feat: Attachment logic & UI improvements

2025-11-29 01:36:05 +01:00 · 2025-11-29 01:36:05 +01:00 · 648d2deebc
parent d49d97c642
commit 648d2deebc
20 changed files with 610 additions and 130 deletions
--- a/tools/server/webui/package-lock.json
+++ b/tools/server/webui/package-lock.json
@ -64,7 +64,7 @@
 				"svelte": "^5.0.0",
 				"svelte-check": "^4.0.0",
 				"tailwind-merge": "^3.3.1",
-				"tailwind-variants": "^1.0.0",
+				"tailwind-variants": "^3.2.2",
 				"tailwindcss": "^4.0.0",
 				"tw-animate-css": "^1.3.5",
 				"typescript": "^5.0.0",
@ -8324,31 +8324,23 @@
 			}
 		},
 		"node_modules/tailwind-variants": {
-			"version": "1.0.0",
-			"resolved": "https://registry.npmjs.org/tailwind-variants/-/tailwind-variants-1.0.0.tgz",
-			"integrity": "sha512-2WSbv4ulEEyuBKomOunut65D8UZwxrHoRfYnxGcQNnHqlSCp2+B7Yz2W+yrNDrxRodOXtGD/1oCcKGNBnUqMqA==",
+			"version": "3.2.2",
+			"resolved": "https://registry.npmjs.org/tailwind-variants/-/tailwind-variants-3.2.2.tgz",
+			"integrity": "sha512-Mi4kHeMTLvKlM98XPnK+7HoBPmf4gygdFmqQPaDivc3DpYS6aIY6KiG/PgThrGvii5YZJqRsPz0aPyhoFzmZgg==",
 			"dev": true,
 			"license": "MIT",
-			"dependencies": {
-				"tailwind-merge": "3.0.2"
-			},
 			"engines": {
 				"node": ">=16.x",
 				"pnpm": ">=7.x"
 			},
 			"peerDependencies": {
+				"tailwind-merge": ">=3.0.0",
 				"tailwindcss": "*"
-			}
-		},
-		"node_modules/tailwind-variants/node_modules/tailwind-merge": {
-			"version": "3.0.2",
-			"resolved": "https://registry.npmjs.org/tailwind-merge/-/tailwind-merge-3.0.2.tgz",
-			"integrity": "sha512-l7z+OYZ7mu3DTqrL88RiKrKIqO3NcpEO8V/Od04bNpvk0kiIFndGEoqfuzvj4yuhRkHKjRkII2z+KS2HfPcSxw==",
-			"dev": true,
-			"license": "MIT",
-			"funding": {
-				"type": "github",
-				"url": "https://github.com/sponsors/dcastil"
+			},
+			"peerDependenciesMeta": {
+				"tailwind-merge": {
+					"optional": true
+				}
 			}
 		},
 		"node_modules/tailwindcss": {
--- a/tools/server/webui/package.json
+++ b/tools/server/webui/package.json
@ -66,7 +66,7 @@
 		"svelte": "^5.0.0",
 		"svelte-check": "^4.0.0",
 		"tailwind-merge": "^3.3.1",
-		"tailwind-variants": "^1.0.0",
+		"tailwind-variants": "^3.2.2",
 		"tailwindcss": "^4.0.0",
 		"tw-animate-css": "^1.3.5",
 		"typescript": "^5.0.0",
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentPreview.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentPreview.svelte
@ -1,9 +1,13 @@
 <script lang="ts">
 	import { Button } from '$lib/components/ui/button';
-	import { FileText, Image, Music, FileIcon, Eye } from '@lucide/svelte';
+	import * as Alert from '$lib/components/ui/alert';
+	import { SyntaxHighlightedCode } from '$lib/components/app';
+	import { FileText, Image, Music, FileIcon, Eye, Info } from '@lucide/svelte';
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 	import { convertPDFToImage } from '$lib/utils/pdf-processing';
 	import { isTextFile, isImageFile, isPdfFile, isAudioFile } from '$lib/utils/attachment-type';
+	import { getLanguageFromFilename } from '$lib/utils/syntax-highlight-language';
+	import { modelsStore } from '$lib/stores/models.svelte';

 	interface Props {
 		// Either an uploaded file or a stored attachment
@ -13,9 +17,15 @@
 		preview?: string;
 		name?: string;
 		textContent?: string;
+		// For checking vision modality
+		activeModelId?: string;
 	}

