diff --git a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentPreview.svelte b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentPreview.svelte
index 015f6fc3d7..fa01075496 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentPreview.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentPreview.svelte
@@ -1,12 +1,9 @@
 <script lang="ts">
 	import { Button } from '$lib/components/ui/button';
 	import { FileText, Image, Music, FileIcon, Eye } from '@lucide/svelte';
-	import { FileTypeCategory, MimeTypeApplication } from '$lib/enums/files';
-	import { ModelModality } from '$lib/enums/model';
-	import { AttachmentType } from '$lib/enums/attachment';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 	import { convertPDFToImage } from '$lib/utils/pdf-processing';
-	import { getFileTypeCategory } from '$lib/utils/file-type';
+	import { isTextFile, isImageFile, isPdfFile, isAudioFile } from '$lib/utils/attachment-type';
 
 	interface Props {
 		// Either an uploaded file or a stored attachment
@@ -15,55 +12,27 @@
 		// For uploaded files
 		preview?: string;
 		name?: string;
-		type?: string;
 		textContent?: string;
 	}
 
-	let { uploadedFile, attachment, preview, name, type, textContent }: Props = $props();
+	let { uploadedFile, attachment, preview, name, textContent }: Props = $props();
 
 	let displayName = $derived(uploadedFile?.name || attachment?.name || name || 'Unknown File');
 
+	// Determine file type from uploaded file or attachment
+	let isAudio = $derived(isAudioFile(attachment, uploadedFile));
+	let isImage = $derived(isImageFile(attachment, uploadedFile));
+	let isPdf = $derived(isPdfFile(attachment, uploadedFile));
+	let isText = $derived(isTextFile(attachment, uploadedFile));
+
 	let displayPreview = $derived(
 		uploadedFile?.preview ||
-			(attachment?.type === AttachmentType.IMAGE ? attachment.base64Url : preview)
-	);
-
-	let displayType = $derived(
-		uploadedFile
-			? uploadedFile.type
-			: attachment?.type === AttachmentType.IMAGE
-				? 'image'
-				: attachment?.type === AttachmentType.TEXT
-					? 'text'
-					: attachment?.type === AttachmentType.AUDIO
-						? attachment.mimeType || ModelModality.AUDIO
-						: attachment?.type === AttachmentType.PDF
-							? MimeTypeApplication.PDF
-							: type || 'unknown'
+			(isImage && attachment && 'base64Url' in attachment ? attachment.base64Url : preview)
 	);
 
 	let displayTextContent = $derived(
 		uploadedFile?.textContent ||
-			(attachment?.type === AttachmentType.TEXT
-				? attachment.content
-				: attachment?.type === AttachmentType.PDF
-					? attachment.content
-					: textContent)
-	);
-
-	let isAudio = $derived(
-		getFileTypeCategory(displayType) === FileTypeCategory.AUDIO ||
-			displayType === ModelModality.AUDIO
-	);
-
-	let isImage = $derived(
-		getFileTypeCategory(displayType) === FileTypeCategory.IMAGE || displayType === 'image'
-	);
-
-	let isPdf = $derived(displayType === MimeTypeApplication.PDF);
-
-	let isText = $derived(
-		getFileTypeCategory(displayType) === FileTypeCategory.TEXT || displayType === 'text'
+			(attachment && 'content' in attachment ? attachment.content : textContent)
 	);
 
 	let IconComponent = $derived(() => {
@@ -93,15 +62,20 @@
 
 			if (uploadedFile?.file) {
 				file = uploadedFile.file;
-			} else if (attachment?.type === AttachmentType.PDF) {
+			} else if (isPdf && attachment) {
 				// Check if we have pre-processed images
-				if (attachment.images && Array.isArray(attachment.images) && attachment.images.length > 0) {
+				if (
+					'images' in attachment &&
+					attachment.images &&
+					Array.isArray(attachment.images) &&
+					attachment.images.length > 0
+				) {
 					pdfImages = attachment.images;
 					return;
 				}
 
