            help GET /help(.:format)                 help#index
+#       help_page GET /help/:category/:file(.:format) help#show {:category=>/[^\.]+/, :file=>/[^\.]+/}
+#  help_shortcuts GET /help/shortcuts(.:format)       help#shortcuts
+#         help_ui GET /help/ui(.:format)              help#ui
 describe HelpController, "routing" do
   it "to #index" do
     expect(get("/help")).to route_to('help#index')
   end
 
-  it "to #permissions" do
-    expect(get("/help/permissions/permissions")).to route_to('help#show', category: "permissions", file: "permissions")
+  it 'to #show' do
+    path = '/help/markdown/markdown.md'
+    expect(get(path)).to route_to('help#show',
+                                  category: 'markdown',
+                                  file: 'markdown',
+                                  format: 'md')
+
+    path = '/help/workflow/protected_branches/protected_branches1.png'
+    expect(get(path)).to route_to('help#show',
+                                  category: 'workflow/protected_branches',
+                                  file: 'protected_branches1',
+                                  format: 'png')
   end
 
-  it "to #workflow" do
-    expect(get("/help/workflow/README")).to route_to('help#show', category: "workflow", file: "README")
+  it 'to #shortcuts' do
+    expect(get('/help/shortcuts')).to route_to('help#shortcuts')
   end
 
-  it "to #api" do
-    expect(get("/help/api/README")).to route_to('help#show', category: "api", file: "README")
-  end
-
-  it "to #web_hooks" do
-    expect(get("/help/web_hooks/web_hooks")).to route_to('help#show', category: "web_hooks", file: "web_hooks")
-  end
-
-  it "to #system_hooks" do
-    expect(get("/help/system_hooks/system_hooks")).to route_to('help#show', category: "system_hooks", file: "system_hooks")
-  end
-
-  it "to #markdown" do
-    expect(get("/help/markdown/markdown")).to route_to('help#show',category: "markdown", file: "markdown")
-  end
-
-  it "to #ssh" do
-    expect(get("/help/ssh/README")).to route_to('help#show', category: "ssh", file: "README")
-  end
-
-  it "to #raketasks" do
-    expect(get("/help/raketasks/README")).to route_to('help#show', category: "raketasks", file: "README")
+  it 'to #ui' do
+    expect(get('/help/ui')).to route_to('help#ui')
   end
 end