-	let { uploadedFile, attachment, preview, name, textContent }: Props = $props();
+	let { uploadedFile, attachment, preview, name, textContent, activeModelId }: Props = $props();
+
+	let hasVisionModality = $derived(
+		activeModelId ? modelsStore.modelSupportsVision(activeModelId) : false
+	);

 	let displayName = $derived(uploadedFile?.name || attachment?.name || name || 'Unknown File');

@ -35,6 +45,8 @@
 			(attachment && 'content' in attachment ? attachment.content : textContent)
 	);

+	let language = $derived(getLanguageFromFilename(displayName));
+
 	let IconComponent = $derived(() => {
 		if (isImage) return Image;
 		if (isText || isPdf) return FileText;
@ -161,6 +173,24 @@
 				/>
 			</div>
 		{:else if isPdf && pdfViewMode === 'pages'}
+			{#if !hasVisionModality && activeModelId}
+				<Alert.Root class="mb-4">
+					<Info class="h-4 w-4" />
+					<Alert.Title>Preview only</Alert.Title>
+					<Alert.Description>
+						<span class="inline-flex">
+							The selected model does not support vision. Only the extracted
+							<!-- svelte-ignore a11y_click_events_have_key_events -->
+							<!-- svelte-ignore a11y_no_static_element_interactions -->
+							<span class="mx-1 cursor-pointer underline" onclick={() => (pdfViewMode = 'text')}>
+								text
+							</span>
+							will be sent to the model.
+						</span>
+					</Alert.Description>
+				</Alert.Root>
+			{/if}
+
 			{#if pdfImagesLoading}
 				<div class="flex items-center justify-center p-8">
 					<div class="text-center">
@ -207,11 +237,7 @@
 				</div>
 			{/if}
 		{:else if (isText || (isPdf && pdfViewMode === 'text')) && displayTextContent}
-			<div
-				class="max-h-[60vh] overflow-auto rounded-lg bg-muted p-4 font-mono text-sm break-words whitespace-pre-wrap"
-			>
-				{displayTextContent}
-			</div>
+			<SyntaxHighlightedCode code={displayTextContent} {language} maxWidth="69rem" />
 		{:else if isAudio}
 			<div class="flex items-center justify-center p-8">
 				<div class="w-full max-w-md text-center">
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsList.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsList.svelte
@ -22,6 +22,8 @@
 		imageWidth?: string;
 		// Limit display to single row with "+ X more" button
 		limitToSingleRow?: boolean;
+		// For vision modality check
+		activeModelId?: string;
 	}

 	let {
@ -35,7 +37,8 @@
 		imageClass = '',
 		imageHeight = 'h-24',
 		imageWidth = 'w-auto',
-		limitToSingleRow = false
+		limitToSingleRow = false,
+		activeModelId
 	}: Props = $props();

 	let displayItems = $derived(getAttachmentDisplayItems({ uploadedFiles, attachments }));
@ -226,6 +229,7 @@
 		name={previewItem.name}
 		size={previewItem.size}
 		textContent={previewItem.textContent}
+		{activeModelId}
 	/>
 {/if}

@ -237,4 +241,5 @@
 	{onFileRemove}
 	imageHeight="h-64"
 	{imageClass}
+	{activeModelId}
 />
--- a/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatAttachments/ChatAttachmentsViewAll.svelte
@ -16,6 +16,7 @@
 		imageHeight?: string;
 		imageWidth?: string;
 		imageClass?: string;
+		activeModelId?: string;
 	}

 	let {
@ -25,7 +26,8 @@
 		onFileRemove,
 		imageHeight = 'h-24',
 		imageWidth = 'w-auto',
-		imageClass = ''
+		imageClass = '',
+		activeModelId
 	}: Props = $props();

 	let previewDialogOpen = $state(false);
@ -112,5 +114,6 @@
 		name={previewItem.name}
 		size={previewItem.size}
 		textContent={previewItem.textContent}
+		{activeModelId}
 	/>
 {/if}
--- a/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatForm.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatForm/ChatForm.svelte
@ -333,6 +333,7 @@
 		limitToSingleRow
 		class="py-5"
 		style="scroll-padding: 1rem;"
+		activeModelId={activeModelId ?? undefined}
 	/>