 				// Convert base64 back to File for processing
-				if (attachment.base64Data) {
+				if ('base64Data' in attachment && attachment.base64Data) {
 					const base64Data = attachment.base64Data;
 					const byteCharacters = atob(base64Data);
 					const byteNumbers = new Array(byteCharacters.length);
@@ -109,7 +83,7 @@
 						byteNumbers[i] = byteCharacters.charCodeAt(i);
 					}
 					const byteArray = new Uint8Array(byteNumbers);
-					file = new File([byteArray], displayName, { type: MimeTypeApplication.PDF });
+					file = new File([byteArray], displayName, { type: 'application/pdf' });
 				}
 			}
 
@@ -243,18 +217,18 @@
 				<div class="w-full max-w-md text-center">
 					<Music class="mx-auto mb-4 h-16 w-16 text-muted-foreground" />
 
-					{#if attachment?.type === AttachmentType.AUDIO}
+					{#if uploadedFile?.preview}
+						<audio controls class="mb-4 w-full" src={uploadedFile.preview}>
+							Your browser does not support the audio element.
+						</audio>
+					{:else if isAudio && attachment && 'mimeType' in attachment && 'base64Data' in attachment}
 						<audio
 							controls
 							class="mb-4 w-full"
-							src="data:{attachment.mimeType};base64,{attachment.base64Data}"
+							src={`data:${attachment.mimeType};base64,${attachment.base64Data}`}
 						>
 							Your browser does not support the audio element.
 						</audio>
-					{:else if uploadedFile?.preview}
-						<audio controls class="mb-4 w-full" src={uploadedFile.preview}>
-							Your browser does not support the audio element.
-						</audio>
 					{:else}
 						<p class="mb-4 text-muted-foreground">Audio preview not available</p>
 					{/if}
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentThumbnailFile.svelte b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentThumbnailFile.svelte
index 46f0d0007c..f7aeeeac16 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentThumbnailFile.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentThumbnailFile.svelte
@@ -1,7 +1,8 @@
 <script lang="ts">
 	import { RemoveButton } from '$lib/components/app';
 	import { formatFileSize, getFileTypeLabel, getPreviewText } from '$lib/utils/file-preview';
-	import { FileTypeCategory, MimeTypeText } from '$lib/enums/files';
+	import { isTextFile } from '$lib/utils/attachment-type';
+	import type { DatabaseMessageExtra } from '$lib/types/database';
 
 	interface Props {
 		class?: string;
@@ -12,7 +13,9 @@
 		readonly?: boolean;
 		size?: number;
 		textContent?: string;
-		type: string;
+		// Either uploaded file or stored attachment
+		uploadedFile?: ChatUploadedFile;
+		attachment?: DatabaseMessageExtra;
 	}
 
 	let {
@@ -24,11 +27,17 @@
 		readonly = false,
 		size,
 		textContent,
-		type
+		uploadedFile,
+		attachment
 	}: Props = $props();
+
+	let isText = $derived(isTextFile(attachment, uploadedFile));
+
+	// Get file type for display
+	let fileType = $derived(uploadedFile?.type || 'unknown');
 </script>
 
-{#if type === MimeTypeText.PLAIN || type === FileTypeCategory.TEXT}
+{#if isText}
 	{#if readonly}
 		<!-- Readonly mode (ChatMessage) -->
 		<button
@@ -45,7 +54,7 @@
 						<span class="text-xs text-muted-foreground">{formatFileSize(size)}</span>
 					{/if}
 
-					{#if textContent && type === 'text'}
+					{#if textContent}
 						<div class="relative mt-2 w-full">
 							<div
 								class="overflow-hidden font-mono text-xs leading-relaxed break-words whitespace-pre-wrap text-muted-foreground"
@@ -105,7 +114,7 @@
 		<div
 			class="flex h-8 w-8 items-center justify-center rounded bg-primary/10 text-xs font-medium text-primary"
 		>
-			{getFileTypeLabel(type)}
+			{getFileTypeLabel(fileType)}
 		</div>
 
