diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts b/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts
index 9e51d5a6f5c..727179577cf 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts
@@ -685,6 +685,14 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		templateData.currentElement = element;
 		this.templateDataByRequestId.set(element.id, templateData);
 
+		// Clear pending-related classes and drag handle from previous renders
+		// Do this before element-type checks to ensure dividers also get cleaned up
+		templateData.rowContainer.classList.remove('pending-item', 'pending-divider', 'pending-request', 'chat-pending-dragging');
+		templateData.dragHandle?.remove();
+		templateData.dragHandle = undefined;
+		delete templateData.rowContainer.dataset.pendingRequestId;
+		delete templateData.rowContainer.dataset.pendingKind;
+
 		// Handle pending divider with simplified rendering
 		if (isPendingDividerVM(element)) {
 			this.renderPendingDivider(element, templateData);
@@ -730,12 +738,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		templateData.rowContainer.classList.toggle('editing-session', location === ChatAgentLocation.Chat);
 		templateData.rowContainer.classList.toggle('interactive-request', isRequestVM(element));
 		templateData.rowContainer.classList.toggle('interactive-response', isResponseVM(element));
-		// Clear pending-related classes and drag handle from previous renders
-		templateData.rowContainer.classList.remove('pending-item', 'pending-divider', 'pending-request');
-		templateData.dragHandle?.remove();
-		templateData.dragHandle = undefined;
-		delete templateData.rowContainer.dataset.pendingRequestId;
-		delete templateData.rowContainer.dataset.pendingKind;
 		const progressMessageAtBottomOfResponse = checkModeOption(this.delegate.currentChatMode(), this.rendererOptions.progressMessageAtBottomOfResponse);
 		templateData.rowContainer.classList.toggle('show-detail-progress', isResponseVM(element) && !element.isComplete && !element.progressMessages.length && !progressMessageAtBottomOfResponse);
 		if (!this.rendererOptions.noHeader) {