 	<div
--- a/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
+++ b/tools/server/webui/src/lib/components/app/chat/ChatScreen/ChatScreen.svelte
@ -10,6 +10,7 @@
 		ServerLoadingSplash,
 		DialogConfirmation
 	} from '$lib/components/app';
+	import * as Alert from '$lib/components/ui/alert';
 	import * as AlertDialog from '$lib/components/ui/alert-dialog';
 	import {
 		AUTO_SCROLL_AT_BOTTOM_THRESHOLD,
@ -389,23 +390,21 @@
 					class="pointer-events-auto mx-auto mb-3 max-w-[48rem] px-4"
 					in:fly={{ y: 10, duration: 250 }}
 				>
-					<div class="rounded-xl border border-destructive/30 bg-destructive/10 px-4 py-3">
-						<div class="flex items-center justify-between">
-							<div class="flex items-center gap-2">
-								<AlertTriangle class="h-4 w-4 text-destructive" />
-								<span class="text-sm font-medium text-destructive">Server unavailable</span>
-								<span class="text-sm text-muted-foreground">— {serverError()}</span>
-							</div>
+					<Alert.Root variant="destructive">
+						<AlertTriangle class="h-4 w-4" />
+						<Alert.Title class="flex items-center justify-between">
+							<span>Server unavailable</span>
 							<button
 								onclick={() => serverStore.fetch()}
 								disabled={isServerLoading}
-								class="flex items-center gap-1.5 rounded-lg bg-destructive/20 px-3 py-1.5 text-xs font-medium text-destructive hover:bg-destructive/30 disabled:opacity-50"
+								class="flex items-center gap-1.5 rounded-lg bg-destructive/20 px-2 py-1 text-xs font-medium hover:bg-destructive/30 disabled:opacity-50"
 							>
 								<RefreshCw class="h-3 w-3 {isServerLoading ? 'animate-spin' : ''}" />
 								{isServerLoading ? 'Retrying...' : 'Retry'}
 							</button>
-						</div>
-					</div>
+						</Alert.Title>
+						<Alert.Description>{serverError()}</Alert.Description>
+					</Alert.Root>
 				</div>
 			{/if}

@ -449,23 +448,21 @@

 			{#if hasPropsError}
 				<div class="mb-4" in:fly={{ y: 10, duration: 250 }}>
-					<div class="rounded-xl border border-destructive/30 bg-destructive/10 px-4 py-3">
-						<div class="flex items-center justify-between">
-							<div class="flex items-center gap-2">
-								<AlertTriangle class="h-4 w-4 text-destructive" />
-								<span class="text-sm font-medium text-destructive">Server unavailable</span>
-								<span class="text-sm text-muted-foreground">— {serverError()}</span>
-							</div>
+					<Alert.Root variant="destructive">
+						<AlertTriangle class="h-4 w-4" />
+						<Alert.Title class="flex items-center justify-between">
+							<span>Server unavailable</span>
 							<button
 								onclick={() => serverStore.fetch()}
 								disabled={isServerLoading}
-								class="flex items-center gap-1.5 rounded-lg bg-destructive/20 px-3 py-1.5 text-xs font-medium text-destructive hover:bg-destructive/30 disabled:opacity-50"
+								class="flex items-center gap-1.5 rounded-lg bg-destructive/20 px-2 py-1 text-xs font-medium hover:bg-destructive/30 disabled:opacity-50"
 							>
 								<RefreshCw class="h-3 w-3 {isServerLoading ? 'animate-spin' : ''}" />
 								{isServerLoading ? 'Retrying...' : 'Retry'}
 							</button>
-						</div>
-					</div>
+						</Alert.Title>
+						<Alert.Description>{serverError()}</Alert.Description>
+					</Alert.Root>
 				</div>
 			{/if}