 		<div class="flex flex-col gap-1">
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsList.svelte b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsList.svelte
index 425c5d34d9..4407cc30ae 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsList.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsList.svelte
@@ -4,8 +4,7 @@
 	import { ChevronLeft, ChevronRight } from '@lucide/svelte';
 	import { getFileTypeCategory } from '$lib/utils/file-type';
 	import { FileTypeCategory } from '$lib/enums/files';
-	import { ModelModality } from '$lib/enums/model';
-	import { AttachmentType } from '$lib/enums/attachment';
+	import { isImageFile } from '$lib/utils/attachment-type';
 	import { DialogChatAttachmentPreview, DialogChatAttachmentsViewAll } from '$lib/components/app';
 	import type { ChatAttachmentDisplayItem, ChatAttachmentPreviewItem } from '$lib/types/chat';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
@@ -62,7 +61,6 @@
 				name: file.name,
 				size: file.size,
 				preview: file.preview,
-				type: file.type,
 				isImage: getFileTypeCategory(file.type) === FileTypeCategory.IMAGE,
 				uploadedFile: file,
 				textContent: file.textContent
@@ -71,56 +69,17 @@
 
 		// Add stored attachments (ChatMessage)
 		for (const [index, attachment] of attachments.entries()) {
-			if (attachment.type === AttachmentType.IMAGE) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					preview: attachment.base64Url,
-					type: 'image',
-					isImage: true,
-					attachment,
-					attachmentIndex: index
-				});
-			} else if (attachment.type === AttachmentType.TEXT) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: 'text',
-					isImage: false,
-					attachment,
-					attachmentIndex: index,
-					textContent: attachment.content
-				});
-			} else if (attachment.type === AttachmentType.AUDIO) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: attachment.mimeType || ModelModality.AUDIO,
-					isImage: false,
-					attachment,
-					attachmentIndex: index
-				});
-			} else if (attachment.type === AttachmentType.PDF) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: 'application/pdf',
-					isImage: false,
-					attachment,
-					attachmentIndex: index
-				});
-			} else if (attachment.type === AttachmentType.LEGACY_CONTEXT) {
-				// Legacy format from old webui - treat as text file
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: 'text',
-					isImage: false,
-					attachment,
-					attachmentIndex: index,
-					textContent: attachment.content
-				});
-			}
+			const isImage = isImageFile(attachment);
+
+			items.push({
+				id: `attachment-${index}`,
+				name: attachment.name,
+				preview: isImage && 'base64Url' in attachment ? attachment.base64Url : undefined,
+				isImage,
+				attachment,
+				attachmentIndex: index,
+				textContent: 'content' in attachment ? attachment.content : undefined
+			});
 		}
 
