diff --git a/src/lib/utils/index.ts b/src/lib/utils/index.ts
index dc23620a12..38e7636e25 100644
--- a/src/lib/utils/index.ts
+++ b/src/lib/utils/index.ts
@@ -677,7 +677,9 @@ export const calculateSHA256 = async (file) => {
 
 export const getImportOrigin = (_chats) => {
 	// Check what external service chat imports are from
-	if ('mapping' in _chats[0]) {
+	// ChatGPT exports may include folder/project metadata entries without 'mapping',
+	// so we check if ANY item has a 'mapping' key instead of only the first one.
+	if (_chats.some((chat) => 'mapping' in chat)) {
 		return 'openai';
 	}
 	return 'webui';
@@ -706,6 +708,21 @@ export const getUserPosition = async (raw = false) => {
 	}
 };
 
+const extractOpenAIMessageContent = (message): string => {
+	// Extract text content from a ChatGPT message, handling various content formats
+	// (string parts, object parts like DALL-E images, text field fallback)
+	try {
+		const parts = message?.['content']?.['parts'];
+		if (Array.isArray(parts)) {
+			const textParts = parts.filter((p) => typeof p === 'string');
+			if (textParts.length > 0) return textParts.join('\n');
+		}
+		return message?.['content']?.['text'] || '';
+	} catch {
+		return '';
+	}
+};
+
 const convertOpenAIMessages = (convo) => {
 	// Parse OpenAI chat messages and create chat dictionary for creating new chats
 	const mapping = convo['mapping'];
@@ -726,15 +743,18 @@ const convertOpenAIMessages = (convo) => {
 				// Skip chat messages with no content
 				continue;
 			} else {
+				const role = message['message']?.['author']?.['role'];
+				// Skip system and tool messages — they don't map to user/assistant
+				if (role === 'system' || role === 'tool') {
+					continue;
+				}
+
 				const new_chat = {
 					id: message_id,
 					parentId: lastId,
 					childrenIds: message['children'] || [],
-					role: message['message']?.['author']?.['role'] !== 'user' ? 'assistant' : 'user',
-					content:
-						message['message']?.['content']?.['parts']?.[0] ||
-						message['message']?.['content']?.['text'] ||
-						'',
+					role: role !== 'user' ? 'assistant' : 'user',
+					content: extractOpenAIMessageContent(message['message']),
 					model: 'gpt-3.5-turbo',
 					done: true,
 					context: null
@@ -747,6 +767,12 @@ const convertOpenAIMessages = (convo) => {
 		}
 	}
 
+	// Fix up the last message's childrenIds to be empty (it's the leaf node in our
+	// linear chain regardless of what the original tree structure had)
+	if (messages.length > 0) {
+		messages[messages.length - 1].childrenIds = [];
+	}
+
 	const history: Record<PropertyKey, (typeof messages)[number]> = {};
 	messages.forEach((obj) => (history[obj.id] = obj));
 
@@ -773,18 +799,6 @@ const validateChat = (chat) => {
 		return false;
 	}
 
-	// Last message's children should be an empty array
-	const lastMessage = messages[messages.length - 1];
-	if (lastMessage.childrenIds.length !== 0) {
-		return false;
-	}
-
-	// First message's parent should be null
-	const firstMessage = messages[0];
-	if (firstMessage.parentId !== null) {
-		return false;
-	}
-
 	// Every message's content should be a string
 	for (const message of messages) {
 		if (typeof message.content !== 'string') {
@@ -799,7 +813,15 @@ export const convertOpenAIChats = (_chats) => {
 	// Create a list of dictionaries with each conversation from import
 	const chats = [];
 	let failed = 0;
+	let skipped = 0;
 	for (const convo of _chats) {
+		// Skip folder/project metadata entries that lack a 'mapping' key
+		if (!('mapping' in convo)) {
+			skipped++;
+			console.log('Skipping non-conversation entry (folder/project):', convo['title'] ?? convo['id']);
+			continue;
+		}
+
 		const chat = convertOpenAIMessages(convo);
 
 		if (validateChat(chat)) {
@@ -815,6 +837,9 @@ export const convertOpenAIChats = (_chats) => {
 		}
 	}
 	console.log(failed, 'Conversations could not be imported');
+	if (skipped > 0) {
+		console.log(skipped, 'Non-conversation entries (folders/projects) were skipped');
+	}
 	return chats;
 };