--- a/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentPreview.svelte
+++ b/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentPreview.svelte
@ -3,7 +3,6 @@
 	import type { DatabaseMessageExtra } from '$lib/types/database';
 	import { ChatAttachmentPreview } from '$lib/components/app';
 	import { formatFileSize } from '$lib/utils/formatters';
-	import { getAttachmentTypeLabel } from '$lib/utils/attachment-type';

 	interface Props {
 		open: boolean;
@ -16,6 +15,8 @@
 		name?: string;
 		size?: number;
 		textContent?: string;
+		// For vision modality check
+		activeModelId?: string;
 	}

 	let {
@ -26,7 +27,8 @@
 		preview,
 		name,
 		size,
-		textContent
+		textContent,
+		activeModelId
 	}: Props = $props();

 	let chatAttachmentPreviewRef: ChatAttachmentPreview | undefined = $state();
@ -35,8 +37,6 @@

 	let displaySize = $derived(uploadedFile?.size || size);

-	let typeLabel = $derived(getAttachmentTypeLabel(uploadedFile, attachment));
-
 	$effect(() => {
 		if (open && chatAttachmentPreviewRef) {
 			chatAttachmentPreviewRef.reset();
@ -49,9 +49,8 @@
 		<Dialog.Header>
 			<Dialog.Title class="pr-8">{displayName}</Dialog.Title>
 			<Dialog.Description>
-				{typeLabel}
 				{#if displaySize}
-					• {formatFileSize(displaySize)}
+					{formatFileSize(displaySize)}
 				{/if}
 			</Dialog.Description>
 		</Dialog.Header>
@ -63,6 +62,7 @@
 			{preview}
 			name={displayName}
 			{textContent}
+			{activeModelId}
 		/>
 	</Dialog.Content>
 </Dialog.Root>
--- a/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentsViewAll.svelte
+++ b/tools/server/webui/src/lib/components/app/dialogs/DialogChatAttachmentsViewAll.svelte
@ -11,6 +11,7 @@
 		imageHeight?: string;
 		imageWidth?: string;
 		imageClass?: string;
+		activeModelId?: string;
 	}

 	let {
@ -21,7 +22,8 @@
 		onFileRemove,
 		imageHeight = 'h-24',
 		imageWidth = 'w-auto',
-		imageClass = ''
+		imageClass = '',
+		activeModelId
 	}: Props = $props();

 	let totalCount = $derived(uploadedFiles.length + attachments.length);
@ -45,6 +47,7 @@
 				{imageHeight}
 				{imageWidth}
 				{imageClass}
+				{activeModelId}
 			/>
 		</Dialog.Content>
 	</Dialog.Portal>
--- a/tools/server/webui/src/lib/components/app/index.ts
+++ b/tools/server/webui/src/lib/components/app/index.ts
@ -62,6 +62,7 @@ export { default as CopyToClipboardIcon } from './misc/CopyToClipboardIcon.svelt
 export { default as KeyboardShortcutInfo } from './misc/KeyboardShortcutInfo.svelte';
 export { default as MarkdownContent } from './misc/MarkdownContent.svelte';
 export { default as RemoveButton } from './misc/RemoveButton.svelte';
+export { default as SyntaxHighlightedCode } from './misc/SyntaxHighlightedCode.svelte';
 export { default as ModelsSelector } from './models/ModelsSelector.svelte';