 		return items.reverse();
@@ -135,7 +94,6 @@
 			attachment: item.attachment,
 			preview: item.preview,
 			name: item.name,
-			type: item.type,
 			size: item.size,
 			textContent: item.textContent
 		};
@@ -223,11 +181,12 @@
 									: ''}"
 								id={item.id}
 								name={item.name}
-								type={item.type}
 								size={item.size}
 								{readonly}
 								onRemove={onFileRemove}
 								textContent={item.textContent}
+								attachment={item.attachment}
+								uploadedFile={item.uploadedFile}
 								onClick={(event) => openPreview(item, event)}
 							/>
 						{/if}
@@ -279,12 +238,13 @@
 							class="cursor-pointer"
 							id={item.id}
 							name={item.name}
-							type={item.type}
 							size={item.size}
 							{readonly}
 							onRemove={onFileRemove}
 							textContent={item.textContent}
-							onClick={(event) => openPreview(item, event)}
+							attachment={item.attachment}
+							uploadedFile={item.uploadedFile}
+							onClick={(event?: MouseEvent) => openPreview(item, event)}
 						/>
 					{/if}
 				{/each}
@@ -300,7 +260,6 @@
 		attachment={previewItem.attachment}
 		preview={previewItem.preview}
 		name={previewItem.name}
-		type={previewItem.type}
 		size={previewItem.size}
 		textContent={previewItem.textContent}
 	/>
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
index a44b413ea1..f83197d4f0 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
@@ -5,9 +5,8 @@
 		DialogChatAttachmentPreview
 	} from '$lib/components/app';
 	import { FileTypeCategory } from '$lib/enums/files';
-	import { ModelModality } from '$lib/enums/model';
-	import { AttachmentType } from '$lib/enums/attachment';
 	import { getFileTypeCategory } from '$lib/utils/file-type';
+	import { isImageFile } from '$lib/utils/attachment-type';
 	import type { ChatAttachmentDisplayItem, ChatAttachmentPreviewItem } from '$lib/types/chat';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 
@@ -47,7 +46,6 @@
 				name: file.name,
 				size: file.size,
 				preview: file.preview,
-				type: file.type,
 				isImage: getFileTypeCategory(file.type) === FileTypeCategory.IMAGE,
 				uploadedFile: file,
 				textContent: file.textContent
@@ -55,56 +53,17 @@
 		}
 
 		for (const [index, attachment] of attachments.entries()) {
-			if (attachment.type === AttachmentType.IMAGE) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					preview: attachment.base64Url,
-					type: 'image',
-					isImage: true,
-					attachment,
-					attachmentIndex: index
-				});
-			} else if (attachment.type === AttachmentType.TEXT) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: 'text',
-					isImage: false,
-					attachment,
-					attachmentIndex: index,
-					textContent: attachment.content
-				});
-			} else if (attachment.type === AttachmentType.AUDIO) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: attachment.mimeType || ModelModality.AUDIO,
-					isImage: false,
-					attachment,
-					attachmentIndex: index
-				});
-			} else if (attachment.type === AttachmentType.PDF) {
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: 'application/pdf',
-					isImage: false,
-					attachment,
-					attachmentIndex: index
-				});
-			} else if (attachment.type === AttachmentType.LEGACY_CONTEXT) {
-				// Legacy format from old webui - treat as text file
-				items.push({
-					id: `attachment-${index}`,
-					name: attachment.name,
-					type: 'text',
-					isImage: false,
-					attachment,
-					attachmentIndex: index,
-					textContent: attachment.content
-				});
-			}
+			const isImage = isImageFile(attachment);
+
+			items.push({
+				id: `attachment-${index}`,
+				name: attachment.name,
+				preview: isImage && 'base64Url' in attachment ? attachment.base64Url : undefined,
+				isImage,
+				attachment,
+				attachmentIndex: index,
+				textContent: 'content' in attachment ? attachment.content : undefined
+			});
 		}
 
 		return items.reverse();
@@ -121,7 +80,6 @@
 			attachment: item.attachment,
 			preview: item.preview,
 			name: item.name,
-			type: item.type,
 			size: item.size,
 			textContent: item.textContent
 		};
@@ -140,12 +98,13 @@
 							class="cursor-pointer"
 							id={item.id}
 							name={item.name}
-							type={item.type}
 							size={item.size}
 							{readonly}
 							onRemove={onFileRemove}
 							textContent={item.textContent}
-							onClick={(event) => openPreview(item, event)}
+							attachment={item.attachment}
+							uploadedFile={item.uploadedFile}
+							onClick={(event?: MouseEvent) => openPreview(item, event)}
 						/>
 					{/each}
 				</div>
@@ -185,7 +144,6 @@
 		attachment={previewItem.attachment}
 		preview={previewItem.preview}
 		name={previewItem.name}
-		type={previewItem.type}
 		size={previewItem.size}
 		textContent={previewItem.textContent}
 	/>
diff --git a/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentPreview.svelte b/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentPreview.svelte
index f750fb2171..70e2758d2b 100644
--- a/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentPreview.svelte
+++ b/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentPreview.svelte
@@ -1,10 +1,9 @@
 <script lang="ts">
 	import * as Dialog from '$lib/components/ui/dialog';
-	import { ModelModality } from '$lib/enums/model';
-	import { AttachmentType } from '$lib/enums/attachment';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 	import { ChatAttachmentPreview } from '$lib/components/app';
 	import { formatFileSize } from '$lib/utils/file-preview';
+	import { getAttachmentTypeLabel } from '$lib/utils/attachment-type';
 
