diff --git a/app/src/protyle/util/editorCommonEvent.ts b/app/src/protyle/util/editorCommonEvent.ts
index 1a7193ed6..5db2200fa 100644
--- a/app/src/protyle/util/editorCommonEvent.ts
+++ b/app/src/protyle/util/editorCommonEvent.ts
@@ -284,6 +284,18 @@ const moveTo = async (protyle: IProtyle, sourceElements: Element[], targetElemen
 const dragSb = async (protyle: IProtyle, sourceElements: Element[], targetElement: Element, isBottom: boolean,
                       direct: "col" | "row", isCopy: boolean) => {
     const isSameDoc = protyle.element.contains(sourceElements[0]);
+    // 把列表块中的唯一一个列表项块拖拽到列表块的左侧 https://github.com/siyuan-note/siyuan/issues/16315
+    if (isSameDoc && sourceElements[0].classList.contains("li") && targetElement === sourceElements[0].parentElement &&
+        targetElement.childElementCount === sourceElements.length + 1) {
+        const outLiElement = sourceElements.find((element) => {
+            if (!targetElement.contains(element)) {
+                return true;
+            }
+        });
+        if (!outLiElement) {
+            return;
+        }
+    }
     const undoOperations: IOperation[] = [];
     const targetMoveUndo: IOperation = {
         action: "move",
diff --git a/app/src/protyle/wysiwyg/getBlock.ts b/app/src/protyle/wysiwyg/getBlock.ts
index 5985ccd69..f445dfcb5 100644
--- a/app/src/protyle/wysiwyg/getBlock.ts
+++ b/app/src/protyle/wysiwyg/getBlock.ts
@@ -118,7 +118,7 @@ export const getTopEmptyElement = (element: Element) => {
 
 export const getTopAloneElement = (topSourceElement: Element) => {
     if ("NodeBlockquote" === topSourceElement.parentElement.getAttribute("data-type") && topSourceElement.parentElement.childElementCount === 2) {
-        while (!topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
+        while (topSourceElement.parentElement && !topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
             if (topSourceElement.parentElement.getAttribute("data-type") === "NodeBlockquote" && topSourceElement.parentElement.childElementCount === 2) {
                 topSourceElement = topSourceElement.parentElement;
             } else {
@@ -127,7 +127,7 @@ export const getTopAloneElement = (topSourceElement: Element) => {
             }
         }
     } else if ("NodeSuperBlock" === topSourceElement.parentElement.getAttribute("data-type") && topSourceElement.parentElement.childElementCount === 2) {
-        while (!topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
+        while (topSourceElement.parentElement && !topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
             if (topSourceElement.parentElement.getAttribute("data-type") === "NodeSuperBlock" && topSourceElement.parentElement.childElementCount === 2) {
                 topSourceElement = topSourceElement.parentElement;
             } else {
@@ -136,7 +136,7 @@ export const getTopAloneElement = (topSourceElement: Element) => {
             }
         }
     } else if ("NodeListItem" === topSourceElement.parentElement.getAttribute("data-type") && topSourceElement.parentElement.childElementCount === 3) {
-        while (!topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
+        while (topSourceElement.parentElement && !topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
             if (topSourceElement.parentElement.getAttribute("data-type") === "NodeListItem" && topSourceElement.parentElement.childElementCount === 3) {
                 topSourceElement = topSourceElement.parentElement;
             } else if (topSourceElement.parentElement.getAttribute("data-type") === "NodeList" && topSourceElement.parentElement.childElementCount === 2) {
@@ -147,7 +147,7 @@ export const getTopAloneElement = (topSourceElement: Element) => {
             }
         }
     } else if ("NodeList" === topSourceElement.parentElement.getAttribute("data-type") && topSourceElement.parentElement.childElementCount === 2) {
-        while (!topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
+        while (topSourceElement.parentElement && !topSourceElement.parentElement.classList.contains("protyle-wysiwyg")) {
             if ("NodeList" === topSourceElement.parentElement.getAttribute("data-type") && topSourceElement.parentElement.childElementCount === 2) {
                 topSourceElement = topSourceElement.parentElement;
             } else if (topSourceElement.parentElement.getAttribute("data-type") === "NodeListItem" && topSourceElement.parentElement.childElementCount === 3) {