diff --git a/modules/org/org/test/autoload-org.el b/modules/org/org/test/autoload-org.el
new file mode 100644
index 000000000..d9ac443d0
--- /dev/null
+++ b/modules/org/org/test/autoload-org.el
@@ -0,0 +1,42 @@
+;; -*- no-byte-compile: t; -*-
+;;; org/org/test/autoload-org.el
+
+(defmacro should-org-buffer! (source expected &rest body)
+  `(should-buffer! ,source ,expected
+     (org-mode)
+     ,@body))
+
+
+;; `+org/insert-item'
+(def-test! insert-item-h1
+  "Should append/prepend new first-level headers with an extra newline."
+  (should-org-buffer! ("* {0}Header") ("* Header\n\n* {|}")
+    (+org/insert-item 'below))
+  (should-org-buffer! ("* {0}Header") ("* {|}\n\n* Header")
+    (+org/insert-item 'above)))
+
+(def-test! insert-item-h2
+  "Should append/prepend new second-level (and higher) headers without an extra
+newline."
+  (should-org-buffer! ("** {0}Header") ("** Header\n** {|}")
+    (+org/insert-item 'below))
+  (should-org-buffer! ("** {0}Header") ("** {|}\n** Header")
+    (+org/insert-item 'above)))
+
+(def-test! insert-item-plain-list
+  "Should append/prepend new second-level (and higher) headers without an extra
+newline."
+  (should-org-buffer! ("+ {0}List item") ("+ List item\n+ {|}")
+    (+org/insert-item 'below))
+  (should-org-buffer! ("+ {0}List item"
+                       "  + Sub item")
+                      ("+ List item"
+                       "  + Sub item"
+                       "+ {|}")
+    (+org/insert-item 'below))
+  (should-org-buffer! ("+ {0}List item"
+                       "+ Next item")
+                      ("+ List item"
+                       "+ {|}"
+                       "+ Next item")
+    (+org/insert-item 'below)))
diff --git a/modules/org/org/test/org.el b/modules/org/org/test/org.el
new file mode 100644
index 000000000..d91044ff9
--- /dev/null
+++ b/modules/org/org/test/org.el
@@ -0,0 +1,5 @@
+;;; org/org/test/org.el -*- lexical-binding: t; -*-
+
+(when (featurep 'org) (unload-feature 'org t))
+(require! :org org)
+(require 'org (locate-library "org" nil doom--package-load-path))