 // Server
--- a/tools/server/webui/src/lib/components/app/misc/SyntaxHighlightedCode.svelte
+++ b/tools/server/webui/src/lib/components/app/misc/SyntaxHighlightedCode.svelte
@ -0,0 +1,96 @@
+<script lang="ts">
+	import hljs from 'highlight.js';
+	import { browser } from '$app/environment';
+	import { mode } from 'mode-watcher';
+
+	import githubDarkCss from 'highlight.js/styles/github-dark.css?inline';
+	import githubLightCss from 'highlight.js/styles/github.css?inline';
+
+	interface Props {
+		code: string;
+		language?: string;
+		class?: string;
+		maxHeight?: string;
+		maxWidth?: string;
+	}
+
+	let {
+		code,
+		language = 'text',
+		class: className = '',
+		maxHeight = '60vh',
+		maxWidth = ''
+	}: Props = $props();
+
+	let highlightedHtml = $state('');
+
+	function loadHighlightTheme(isDark: boolean) {
+		if (!browser) return;
+
+		const existingThemes = document.querySelectorAll('style[data-highlight-theme-preview]');
+		existingThemes.forEach((style) => style.remove());
+
+		const style = document.createElement('style');
+		style.setAttribute('data-highlight-theme-preview', 'true');
+		style.textContent = isDark ? githubDarkCss : githubLightCss;
+
+		document.head.appendChild(style);
+	}
+
+	$effect(() => {
+		const currentMode = mode.current;
+		const isDark = currentMode === 'dark';
+
+		loadHighlightTheme(isDark);
+	});
+
+	$effect(() => {
+		if (!code) {
+			highlightedHtml = '';
+			return;
+		}
+
+		try {
+			// Check if the language is supported
+			const lang = language.toLowerCase();
+			const isSupported = hljs.getLanguage(lang);
+
+			if (isSupported) {
+				const result = hljs.highlight(code, { language: lang });
+				highlightedHtml = result.value;
+			} else {
+				// Try auto-detection or fallback to plain text
+				const result = hljs.highlightAuto(code);
+				highlightedHtml = result.value;
+			}
+		} catch {
+			// Fallback to escaped plain text
+			highlightedHtml = code.replace(/&/g, '&amp;').replace(/</g, '&lt;').replace(/>/g, '&gt;');
+		}
+	});
+</script>
+
+<div
+	class="code-preview-wrapper overflow-auto rounded-lg border border-border bg-muted {className}"
+	style="max-height: {maxHeight};"
+>
+	<pre class="m-0 overflow-x-auto p-4 max-w-[{maxWidth}]"><code class="hljs text-sm leading-relaxed"
+			>{@html highlightedHtml}</code
+		></pre>
+</div>
+
+<style>
+	.code-preview-wrapper {
+		font-family:
+			ui-monospace, SFMono-Regular, 'SF Mono', Monaco, 'Cascadia Code', 'Roboto Mono', Consolas,
+			'Liberation Mono', Menlo, monospace;
+	}
+
+	.code-preview-wrapper pre {
+		background: transparent;
+	}
+
+	.code-preview-wrapper code {
+		background: transparent;
+	}
+</style>
--- a/tools/server/webui/src/lib/components/ui/alert/alert-description.svelte
+++ b/tools/server/webui/src/lib/components/ui/alert/alert-description.svelte
@ -0,0 +1,23 @@
+<script lang="ts">
+	import type { HTMLAttributes } from 'svelte/elements';
+	import { cn, type WithElementRef } from '$lib/components/ui/utils.js';
+
+	let {
+		ref = $bindable(null),
+		class: className,
+		children,
+		...restProps
+	}: WithElementRef<HTMLAttributes<HTMLDivElement>> = $props();
+</script>
+
+<div
+	bind:this={ref}
+	data-slot="alert-description"
+	class={cn(
+		'col-start-2 grid justify-items-start gap-1 text-sm text-muted-foreground [&_p]:leading-relaxed',
+		className
+	)}
+	{...restProps}
+>
+	{@render children?.()}
+</div>
--- a/tools/server/webui/src/lib/components/ui/alert/alert-title.svelte
+++ b/tools/server/webui/src/lib/components/ui/alert/alert-title.svelte
@ -0,0 +1,20 @@
+<script lang="ts">
+	import type { HTMLAttributes } from 'svelte/elements';
+	import { cn, type WithElementRef } from '$lib/components/ui/utils.js';
+
+	let {
+		ref = $bindable(null),
+		class: className,
+		children,
+		...restProps
+	}: WithElementRef<HTMLAttributes<HTMLDivElement>> = $props();
+</script>
+
+<div
+	bind:this={ref}
+	data-slot="alert-title"
+	class={cn('col-start-2 line-clamp-1 min-h-4 font-medium tracking-tight', className)}
+	{...restProps}
+>
+	{@render children?.()}
+</div>
--- a/tools/server/webui/src/lib/components/ui/alert/alert.svelte
+++ b/tools/server/webui/src/lib/components/ui/alert/alert.svelte
@ -0,0 +1,44 @@
+<script lang="ts" module>
+	import { type VariantProps, tv } from 'tailwind-variants';
+
+	export const alertVariants = tv({
+		base: 'relative grid w-full grid-cols-[0_1fr] items-start gap-y-0.5 rounded-lg border px-4 py-3 text-sm has-[>svg]:grid-cols-[calc(var(--spacing)*4)_1fr] has-[>svg]:gap-x-3 [&>svg]:size-4 [&>svg]:translate-y-0.5 [&>svg]:text-current',
+		variants: {
+			variant: {
+				default: 'bg-card text-card-foreground',
+				destructive:
+					'text-destructive bg-card *:data-[slot=alert-description]:text-destructive/90 [&>svg]:text-current'
+			}
+		},
+		defaultVariants: {
+			variant: 'default'
+		}
+	});
+
+	export type AlertVariant = VariantProps<typeof alertVariants>['variant'];
+</script>
+
+<script lang="ts">
+	import type { HTMLAttributes } from 'svelte/elements';
+	import { cn, type WithElementRef } from '$lib/components/ui/utils.js';
+
+	let {
+		ref = $bindable(null),
+		class: className,
+		variant = 'default',
+		children,
+		...restProps
+	}: WithElementRef<HTMLAttributes<HTMLDivElement>> & {
+		variant?: AlertVariant;
+	} = $props();
+</script>
+
+<div
+	bind:this={ref}
+	data-slot="alert"
+	class={cn(alertVariants({ variant }), className)}
+	{...restProps}
+	role="alert"
+>
+	{@render children?.()}
+</div>
--- a/tools/server/webui/src/lib/components/ui/alert/index.ts
+++ b/tools/server/webui/src/lib/components/ui/alert/index.ts
@ -0,0 +1,14 @@
+import Root from './alert.svelte';
+import Description from './alert-description.svelte';
+import Title from './alert-title.svelte';
+export { alertVariants, type AlertVariant } from './alert.svelte';
+
+export {
+	Root,
+	Description,
+	Title,
+	//
+	Root as Alert,
+	Description as AlertDescription,
+	Title as AlertTitle
+};
--- a/tools/server/webui/src/lib/utils/attachment-display.ts
+++ b/tools/server/webui/src/lib/utils/attachment-display.ts
@ -2,13 +2,26 @@ import { FileTypeCategory } from '$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';
+import { getFileTypeCategory, getFileTypeCategoryByExtension } from '$lib/utils/file-type';

