diff --git a/packages/core/src/commands/toggleList.ts b/packages/core/src/commands/toggleList.ts
index a912f7277..50c29ded1 100644
--- a/packages/core/src/commands/toggleList.ts
+++ b/packages/core/src/commands/toggleList.ts
@@ -1,9 +1,53 @@
 import { NodeType } from 'prosemirror-model'
+import { Transaction } from 'prosemirror-state'
+import { canJoin } from 'prosemirror-transform'
 import { RawCommands } from '../types'
 import { getNodeType } from '../helpers/getNodeType'
 import { findParentNode } from '../helpers/findParentNode'
 import { isList } from '../helpers/isList'
 
+const joinListBackwards = (tr: Transaction, listType: NodeType): boolean => {
+  const list = findParentNode(node => node.type === listType)(tr.selection)
+
+  if (!list) {
+    return true
+  }
+
+  const before = tr.doc.resolve(Math.max(0, list.pos - 1)).before(list.depth)
+  const nodeBefore = tr.doc.nodeAt(before)
+  const canJoinBackwards = list.node.type === nodeBefore?.type
+    && canJoin(tr.doc, list.pos)
+
+  if (!canJoinBackwards) {
+    return true
+  }
+
+  tr.join(list.pos)
+
+  return true
+}
+
+const joinListForwards = (tr: Transaction, listType: NodeType): boolean => {
+  const list = findParentNode(node => node.type === listType)(tr.selection)
+
+  if (!list) {
+    return true
+  }
+
+  const after = tr.doc.resolve(list.start).after(list.depth)
+  const nodeAfter = tr.doc.nodeAt(after)
+  const canJoinForwards = list.node.type === nodeAfter?.type
+    && canJoin(tr.doc, after)
+
+  if (!canJoinForwards) {
+    return true
+  }
+
+  tr.join(after)
+
+  return true
+}
+
 declare module '@tiptap/core' {
   interface Commands<ReturnType> {
     toggleList: {
@@ -43,21 +87,31 @@ export const toggleList: RawCommands['toggleList'] = (listTypeOrName, itemTypeOr
       && listType.validContent(parentList.node.content)
       && dispatch
     ) {
-      tr.setNodeMarkup(parentList.pos, listType)
+      return chain()
+        .command(() => {
+          tr.setNodeMarkup(parentList.pos, listType)
 
-      return true
+          return true
+        })
+        .command(() => joinListBackwards(tr, listType))
+        .command(() => joinListForwards(tr, listType))
+        .run()
     }
   }
 
-  const canWrapInList = can().wrapInList(listType)
+  return chain()
+    // try to convert node to default node if needed
+    .command(() => {
+      const canWrapInList = can().wrapInList(listType)
 
-  // try to convert node to paragraph if needed
-  if (!canWrapInList) {
-    return chain()
-      .clearNodes()
-      .wrapInList(listType)
-      .run()
-  }
+      if (canWrapInList) {
+        return true
+      }
 
-  return commands.wrapInList(listType)
+      return commands.clearNodes()
+    })
+    .wrapInList(listType)
+    .command(() => joinListBackwards(tr, listType))
+    .command(() => joinListForwards(tr, listType))
+    .run()
 }