diff --git a/.changeset/flat-berries-sell.md b/.changeset/flat-berries-sell.md
new file mode 100644
index 0000000000000..a46de3658945d
--- /dev/null
+++ b/.changeset/flat-berries-sell.md
@@ -0,0 +1,5 @@
+---
+'@rocket.chat/pdf-worker': patch
+---
+
+Fixes broken chat transcript when there are more than one file per message
diff --git a/ee/packages/pdf-worker/src/templates/ChatTranscript/ChatTranscript.fixtures.ts b/ee/packages/pdf-worker/src/templates/ChatTranscript/ChatTranscript.fixtures.ts
index f5cb16365f8be..157ec50b64fb5 100644
--- a/ee/packages/pdf-worker/src/templates/ChatTranscript/ChatTranscript.fixtures.ts
+++ b/ee/packages/pdf-worker/src/templates/ChatTranscript/ChatTranscript.fixtures.ts
@@ -154,7 +154,14 @@ export const exampleData: WorkerData = {
 				name: 'Christian Castro',
 				username: 'cristiano.castro',
 			},
-			files: [{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') }],
+			files: [
+				{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') },
+				{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') },
+				{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') },
+				{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') },
+				{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') },
+				{ name: 'screenshot.png', buffer: Buffer.from(base64Image, 'base64') },
+			],
 		},
 		{
 			msg: 'Thank you, I am checking on that for you now.',
diff --git a/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Files.tsx b/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Files.tsx
index 55831dce9c674..925a1733272c0 100644
--- a/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Files.tsx
+++ b/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Files.tsx
@@ -7,14 +7,22 @@ import { fontScales } from '@rocket.chat/fuselage-tokens/typography.json';
 import type { PDFFile } from '../../../types/ChatTranscriptData';
 
 const styles = StyleSheet.create({
+	container: {
+		marginTop: 8,
+		width: '100%',
+	},
 	file: {
 		color: colors.n700,
-		marginTop: 4,
+		marginBottom: 16,
 		flexDirection: 'column',
 		fontSize: fontScales.c1.fontSize,
+		width: '100%',
+	},
+	fileName: {
+		marginBottom: 6,
 	},
 	image: {
-		width: 400,
+		width: '100%',
 		maxHeight: 240,
 		objectFit: 'contain',
 		objectPosition: '0',
@@ -31,10 +39,10 @@ const styles = StyleSheet.create({
 });
 
 export const Files = ({ files, invalidMessage }: { files: PDFFile[]; invalidMessage: string }) => (
-	<View wrap={false}>
+	<View style={styles.container}>
 		{files?.map((file, index) => (
-			<View style={styles.file} key={index}>
-				<Text>{file.name}</Text>
+			<View style={styles.file} key={index} wrap>
+				<Text style={styles.fileName}>{file.name}</Text>
 				{file.buffer ? (
 					// Cache = false is required to avoid a bug in react-pdf
 					// Which causes the image to be duplicated when using buffers because of bad caching
diff --git a/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Message.tsx b/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Message.tsx
index 4228ea2e37396..11dd186d350c9 100644
--- a/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Message.tsx
+++ b/ee/packages/pdf-worker/src/templates/ChatTranscript/components/Message.tsx
@@ -52,7 +52,7 @@ const processMessage = (message: PDFMessage) => {
 };
 
 const Message = ({ message, invalidFileMessage }: { message: PDFMessage; invalidFileMessage: string }) => (
-	<View style={styles.wrapper} wrap={!!message.quotes || messageLongerThanPage(message.msg)}>
+	<View style={styles.wrapper} wrap={!!message.quotes || messageLongerThanPage(message.msg) || (message.files && message.files.length > 0)}>
 		{message.divider && <Divider divider={message.divider} />}
 		<MessageHeader name={message.u.name || message.u.username} time={message.ts} />