diff --git a/api/models/Message.js b/api/models/Message.js
index ccff9cb48..0d807f6bf 100644
--- a/api/models/Message.js
+++ b/api/models/Message.js
@@ -73,15 +73,17 @@ async function saveMessage(req, params, metadata) {
  * @async
  * @function bulkSaveMessages
  * @param {Object[]} messages - An array of message objects to save.
+ * @param {boolean} [overrideTimestamp=false] - Indicates whether to override the timestamps of the messages. Defaults to false.
  * @returns {Promise<Object>} The result of the bulk write operation.
  * @throws {Error} If there is an error in saving messages in bulk.
  */
-async function bulkSaveMessages(messages) {
+async function bulkSaveMessages(messages, overrideTimestamp=false) {
   try {
     const bulkOps = messages.map((message) => ({
       updateOne: {
         filter: { messageId: message.messageId },
         update: message,
+        timestamps: !overrideTimestamp,
         upsert: true,
       },
     }));
diff --git a/api/models/convoStructure.spec.js b/api/models/convoStructure.spec.js
new file mode 100644
index 000000000..31c7eda24
--- /dev/null
+++ b/api/models/convoStructure.spec.js
@@ -0,0 +1,223 @@
+const mongoose = require('mongoose');
+const { MongoMemoryServer } = require('mongodb-memory-server');
+const { Message, getMessages, bulkSaveMessages } = require('./Message');
+
+// Original version of buildTree function
+function buildTree({ messages, fileMap }) {
+  if (messages === null) {
+    return null;
+  }
+
+  const messageMap = {};
+  const rootMessages = [];
+  const childrenCount = {};
+
+  messages.forEach((message) => {
+    const parentId = message.parentMessageId ?? '';
+    childrenCount[parentId] = (childrenCount[parentId] || 0) + 1;
+
+    const extendedMessage = {
+      ...message,
+      children: [],
+      depth: 0,
+      siblingIndex: childrenCount[parentId] - 1,
+    };
+
+    if (message.files && fileMap) {
+      extendedMessage.files = message.files.map((file) => fileMap[file.file_id ?? ''] ?? file);
+    }
+
+    messageMap[message.messageId] = extendedMessage;
+
+    const parentMessage = messageMap[parentId];
+    if (parentMessage) {
+      parentMessage.children.push(extendedMessage);
+      extendedMessage.depth = parentMessage.depth + 1;
+    } else {
+      rootMessages.push(extendedMessage);
+    }
+  });
+
+  return rootMessages;
+}
+
+let mongod;
+
+beforeAll(async () => {
+  mongod = await MongoMemoryServer.create();
+  const uri = mongod.getUri();
+  await mongoose.connect(uri);
+});
+
+afterAll(async () => {
+  await mongoose.disconnect();
+  await mongod.stop();
+});
+
+beforeEach(async () => {
+  await Message.deleteMany({});
+});
+
+describe('Conversation Structure Tests', () => {
+  test('Conversation folding/corrupting with inconsistent timestamps', async () => {
+    const userId = 'testUser';
+    const conversationId = 'testConversation';
+
+    // Create messages with inconsistent timestamps
+    const messages = [
+      {
+        messageId: 'message0',
+        parentMessageId: null,
+        text: 'Message 0',
+        createdAt: new Date('2023-01-01T00:00:00Z'),
+      },
+      {
+        messageId: 'message1',
+        parentMessageId: 'message0',
+        text: 'Message 1',
+        createdAt: new Date('2023-01-01T00:02:00Z'),
+      },
+      {
+        messageId: 'message2',
+        parentMessageId: 'message1',
+        text: 'Message 2',
+        createdAt: new Date('2023-01-01T00:01:00Z'),
+      }, // Note: Earlier than its parent
+      {
+        messageId: 'message3',
+        parentMessageId: 'message1',
+        text: 'Message 3',
+        createdAt: new Date('2023-01-01T00:03:00Z'),
+      },
+      {
+        messageId: 'message4',
+        parentMessageId: 'message2',
+        text: 'Message 4',
+        createdAt: new Date('2023-01-01T00:04:00Z'),
+      },
+    ];
+
+    // Add common properties to all messages
+    messages.forEach((msg) => {
+      msg.conversationId = conversationId;
+      msg.user = userId;
+      msg.isCreatedByUser = false;
+      msg.error = false;
+      msg.unfinished = false;
+    });
+
+    // Save messages with overrideTimestamp omitted (default is false)
+    await bulkSaveMessages(messages, true);
+
+    // Retrieve messages (this will sort by createdAt)
+    const retrievedMessages = await getMessages({ conversationId, user: userId });
+
+    // Build tree
+    const tree = buildTree({ messages: retrievedMessages });
+
+    // Check if the tree is incorrect (folded/corrupted)