 export interface AttachmentDisplayItemsOptions {
 	uploadedFiles?: ChatUploadedFile[];
 	attachments?: DatabaseMessageExtra[];
 }

+/**
+ * Gets the file type category from an uploaded file, checking both MIME type and extension
+ */
+function getUploadedFileCategory(file: ChatUploadedFile): FileTypeCategory | null {
+	const categoryByMime = getFileTypeCategory(file.type);
+
+	if (categoryByMime) {
+		return categoryByMime;
+	}
+
+	return getFileTypeCategoryByExtension(file.name);
+}
+
 /**
 * Creates a unified list of display items from uploaded files and stored attachments.
 * Items are returned in reverse order (newest first).
@ -26,7 +39,7 @@ export function getAttachmentDisplayItems(
 			name: file.name,
 			size: file.size,
 			preview: file.preview,
-			isImage: getFileTypeCategory(file.type) === FileTypeCategory.IMAGE,
+			isImage: getUploadedFileCategory(file) === FileTypeCategory.IMAGE,
 			uploadedFile: file,
 			textContent: file.textContent
 		});
--- a/tools/server/webui/src/lib/utils/attachment-type.ts
+++ b/tools/server/webui/src/lib/utils/attachment-type.ts
@ -1,8 +1,24 @@
 import { AttachmentType, FileTypeCategory } from '$lib/enums';
-import { getFileTypeCategory } from '$lib/utils/file-type';
-import { getFileTypeLabel } from '$lib/utils/file-preview';
+import { getFileTypeCategory, getFileTypeCategoryByExtension } from '$lib/utils/file-type';
 import type { DatabaseMessageExtra } from '$lib/types/database';

+/**
+ * Gets the file type category from an uploaded file, checking both MIME type and extension
+ * @param uploadedFile - The uploaded file to check
+ * @returns The file type category or null if not recognized
+ */
+function getUploadedFileCategory(uploadedFile: ChatUploadedFile): FileTypeCategory | null {
+	// First try MIME type
+	const categoryByMime = getFileTypeCategory(uploadedFile.type);
+
+	if (categoryByMime) {
+		return categoryByMime;
+	}
+
+	// Fallback to extension (browsers don't always provide correct MIME types)
+	return getFileTypeCategoryByExtension(uploadedFile.name);
+}
+
 /**
 * Determines if an attachment or uploaded file is a text file
 * @param uploadedFile - Optional uploaded file
@ -14,7 +30,7 @@ export function isTextFile(
 	uploadedFile?: ChatUploadedFile
 ): boolean {
 	if (uploadedFile) {
-		return getFileTypeCategory(uploadedFile.type) === FileTypeCategory.TEXT;
+		return getUploadedFileCategory(uploadedFile) === FileTypeCategory.TEXT;
 	}

