diff --git a/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/get-prev-list-depth.ts b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/get-prev-list-depth.ts
new file mode 100644
index 000000000..0a594ce64
--- /dev/null
+++ b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/get-prev-list-depth.ts
@@ -0,0 +1,30 @@
+import { EditorState } from "@tiptap/pm/state";
+import { findListItemPos } from "src/ui/extensions/custom-list-keymap/list-helpers/find-list-item-pos";
+
+export const getPrevListDepth = (typeOrName: string, state: EditorState) => {
+  const listItemPos = findListItemPos(typeOrName, state);
+
+  if (!listItemPos) {
+    return false;
+  }
+
+  let depth = -2;
+  let pos = listItemPos.$pos;
+
+  // Adjust the position to ensure we're within the list item, especially for edge cases
+  // This adjustment aims to more accurately reflect the document structure
+  let adjustedPos = pos;
+  // Adjusting the position by -3 to account for the off-by-three error
+  adjustedPos = state.doc.resolve(Math.max(adjustedPos.pos - 3, 0));
+
+  // Traverse up the document structure from the adjusted position
+  for (let d = adjustedPos.depth; d > 0; d--) {
+    const node = adjustedPos.node(d);
+    if (node.type.name === "bulletList" || node.type.name === "orderedList") {
+      depth++;
+    }
+  }
+
+  console.log("depth", depth);
+  return depth;
+};
diff --git a/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/handle-backspace.ts b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/handle-backspace.ts
index 885169aab..ee0a60757 100644
--- a/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/handle-backspace.ts
+++ b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/handle-backspace.ts
@@ -6,6 +6,9 @@ import { hasListBefore } from "src/ui/extensions/custom-list-keymap/list-helpers
 
 import { hasListItemBefore } from "src/ui/extensions/custom-list-keymap/list-helpers/has-list-item-before";
 import { listItemHasSubList } from "src/ui/extensions/custom-list-keymap/list-helpers/list-item-has-sub-list";
+import { isCursorInSubList } from "./is-sublist";
+import { nextListIsDeeper } from "./next-list-is-deeper";
+import { prevListIsHigher } from "./prev-list-is-deeper";
 
 export const handleBackspace = (editor: Editor, name: string, parentListTypes: string[]) => {
   // this is required to still handle the undo handling
@@ -61,18 +64,47 @@ export const handleBackspace = (editor: Editor, name: string, parentListTypes: s
   if (!listItemPos) {
     return false;
   }
+  const currentNode = listItemPos.$pos.node(listItemPos.depth);
+  const currentNodeSize = currentNode.nodeSize;
+  const currentListItemHasSubList = listItemHasSubList(name, editor.state, currentNode);
+  const isCurrentListItemSublist = prevListIsHigher(name, editor.state);
+  // __AUTO_GENERATED_PRINT_VAR_START__
+  console.log(
+    "handleBackspace isCurrentListItemSublist: %s",
+    isCurrentListItemSublist,
+    hasListItemBefore(name, editor.state)
+  ); // __AUTO_GENERATED_PRINT_VAR_END__
+  // if the cursor is not at the start of a node
+  // do nothing and proceed
+  if (!isAtStartOfNode(editor.state)) {
+    return false;
+  }
 
   const $prev = editor.state.doc.resolve(listItemPos.$pos.pos - 2);
   const prevNode = $prev.node(listItemPos.depth);
 
   const previousListItemHasSubList = listItemHasSubList(name, editor.state, prevNode);
-
-  // if the previous item is a list item and doesn't have a sublist, join the list items
-  if (hasListItemBefore(name, editor.state) && previousListItemHasSubList) {
-    return editor.chain().liftListItem(name).run();
-    // return editor.commands.joinItemBackward();
+  // if the previous item is a list item and has a sublist, join the list items (this scenario only occurs when a sublist's first item is lifted)
+  if (
+    // hasListItemBefore(name, editor.state) &&
+    // currentListItemHasSubList &&
+    // currentNodeSize > 4 &&
+    // !previousListItemHasSubList &&
+    isCurrentListItemSublist
+  ) {
+    console.log("ran 0");
+    editor.chain().liftListItem(name).run();
+    return editor.commands.joinItemBackward();
+    // return editor.chain().liftListItem(name).run();
   }
 
+  // if the previous item is a list item and doesn't have a sublist, join the list items
+  if (hasListItemBefore(name, editor.state)) {
+    console.log("ran 1");
+    return editor.chain().liftListItem(name).run();
+  }
+
+  console.log("ran 2");
   // otherwise in the end, a backspace should
   // always just lift the list item if
   // joining / merging is not possible
diff --git a/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/is-sublist.ts b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/is-sublist.ts
new file mode 100644
index 000000000..cb95e6fc1
--- /dev/null
+++ b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/is-sublist.ts
@@ -0,0 +1,26 @@
+import { Editor } from "@tiptap/core";
+
+export function isCursorInSubList(editor: Editor) {
+  const { selection } = editor.state;
+  const { $from } = selection;
+
+  // Check if the current node is a list item
+  const listItem = editor.schema.nodes.listItem;
+
+  // Traverse up the document tree from the current position
+  for (let depth = $from.depth; depth > 0; depth--) {
+    const node = $from.node(depth);
+    if (node.type === listItem) {
+      // If the parent of the list item is also a list, it's a sub-list
+      const parent = $from.node(depth - 1);
+      if (
+        parent &&
+        (parent.type === editor.schema.nodes.bulletList || parent.type === editor.schema.nodes.orderedList)
+      ) {
+        return true;
+      }
+    }
+  }
+
+  return false;
+}
diff --git a/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/prev-list-is-deeper.ts b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/prev-list-is-deeper.ts
new file mode 100644
index 000000000..51d790d20
--- /dev/null
+++ b/packages/editor/core/src/ui/extensions/custom-list-keymap/list-helpers/prev-list-is-deeper.ts
@@ -0,0 +1,20 @@
+import { EditorState } from "@tiptap/pm/state";
+
+import { findListItemPos } from "src/ui/extensions/custom-list-keymap/list-helpers/find-list-item-pos";
+import { getPrevListDepth } from "./get-prev-list-depth";
+
+export const prevListIsHigher = (typeOrName: string, state: EditorState) => {
+  const listDepth = getPrevListDepth(typeOrName, state);
+  const listItemPos = findListItemPos(typeOrName, state);
+
+  if (!listItemPos || !listDepth) {
+    return false;
+  }
+
+  console.log(listDepth, listItemPos.depth, listItemPos, listDepth < listItemPos.depth);
+  if (listDepth < listItemPos.depth) {
+    return true;
+  }
+
+  return false;
+};
diff --git a/packages/editor/core/src/ui/extensions/index.tsx b/packages/editor/core/src/ui/extensions/index.tsx
index a26fa2e3d..e329f3881 100644
--- a/packages/editor/core/src/ui/extensions/index.tsx
+++ b/packages/editor/core/src/ui/extensions/index.tsx
@@ -91,7 +91,6 @@ export const CoreEditorExtensions = (
   }),
   TiptapUnderline,
   TextStyle,
-  Color,
   TaskList.configure({
     HTMLAttributes: {
       class: "not-prose pl-2",
@@ -108,7 +107,6 @@ export const CoreEditorExtensions = (
   CustomCodeInlineExtension,
   Markdown.configure({
     html: true,
-    transformCopiedText: true,
     transformPastedText: true,
   }),
   Table,