diff --git a/lib/handlers/li.js b/lib/handlers/li.js
index 1784ceb..017a34d 100644
--- a/lib/handlers/li.js
+++ b/lib/handlers/li.js
@@ -4,6 +4,8 @@
  * @typedef {import('../state.js').State} State
  */
 
+import {phrasing} from 'hast-util-phrasing'
+
 /**
  * @param {State} state
  *   State.
@@ -42,15 +44,56 @@ export function li(state, node) {
     }
   }
 
-  const children = state.toFlow(state.all(clone || node))
+  if (!clone) clone = node
+
+  const spread = spreadout(clone)
+  const children = state.toFlow(state.all(clone))
 
   /** @type {ListItem} */
-  const result = {
-    type: 'listItem',
-    spread: children.length > 1,
-    checked,
-    children
-  }
-  state.patch(node, result)
+  const result = {type: 'listItem', spread, checked, children}
+  state.patch(clone, result)
   return result
 }
+
+/**
+ * Check if an element should spread out.
+ *
+ * The reason to spread out a markdown list item is primarily whether writing
+ * the equivalent in markdown, would yield a spread out item.
+ *
+ * A spread out item results in `<p>` and `</p>` tags.
+ * Otherwise, the phrasing would be output directly.
+ * We can check for that: if there’s a `<p>` element, spread it out.
+ *
+ * But what if there are no paragraphs?
+ * In that case, we can also assume that if two “block” things were written in
+ * an item, that it is spread out, because blocks are typically joined by blank
+ * lines, which also means a spread item.
+ *
+ * Lastly, because in HTML things can be wrapped in a `<div>` or similar, we
+ * delve into non-phrasing elements here to figure out if they themselves
+ * contain paragraphs or 2 or more flow non-phrasing elements.
+ *
+ * @param {Element} node
+ * @returns {boolean}
+ */
+function spreadout(node) {
+  let index = -1
+  let seenFlow = false
+
+  while (++index < node.children.length) {
+    const child = node.children[index]
+
+    if (child.type === 'element') {
+      if (phrasing(child)) continue
+
+      if (child.tagName === 'p' || seenFlow || spreadout(child)) {
+        return true
+      }
+
+      seenFlow = true
+    }
+  }
+
+  return false
+}
diff --git a/test/fixtures/dl/index.json b/test/fixtures/dl/index.json
index a875830..fe70035 100644
--- a/test/fixtures/dl/index.json
+++ b/test/fixtures/dl/index.json
@@ -1,3 +1,5 @@
 {
+  "": "spread can’t be losslessly translated between HTML <> markdown",
+  "tree": false,
   "fragment": true
 }
diff --git a/test/fixtures/dl/index.md b/test/fixtures/dl/index.md
index 1150ed7..f538704 100644
--- a/test/fixtures/dl/index.md
+++ b/test/fixtures/dl/index.md
@@ -22,7 +22,9 @@ Charlie.
 *   Firefox
 
     *   A web browser.
+
     *   A Red Panda.
+
     *   ```js
         charlie();
         ```
diff --git a/test/fixtures/ol/index.json b/test/fixtures/ol/index.json
index a875830..fe70035 100644
--- a/test/fixtures/ol/index.json
+++ b/test/fixtures/ol/index.json
@@ -1,3 +1,5 @@
 {
+  "": "spread can’t be losslessly translated between HTML <> markdown",
+  "tree": false,
   "fragment": true
 }
diff --git a/test/fixtures/ol/index.md b/test/fixtures/ol/index.md
index 16f435a..6c4b2f6 100644
--- a/test/fixtures/ol/index.md
+++ b/test/fixtures/ol/index.md
@@ -1,5 +1,7 @@
 2.  Alpha
+
 3.  Bravo
+
 4.  ```js
     charlie();
     ```
@@ -27,23 +29,31 @@ Bar.
 Baz.
 
 1.
+
 2.  Something else
 
 Qux.
 
 1.  Something else
+
 2.
 
 Quux.
 
 1.  Something else
+
 2.
 
 Quuux.
 
 1.  [x] Bravo
+
 2.  [ ] Charlie
+
 3.  [x] Delta
+
 4.  [ ] Echo
+
 5.  [ ] **Foxtrot**
+
 6.  [ ] **Golf**
diff --git a/test/fixtures/ul/index.json b/test/fixtures/ul/index.json
index a875830..fe70035 100644
--- a/test/fixtures/ul/index.json
+++ b/test/fixtures/ul/index.json
@@ -1,3 +1,5 @@
 {
+  "": "spread can’t be losslessly translated between HTML <> markdown",
+  "tree": false,
   "fragment": true
 }
diff --git a/test/fixtures/ul/index.md b/test/fixtures/ul/index.md
index cc1d379..490718a 100644
--- a/test/fixtures/ul/index.md
+++ b/test/fixtures/ul/index.md
@@ -1,5 +1,7 @@
 *   Alpha
+
 *   Bravo
+
 *   ```js
     charlie();
     ```
@@ -27,23 +29,31 @@ Bar.
 Baz.
 
 *
+
 *   Something else
 
 Qux.
 
 *   Something else
+
 *
 
 Quux.
 
 *   Something else
+
 *
 
 Quuux.
 
 *   [x] Bravo
+
 *   [ ] Charlie
+
 *   [x] Delta
+
 *   [ ] Echo
+
 *   [ ] **Foxtrot**
+
 *   [ ] **Golf**