diff --git a/docs/_docs/index.md b/docs/_docs/index.md
index d71629fe..b3a6c7fd 100644
--- a/docs/_docs/index.md
+++ b/docs/_docs/index.md
@@ -1,7 +1,10 @@
 ---
 title: Quickstart
 permalink: /docs/
-redirect_from: /docs/home/index.html
+redirect_from:
+  - /docs/home/
+  - /docs/quickstart/
+  - /docs/extras/
 ---
 Jekyll is a simple, extendable, static site generator. You give it text written
 in your favorite markup language and it churns through layouts to create a
diff --git a/docs/_docs/installation/windows.md b/docs/_docs/installation/windows.md
index ebb3ae86..d8541088 100644
--- a/docs/_docs/installation/windows.md
+++ b/docs/_docs/installation/windows.md
@@ -1,7 +1,8 @@
 ---
 title: Jekyll on Windows
 permalink: /docs/installation/windows/
-redirect_from: "/docs/windows.html"
+redirect_from:
+  - /docs/windows/
 ---
 
 While Windows is not an officially-supported platform, it can be used to run Jekyll with the proper tweaks. This page aims to collect some of the general knowledge and lessons that have been unearthed by Windows users.
diff --git a/docs/_docs/posts.md b/docs/_docs/posts.md
index d55537a6..7b5c9711 100644
--- a/docs/_docs/posts.md
+++ b/docs/_docs/posts.md
@@ -1,6 +1,8 @@
 ---
 title: Posts
 permalink: /docs/posts/
+redirect_from:
+  - /docs/drafts/
 ---
 
 Blogging is baked into Jekyll. You write blog posts as text files and Jekyll
diff --git a/docs/pages/showcase.html b/docs/pages/showcase.html
index 4c45abf4..2913a25a 100644
--- a/docs/pages/showcase.html
+++ b/docs/pages/showcase.html
@@ -2,6 +2,8 @@
 layout: page
 title: Showcase
 permalink: /showcase/
+redirect_from:
+  - /docs/sites/
 ---
 
 <p>Jekyll is used for all kinds of usecases. Here's some of our favorites:</p>