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 cecdc784c9..73ef7852e1 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
@@ -145,7 +145,9 @@
 
 		<div class="flex flex-col gap-0.5">
 			<span
-				class="max-w-24 truncate text-sm font-medium text-foreground group-hover:pr-6 md:max-w-32"
+				class="max-w-24 truncate text-sm font-medium text-foreground {readonly
+					? ''
+					: 'group-hover:pr-6'} md:max-w-32"
 			>
 				{name}
 			</span>
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 46fc2d4313..7e29df60b0 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
@@ -2,10 +2,8 @@
 	import { ChatAttachmentThumbnailImage, ChatAttachmentThumbnailFile } from '$lib/components/app';
 	import { Button } from '$lib/components/ui/button';
 	import { ChevronLeft, ChevronRight } from '@lucide/svelte';
-	import { getFileTypeCategory } from '$lib/utils/file-type';
-	import { FileTypeCategory } from '$lib/enums';
-	import { isImageFile } from '$lib/utils/attachment-type';
 	import { DialogChatAttachmentPreview, DialogChatAttachmentsViewAll } from '$lib/components/app';
+	import { getAttachmentDisplayItems } from '$lib/utils/attachment-display';
 	import type { ChatAttachmentDisplayItem, ChatAttachmentPreviewItem } from '$lib/types/chat';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 
@@ -40,7 +38,7 @@
 		limitToSingleRow = false
 	}: Props = $props();
 
-	let displayItems = $derived(getDisplayItems());
+	let displayItems = $derived(getAttachmentDisplayItems({ uploadedFiles, attachments }));
 
 	let canScrollLeft = $state(false);
 	let canScrollRight = $state(false);
@@ -51,40 +49,6 @@
 	let showViewAll = $derived(limitToSingleRow && displayItems.length > 0 && isScrollable);
 	let viewAllDialogOpen = $state(false);
 
-	function getDisplayItems(): ChatAttachmentDisplayItem[] {
-		const items: ChatAttachmentDisplayItem[] = [];
-
-		// Add uploaded files (ChatForm)
-		for (const file of uploadedFiles) {
-			items.push({
-				id: file.id,
-				name: file.name,
-				size: file.size,
-				preview: file.preview,
-				isImage: getFileTypeCategory(file.type) === FileTypeCategory.IMAGE,
-				uploadedFile: file,
-				textContent: file.textContent
-			});
-		}
-
-		// Add stored attachments (ChatMessage)
-		for (const [index, attachment] of attachments.entries()) {
-			const isImage = isImageFile(attachment);
-
-			items.push({
-				id: `attachment-${index}`,
-				name: attachment.name,
-				preview: isImage && 'base64Url' in attachment ? attachment.base64Url : undefined,
-				isImage,
-				attachment,
-				attachmentIndex: index,
-				textContent: 'content' in attachment ? attachment.content : undefined
-			});
-		}
-
-		return items.reverse();
-	}
-
 	function openPreview(item: ChatAttachmentDisplayItem, event?: MouseEvent) {
 		event?.stopPropagation();
 		event?.preventDefault();
@@ -218,7 +182,7 @@
 				</div>
 			{/if}
 		{:else}
-			<div class="flex flex-wrap justify-end gap-3">
+			<div class="flex flex-wrap items-start justify-end gap-3">
 				{#each displayItems as item (item.id)}
 					{#if item.isImage && item.preview}
 						<ChatAttachmentThumbnailImage
diff --git a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
index 427ff32a7b..2898090041 100644
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
@@ -4,10 +4,8 @@
 		ChatAttachmentThumbnailFile,
 		DialogChatAttachmentPreview
 	} from '$lib/components/app';
-	import { FileTypeCategory } from '$lib/enums';
-	import { getFileTypeCategory } from '$lib/utils/file-type';
-	import { isImageFile } from '$lib/utils/attachment-type';
-	import type { ChatAttachmentDisplayItem, ChatAttachmentPreviewItem } from '$lib/types/chat';
+	import { getAttachmentDisplayItems } from '$lib/utils/attachment-display';
+	import type { ChatAttachmentPreviewItem } from '$lib/types/chat';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 
 	interface Props {
@@ -33,42 +31,10 @@
 	let previewDialogOpen = $state(false);
 	let previewItem = $state<ChatAttachmentPreviewItem | null>(null);
 
-	let displayItems = $derived(getDisplayItems());
+	let displayItems = $derived(getAttachmentDisplayItems({ uploadedFiles, attachments }));
 	let imageItems = $derived(displayItems.filter((item) => item.isImage));
 	let fileItems = $derived(displayItems.filter((item) => !item.isImage));
 
-	function getDisplayItems(): ChatAttachmentDisplayItem[] {
-		const items: ChatAttachmentDisplayItem[] = [];
-
-		for (const file of uploadedFiles) {
-			items.push({
-				id: file.id,
-				name: file.name,
-				size: file.size,
-				preview: file.preview,
-				isImage: getFileTypeCategory(file.type) === FileTypeCategory.IMAGE,
-				uploadedFile: file,
-				textContent: file.textContent
-			});
-		}
-
-		for (const [index, attachment] of attachments.entries()) {
-			const isImage = isImageFile(attachment);
-
-			items.push({
-				id: `attachment-${index}`,
-				name: attachment.name,
-				preview: isImage && 'base64Url' in attachment ? attachment.base64Url : undefined,
-				isImage,
-				attachment,
-				attachmentIndex: index,
-				textContent: 'content' in attachment ? attachment.content : undefined
-			});
-		}
-
-		return items.reverse();
-	}
-
 	function openPreview(item: (typeof displayItems)[0], event?: Event) {
 		if (event) {
 			event.preventDefault();
diff --git a/tools/server/webui/src/lib/utils/attachment-display.ts b/tools/server/webui/src/lib/utils/attachment-display.ts
new file mode 100644
index 0000000000..1fc166a881
--- /dev/null
+++ b/tools/server/webui/src/lib/utils/attachment-display.ts
@@ -0,0 +1,51 @@
+import { FileTypeCategory } from '$lib/enums';
+import type { ChatAttachmentDisplayItem } from '$lib/types/chat';
+import type { DatabaseMessageExtra } from '$lib/types/database';
+import { isImageFile } from '$lib/utils/attachment-type';
+import { getFileTypeCategory } from '$lib/utils/file-type';
+
+export interface AttachmentDisplayItemsOptions {
+	uploadedFiles?: ChatUploadedFile[];
+	attachments?: DatabaseMessageExtra[];
+}
+
+/**
+ * Creates a unified list of display items from uploaded files and stored attachments.
+ * Items are returned in reverse order (newest first).
+ */
+export function getAttachmentDisplayItems(
+	options: AttachmentDisplayItemsOptions
+): ChatAttachmentDisplayItem[] {
+	const { uploadedFiles = [], attachments = [] } = options;
+	const items: ChatAttachmentDisplayItem[] = [];
+
+	// Add uploaded files (ChatForm)
+	for (const file of uploadedFiles) {
+		items.push({
+			id: file.id,
+			name: file.name,
+			size: file.size,
+			preview: file.preview,
+			isImage: getFileTypeCategory(file.type) === FileTypeCategory.IMAGE,
+			uploadedFile: file,
+			textContent: file.textContent
+		});
+	}
+
+	// Add stored attachments (ChatMessage)
+	for (const [index, attachment] of attachments.entries()) {
+		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();
+}