 	if (attachment) {
@ -37,7 +53,7 @@ export function isImageFile(
 	uploadedFile?: ChatUploadedFile
 ): boolean {
 	if (uploadedFile) {
-		return getFileTypeCategory(uploadedFile.type) === FileTypeCategory.IMAGE;
+		return getUploadedFileCategory(uploadedFile) === FileTypeCategory.IMAGE;
 	}

 	if (attachment) {
@ -58,7 +74,7 @@ export function isPdfFile(
 	uploadedFile?: ChatUploadedFile
 ): boolean {
 	if (uploadedFile) {
-		return uploadedFile.type === 'application/pdf';
+		return getUploadedFileCategory(uploadedFile) === FileTypeCategory.PDF;
 	}

 	if (attachment) {
@ -79,7 +95,7 @@ export function isAudioFile(
 	uploadedFile?: ChatUploadedFile
 ): boolean {
 	if (uploadedFile) {
-		return getFileTypeCategory(uploadedFile.type) === FileTypeCategory.AUDIO;
+		return getUploadedFileCategory(uploadedFile) === FileTypeCategory.AUDIO;
 	}

 	if (attachment) {
@ -88,38 +104,3 @@ export function isAudioFile(

 	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';
-}
--- a/tools/server/webui/src/lib/utils/file-type.ts
+++ b/tools/server/webui/src/lib/utils/file-type.ts
@ -4,42 +4,151 @@ import {
 	PDF_FILE_TYPES,
 	TEXT_FILE_TYPES
 } from '$lib/constants/supported-file-types';
-import { FileTypeCategory } from '$lib/enums';
+import {
+	FileExtensionAudio,
+	FileExtensionImage,
+	FileExtensionPdf,
+	FileExtensionText,
+	FileTypeCategory,
+	MimeTypeApplication,
+	MimeTypeAudio,
+	MimeTypeImage,
+	MimeTypeText
+} from '$lib/enums';

 export function getFileTypeCategory(mimeType: string): FileTypeCategory | null {
-	if (
-		Object.values(IMAGE_FILE_TYPES).some((type) =>
-			(type.mimeTypes as readonly string[]).includes(mimeType)
-		)
-	) {
-		return FileTypeCategory.IMAGE;
-	}
+	switch (mimeType) {
+		// Images
+		case MimeTypeImage.JPEG:
+		case MimeTypeImage.PNG:
+		case MimeTypeImage.GIF:
+		case MimeTypeImage.WEBP:
+		case MimeTypeImage.SVG:
+			return FileTypeCategory.IMAGE;

-	if (
-		Object.values(AUDIO_FILE_TYPES).some((type) =>
-			(type.mimeTypes as readonly string[]).includes(mimeType)
-		)
-	) {
-		return FileTypeCategory.AUDIO;
-	}
+		// Audio
+		case MimeTypeAudio.MP3_MPEG:
+		case MimeTypeAudio.MP3:
+		case MimeTypeAudio.MP4:
+		case MimeTypeAudio.WAV:
+		case MimeTypeAudio.WEBM:
+		case MimeTypeAudio.WEBM_OPUS:
+			return FileTypeCategory.AUDIO;

-	if (
-		Object.values(PDF_FILE_TYPES).some((type) =>
-			(type.mimeTypes as readonly string[]).includes(mimeType)
-		)
-	) {
-		return FileTypeCategory.PDF;
-	}
+		// PDF
+		case MimeTypeApplication.PDF:
+			return FileTypeCategory.PDF;

