diff --git a/modules/lang/org/autoload/org.el b/modules/lang/org/autoload/org.el
index 390756ab5..6ca0017b3 100644
--- a/modules/lang/org/autoload/org.el
+++ b/modules/lang/org/autoload/org.el
@@ -142,7 +142,7 @@ wrong places)."
                         (- (point) (line-beginning-position)))))
              (save-match-data
                (pcase direction
-                 ('below
+                 (`below
                   (org-end-of-item)
                   (backward-char)
                   (end-of-line)
@@ -153,7 +153,7 @@ wrong places)."
                           (org-next-item)
                           (org-end-of-line)))
                     (insert "\n" (make-string pad 32) (or marker ""))))
-                 ('above
+                 (`above
                   (goto-char (line-beginning-position))
                   (if (and marker (string-match-p "[0-9]+[).]" marker))
                       (org-insert-item)
@@ -174,8 +174,9 @@ wrong places)."
                             (org-element-property :level context)
                           1)))
              (pcase direction
-               ('below
-                (let ((at-eol (= (point) (1- (line-end-position)))))
+               (`below
+                (let ((at-eol (>= (point) (1- (line-end-position))))
+                      org-insert-heading-respect-content)
                   (goto-char (line-end-position))
                   (org-end-of-subtree)
                   (insert (concat "\n"
@@ -185,11 +186,12 @@ wrong places)."
                                       "\n"))
                                   (make-string level ?*)
                                   " "))))
-               ('above
+               (`above
                 (org-back-to-heading)
-                (org-insert-heading)
-                (when (= level 1)
-                  (save-excursion (insert "\n")))))
+                (insert (make-string level ?*) " ")
+                (save-excursion
+                  (insert "\n")
+                  (if (= level 1) (insert "\n")))))
              (when (org-element-property :todo-type context)
                (org-todo 'todo))))
 
diff --git a/modules/lang/org/test/autoload-org.el b/modules/lang/org/test/autoload-org.el
index 567f1abcf..dad80d52a 100644
--- a/modules/lang/org/test/autoload-org.el
+++ b/modules/lang/org/test/autoload-org.el
@@ -1,6 +1,8 @@
 ;; -*- no-byte-compile: t; -*-
 ;;; lang/org/test/autoload-org.el
 
+(require! :lang org)
+
 (defmacro should-org-buffer!! (source expected &rest body)
   `(should-buffer!! ,source ,expected
      (org-mode)
@@ -40,3 +42,21 @@ newline."
                        "+ {|}"
                        "+ Next item")
     (+org/insert-item 'below)))
+
+(def-test! insert-item-numbered-list
+  "Should append/prepend new second-level (and higher) headers without an extra
+newline."
+  (should-org-buffer!! ("1. {0}List item") ("1. List item\n2. {|}")
+    (+org/insert-item 'below))
+  (should-org-buffer!! ("1. {0}List item"
+                       "2. Sub item")
+                      ("1. List item"
+                       "2. {|}"
+                       "3. Sub item")
+    (+org/insert-item 'below))
+  (should-org-buffer!! ("1. {0}List item"
+                       "2. Next item")
+                      ("1. {|}"
+                       "2. List item"
+                       "3. Next item")
+    (+org/insert-item 'above)))
diff --git a/modules/lang/org/test/org.el b/modules/lang/org/test/org.el
deleted file mode 100644
index b74e7f16e..000000000
--- a/modules/lang/org/test/org.el
+++ /dev/null
@@ -1,5 +0,0 @@
-;;; lang/org/test/org.el -*- lexical-binding: t; -*-
-
-(require! :lang org)
-
-;;