 	interface Props {
 		open: boolean;
@@ -15,7 +14,6 @@
 		// For uploaded files
 		preview?: string;
 		name?: string;
-		type?: string;
 		size?: number;
 		textContent?: string;
 	}
@@ -27,7 +25,6 @@
 		attachment,
 		preview,
 		name,
-		type,
 		size,
 		textContent
 	}: Props = $props();
@@ -36,22 +33,10 @@
 
 	let displayName = $derived(uploadedFile?.name || attachment?.name || name || 'Unknown File');
 
-	let displayType = $derived(
-		uploadedFile
-			? uploadedFile.type
-			: attachment?.type === AttachmentType.IMAGE
-				? 'image'
-				: attachment?.type === AttachmentType.TEXT
-					? 'text'
-					: attachment?.type === AttachmentType.AUDIO
-						? attachment.mimeType || ModelModality.AUDIO
-						: attachment?.type === AttachmentType.PDF
-							? 'application/pdf'
-							: type || 'unknown'
-	);
-
 	let displaySize = $derived(uploadedFile?.size || size);
 
+	let typeLabel = $derived(getAttachmentTypeLabel(uploadedFile, attachment));
+
 	$effect(() => {
 		if (open && chatAttachmentPreviewRef) {
 			chatAttachmentPreviewRef.reset();
@@ -62,9 +47,9 @@
 <Dialog.Root bind:open {onOpenChange}>
 	<Dialog.Content class="grid max-h-[90vh] max-w-5xl overflow-hidden sm:w-auto sm:max-w-6xl">
 		<Dialog.Header>
-			<Dialog.Title>{displayName}</Dialog.Title>
+			<Dialog.Title class="pr-8">{displayName}</Dialog.Title>
 			<Dialog.Description>
-				{displayType}
+				{typeLabel}
 				{#if displaySize}
 					• {formatFileSize(displaySize)}
 				{/if}
@@ -76,8 +61,7 @@
 			{uploadedFile}
 			{attachment}
 			{preview}
-			{name}
-			{type}
+			name={displayName}
 			{textContent}
 		/>
 	</Dialog.Content>
diff --git a/tools/server/webui/src/lib/types/chat.d.ts b/tools/server/webui/src/lib/types/chat.d.ts
index ee3990b04b..0eafb80cbf 100644
--- a/tools/server/webui/src/lib/types/chat.d.ts
+++ b/tools/server/webui/src/lib/types/chat.d.ts
@@ -16,7 +16,6 @@ export interface ChatAttachmentDisplayItem {
 	name: string;
 	size?: number;
 	preview?: string;
-	type: string;
 	isImage: boolean;
 	uploadedFile?: ChatUploadedFile;
 	attachment?: DatabaseMessageExtra;
@@ -29,7 +28,6 @@ export interface ChatAttachmentPreviewItem {
 	attachment?: DatabaseMessageExtra;
 	preview?: string;
 	name?: string;
-	type?: string;
 	size?: number;
 	textContent?: string;
 }
diff --git a/tools/server/webui/src/lib/utils/attachment-type.ts b/tools/server/webui/src/lib/utils/attachment-type.ts
new file mode 100644
index 0000000000..555d27af17
--- /dev/null
+++ b/tools/server/webui/src/lib/utils/attachment-type.ts
@@ -0,0 +1,126 @@
+import { AttachmentType } from '$lib/enums/attachment';
+import { FileTypeCategory } from '$lib/enums/files';
+import { getFileTypeCategory } from '$lib/utils/file-type';
+import { getFileTypeLabel } from '$lib/utils/file-preview';
+import type { DatabaseMessageExtra } from '$lib/types/database';
+
+/**
+ * Determines if an attachment or uploaded file is a text file
+ * @param uploadedFile - Optional uploaded file