+    expect(tree.length).toBeGreaterThan(1); // Should have multiple root messages, indicating corruption
+  });
+
+  test('Fix: Conversation structure maintained with more than 16 messages', async () => {
+    const userId = 'testUser';
+    const conversationId = 'testConversation';
+
+    // Create more than 16 messages
+    const messages = Array.from({ length: 20 }, (_, i) => ({
+      messageId: `message${i}`,
+      parentMessageId: i === 0 ? null : `message${i - 1}`,
+      conversationId,
+      user: userId,
+      text: `Message ${i}`,
+      createdAt: new Date(Date.now() + (i % 2 === 0 ? i * 500000 : -i * 500000)),
+    }));
+
+    // Save messages with new timestamps being generated (message objects ignored)
+    await bulkSaveMessages(messages);
+
+    // Retrieve messages (this will sort by createdAt, but it shouldn't matter now)
+    const retrievedMessages = await getMessages({ conversationId, user: userId });
+
+    // Build tree
+    const tree = buildTree({ messages: retrievedMessages });
+
+    // Check if the tree is correct
+    expect(tree.length).toBe(1); // Should have only one root message
+    let currentNode = tree[0];
+    for (let i = 1; i < 20; i++) {
+      expect(currentNode.children.length).toBe(1);
+      currentNode = currentNode.children[0];
+      expect(currentNode.text).toBe(`Message ${i}`);
+    }
+    expect(currentNode.children.length).toBe(0); // Last message should have no children
+  });
+
+  test('Simulate MongoDB ordering issue with more than 16 messages and close timestamps', async () => {
+    const userId = 'testUser';
+    const conversationId = 'testConversation';
+
+    // Create more than 16 messages with very close timestamps
+    const messages = Array.from({ length: 20 }, (_, i) => ({
+      messageId: `message${i}`,
+      parentMessageId: i === 0 ? null : `message${i - 1}`,
+      conversationId,
+      user: userId,
+      text: `Message ${i}`,
+      createdAt: new Date(Date.now() + (i % 2 === 0 ? i * 1 : -i * 1)),
+    }));
+
+    // Add common properties to all messages
+    messages.forEach((msg) => {
+      msg.isCreatedByUser = false;
+      msg.error = false;
+      msg.unfinished = false;
+    });
+
+    await bulkSaveMessages(messages, true);
+    const retrievedMessages = await getMessages({ conversationId, user: userId });
+    const tree = buildTree({ messages: retrievedMessages });
+    expect(tree.length).toBeGreaterThan(1);
+  });
+
+  test('Fix: Preserve order with more than 16 messages by maintaining original timestamps', async () => {
+    const userId = 'testUser';
+    const conversationId = 'testConversation';
+
+    // Create more than 16 messages with distinct timestamps
+    const messages = Array.from({ length: 20 }, (_, i) => ({
+      messageId: `message${i}`,
+      parentMessageId: i === 0 ? null : `message${i - 1}`,
+      conversationId,
+      user: userId,
+      text: `Message ${i}`,
+      createdAt: new Date(Date.now() + i * 1000), // Ensure each message has a distinct timestamp
+    }));
+
+    // Add common properties to all messages
+    messages.forEach((msg) => {
+      msg.isCreatedByUser = false;
+      msg.error = false;
+      msg.unfinished = false;
+    });
+
+    // Save messages with overriding timestamps (preserve original timestamps)
+    await bulkSaveMessages(messages, true);
+
+    // Retrieve messages (this will sort by createdAt)
+    const retrievedMessages = await getMessages({ conversationId, user: userId });
+
+    // Build tree
+    const tree = buildTree({ messages: retrievedMessages });
+
+    // Check if the tree is correct
+    expect(tree.length).toBe(1); // Should have only one root message
+    let currentNode = tree[0];
+    for (let i = 1; i < 20; i++) {
+      expect(currentNode.children.length).toBe(1);
+      currentNode = currentNode.children[0];
+      expect(currentNode.text).toBe(`Message ${i}`);
+    }
+    expect(currentNode.children.length).toBe(0); // Last message should have no children
+  });
+});
diff --git a/api/server/utils/import/fork.spec.js b/api/server/utils/import/fork.spec.js
index f4f4a2b81..003f83ab2 100644
--- a/api/server/utils/import/fork.spec.js
+++ b/api/server/utils/import/fork.spec.js
@@ -104,7 +104,7 @@ describe('forkConversation', () => {
     expect(bulkSaveMessages).toHaveBeenCalledWith(
       expect.arrayContaining(
         expectedMessagesTexts.map((text) => expect.objectContaining({ text })),
-      ),
+      ), true,
     );
   });
 
