diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3e53685..6b4a860 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,7 @@
 # Changes
 
 * 2.3.next in progress
+  * Address [#414](https://github.com/seancorfield/honeysql/issues/414) by providing an example of `ORDER BY` with a `CASE` expression.
   * Address [#412](https://github.com/seancorfield/honeysql/issues/412) by documenting options in a separate page and reorganizing the ToC structure.
   * Address [#409](https://github.com/seancorfield/honeysql/issues/409) by making docstring check for public helpers conditional.
   * Address [#401](https://github.com/seancorfield/honeysql/issues/401) by adding `register-dialect!` and `get-dialect`, and also making `add-clause-before`, `strop`, and `upper-case` public so that new dialects are easier to construct.
diff --git a/doc/clause-reference.md b/doc/clause-reference.md
index bee45b9..ab1d816 100644
--- a/doc/clause-reference.md
+++ b/doc/clause-reference.md
@@ -815,6 +815,12 @@ user=> (sql/format {:select [:*] :from :table
                     ;; expression without direction is still wrapped:
                     :order-by [:status, [[:year :created-date]]]})
 ["SELECT * FROM table ORDER BY status ASC, YEAR(created_date) ASC"]
+;; a more complex order by with case (and direction):
+user=> (sql/format {:select [:*] :from :table
+                    :order-by [[[:case [:< [:now] :expiry-date]
+                                 :created-date :else :expiry-date]
+                                :desc]]})
+["SELECT * FROM table ORDER BY CASE WHEN NOW() < expiry_date THEN created_date ELSE expiry_date END DESC"]
 ```
 
 ## limit, offset, fetch