+ * @param attachment - Optional database attachment
+ * @returns true if the file is a text file
+ */
+export function isTextFile(
+	attachment?: DatabaseMessageExtra,
+	uploadedFile?: ChatUploadedFile
+): boolean {
+	if (uploadedFile) {
+		return getFileTypeCategory(uploadedFile.type) === FileTypeCategory.TEXT;
+	}
+
+	if (attachment) {
+		return (
+			attachment.type === AttachmentType.TEXT || attachment.type === AttachmentType.LEGACY_CONTEXT
+		);
+	}
+
+	return false;
+}
+
+/**
+ * Determines if an attachment or uploaded file is an image
+ * @param uploadedFile - Optional uploaded file
+ * @param attachment - Optional database attachment
+ * @returns true if the file is an image
+ */
+export function isImageFile(
+	attachment?: DatabaseMessageExtra,
+	uploadedFile?: ChatUploadedFile
+): boolean {
+	if (uploadedFile) {
+		return getFileTypeCategory(uploadedFile.type) === FileTypeCategory.IMAGE;
+	}
+
+	if (attachment) {
+		return attachment.type === AttachmentType.IMAGE;
+	}
+
+	return false;
+}
+
+/**
+ * Determines if an attachment or uploaded file is a PDF
+ * @param uploadedFile - Optional uploaded file
+ * @param attachment - Optional database attachment
+ * @returns true if the file is a PDF
+ */
+export function isPdfFile(
+	attachment?: DatabaseMessageExtra,
+	uploadedFile?: ChatUploadedFile
+): boolean {
+	if (uploadedFile) {
+		return uploadedFile.type === 'application/pdf';
+	}
+
+	if (attachment) {
+		return attachment.type === AttachmentType.PDF;
+	}
+
+	return false;
+}
+
+/**
+ * Determines if an attachment or uploaded file is an audio file
+ * @param uploadedFile - Optional uploaded file
+ * @param attachment - Optional database attachment
+ * @returns true if the file is an audio file
+ */
+export function isAudioFile(
+	attachment?: DatabaseMessageExtra,
+	uploadedFile?: ChatUploadedFile
+): boolean {
+	if (uploadedFile) {
+		return getFileTypeCategory(uploadedFile.type) === FileTypeCategory.AUDIO;
+	}
+
+	if (attachment) {
+		return attachment.type === AttachmentType.AUDIO;
+	}
+
+	return false;
+}
+
+/**
+ * Gets a human-readable type label for display
+ * @param uploadedFile - Optional uploaded file
+ * @param attachment - Optional database attachment
+ * @returns A formatted type label string
+ */
+export function getAttachmentTypeLabel(
+	attachment?: DatabaseMessageExtra,
+	uploadedFile?: ChatUploadedFile
+): string {
+	if (uploadedFile) {
+		// For uploaded files, use the file type label utility
+		return getFileTypeLabel(uploadedFile.type);
+	}
+
+	if (attachment) {
+		// For attachments, convert enum to readable format
+		switch (attachment.type) {
+			case AttachmentType.IMAGE:
+				return 'image';
+			case AttachmentType.AUDIO:
+				return 'audio';
+			case AttachmentType.PDF:
+				return 'pdf';
+			case AttachmentType.TEXT:
+			case AttachmentType.LEGACY_CONTEXT:
+				return 'text';
+			default:
+				return 'unknown';
+		}
+	}
+
+	return 'unknown';
+}