@@ -122,7 +122,7 @@ describe('forkConversation', () => {
     expect(bulkSaveMessages).toHaveBeenCalledWith(
       expect.arrayContaining(
         expectedMessagesTexts.map((text) => expect.objectContaining({ text })),
-      ),
+      ), true,
     );
   });
 
@@ -141,7 +141,7 @@ describe('forkConversation', () => {
     expect(bulkSaveMessages).toHaveBeenCalledWith(
       expect.arrayContaining(
         expectedMessagesTexts.map((text) => expect.objectContaining({ text })),
-      ),
+      ), true,
     );
   });
 
@@ -160,7 +160,7 @@ describe('forkConversation', () => {
     expect(bulkSaveMessages).toHaveBeenCalledWith(
       expect.arrayContaining(
         expectedMessagesTexts.map((text) => expect.objectContaining({ text })),
-      ),
+      ), true,
     );
   });
 
diff --git a/api/server/utils/import/importBatchBuilder.js b/api/server/utils/import/importBatchBuilder.js
index 16b4f0ffd..f42e675eb 100644
--- a/api/server/utils/import/importBatchBuilder.js
+++ b/api/server/utils/import/importBatchBuilder.js
@@ -99,7 +99,7 @@ class ImportBatchBuilder {
   async saveBatch() {
     try {
       await bulkSaveConvos(this.conversations);
-      await bulkSaveMessages(this.messages);
+      await bulkSaveMessages(this.messages, true);
       logger.debug(
         `user: ${this.requestUserId} | Added ${this.conversations.length} conversations and ${this.messages.length} messages to the DB.`,
       );
diff --git a/client/src/components/Chat/Messages/SearchMessage.tsx b/client/src/components/Chat/Messages/SearchMessage.tsx
index ceaf1415a..c26d3bd07 100644
--- a/client/src/components/Chat/Messages/SearchMessage.tsx
+++ b/client/src/components/Chat/Messages/SearchMessage.tsx
@@ -24,10 +24,10 @@ export default function Message({ message }: Pick<TMessageProps, 'message'>) {
   let messageLabel = '';
   if (isCreatedByUser) {
     messageLabel = UsernameDisplay
-      ? (user?.name ?? '') || user?.username
+      ? (user?.name ?? '') || (user?.username ?? '')
       : localize('com_user_message');
   } else {
-    messageLabel = message.sender;
+    messageLabel = message.sender || '';
   }
 
   return (
diff --git a/client/src/components/Share/Message.tsx b/client/src/components/Share/Message.tsx
index 34f095a92..7bc112ba8 100644
--- a/client/src/components/Share/Message.tsx
+++ b/client/src/components/Share/Message.tsx
@@ -28,13 +28,20 @@ export default function Message(props: TMessageProps) {
     return null;
   }
 
-  const { text, children, messageId = null, isCreatedByUser, error, unfinished } = message ?? {};
+  const {
+    text = '',
+    children,
+    messageId = null,
+    isCreatedByUser = true,
+    error = false,
+    unfinished = false,
+  } = message;
 
   let messageLabel = '';
   if (isCreatedByUser) {
     messageLabel = 'anonymous';
   } else {
-    messageLabel = message.sender;
+    messageLabel = message.sender || '';
   }
 
   return (
@@ -67,12 +74,12 @@ export default function Message(props: TMessageProps) {
                       error={error}
                       isLast={false}
                       ask={() => ({})}
-                      text={text ?? ''}
+                      text={text}
                       message={message}
                       isSubmitting={false}
                       enterEdit={() => ({})}
                       unfinished={!!unfinished}
-                      isCreatedByUser={isCreatedByUser ?? true}
+                      isCreatedByUser={isCreatedByUser}
                       siblingIdx={siblingIdx ?? 0}
                       setSiblingIdx={setSiblingIdx ?? (() => ({}))}
                     />
diff --git a/client/src/hooks/Conversations/useExportConversation.ts b/client/src/hooks/Conversations/useExportConversation.ts
index a1291f940..68c2061c2 100644
--- a/client/src/hooks/Conversations/useExportConversation.ts
+++ b/client/src/hooks/Conversations/useExportConversation.ts
@@ -67,11 +67,11 @@ export default function useExportConversation({
     };
 
     if (!message.content) {
-      return formatText(message.sender, message.text);
+      return formatText(message.sender || '', message.text);
     }
 
     return message.content
-      .map((content) => getMessageContent(message.sender, content))
+      .map((content) => getMessageContent(message.sender || '', content))
       .map((text) => {
         return formatText(text[0], text[1]);
       })
diff --git a/packages/data-provider/src/schemas.ts b/packages/data-provider/src/schemas.ts
index cef29a8cc..dd23b9aa7 100644
--- a/packages/data-provider/src/schemas.ts
+++ b/packages/data-provider/src/schemas.ts
@@ -445,12 +445,12 @@ export const tMessageSchema = z.object({
   bg: z.string().nullable().optional(),
   model: z.string().nullable().optional(),
   title: z.string().nullable().or(z.literal('New Chat')).default('New Chat'),
-  sender: z.string(),
+  sender: z.string().optional(),
   text: z.string(),
   generation: z.string().nullable().optional(),
   isEdited: z.boolean().optional(),
   isCreatedByUser: z.boolean(),
-  error: z.boolean(),
+  error: z.boolean().optional(),
   createdAt: z
     .string()
     .optional()