-	if (
-		Object.values(TEXT_FILE_TYPES).some((type) =>
-			(type.mimeTypes as readonly string[]).includes(mimeType)
-		)
-	) {
-		return FileTypeCategory.TEXT;
-	}
+		// Text
+		case MimeTypeText.PLAIN:
+		case MimeTypeText.MARKDOWN:
+		case MimeTypeText.ASCIIDOC:
+		case MimeTypeText.JAVASCRIPT:
+		case MimeTypeText.JAVASCRIPT_APP:
+		case MimeTypeText.TYPESCRIPT:
+		case MimeTypeText.JSX:
+		case MimeTypeText.TSX:
+		case MimeTypeText.CSS:
+		case MimeTypeText.HTML:
+		case MimeTypeText.JSON:
+		case MimeTypeText.XML_TEXT:
+		case MimeTypeText.XML_APP:
+		case MimeTypeText.YAML_TEXT:
+		case MimeTypeText.YAML_APP:
+		case MimeTypeText.CSV:
+		case MimeTypeText.PYTHON:
+		case MimeTypeText.JAVA:
+		case MimeTypeText.CPP_SRC:
+		case MimeTypeText.C_SRC:
+		case MimeTypeText.C_HDR:
+		case MimeTypeText.PHP:
+		case MimeTypeText.RUBY:
+		case MimeTypeText.GO:
+		case MimeTypeText.RUST:
+		case MimeTypeText.SHELL:
+		case MimeTypeText.BAT:
+		case MimeTypeText.SQL:
+		case MimeTypeText.R:
+		case MimeTypeText.SCALA:
+		case MimeTypeText.KOTLIN:
+		case MimeTypeText.SWIFT:
+		case MimeTypeText.DART:
+		case MimeTypeText.VUE:
+		case MimeTypeText.SVELTE:
+		case MimeTypeText.LATEX:
+		case MimeTypeText.BIBTEX:
+			return FileTypeCategory.TEXT;

-	return null;
+		default:
+			return null;
+	}
+}
+
+export function getFileTypeCategoryByExtension(filename: string): FileTypeCategory | null {
+	const extension = filename.toLowerCase().substring(filename.lastIndexOf('.'));
+
+	switch (extension) {
+		// Images
+		case FileExtensionImage.JPG:
+		case FileExtensionImage.JPEG:
+		case FileExtensionImage.PNG:
+		case FileExtensionImage.GIF:
+		case FileExtensionImage.WEBP:
+		case FileExtensionImage.SVG:
+			return FileTypeCategory.IMAGE;
+
+		// Audio
+		case FileExtensionAudio.MP3:
+		case FileExtensionAudio.WAV:
+			return FileTypeCategory.AUDIO;
+
+		// PDF
+		case FileExtensionPdf.PDF:
+			return FileTypeCategory.PDF;
+
+		// Text
+		case FileExtensionText.TXT:
+		case FileExtensionText.MD:
+		case FileExtensionText.ADOC:
+		case FileExtensionText.JS:
+		case FileExtensionText.TS:
+		case FileExtensionText.JSX:
+		case FileExtensionText.TSX:
+		case FileExtensionText.CSS:
+		case FileExtensionText.HTML:
+		case FileExtensionText.HTM:
+		case FileExtensionText.JSON:
+		case FileExtensionText.XML:
+		case FileExtensionText.YAML:
+		case FileExtensionText.YML:
+		case FileExtensionText.CSV:
+		case FileExtensionText.LOG:
+		case FileExtensionText.PY:
+		case FileExtensionText.JAVA:
+		case FileExtensionText.CPP:
+		case FileExtensionText.C:
+		case FileExtensionText.H:
+		case FileExtensionText.PHP:
+		case FileExtensionText.RB:
+		case FileExtensionText.GO:
+		case FileExtensionText.RS:
+		case FileExtensionText.SH:
+		case FileExtensionText.BAT:
+		case FileExtensionText.SQL:
+		case FileExtensionText.R:
+		case FileExtensionText.SCALA:
+		case FileExtensionText.KT:
+		case FileExtensionText.SWIFT:
+		case FileExtensionText.DART:
+		case FileExtensionText.VUE:
+		case FileExtensionText.SVELTE:
+		case FileExtensionText.TEX:
+		case FileExtensionText.BIB:
+			return FileTypeCategory.TEXT;
+
+		default:
+			return null;
+	}
 }

 export function getFileTypeByExtension(filename: string): string | null {
--- a/tools/server/webui/src/lib/utils/process-uploaded-files.ts
+++ b/tools/server/webui/src/lib/utils/process-uploaded-files.ts
@ -6,6 +6,7 @@ import { getFileTypeCategory } from '$lib/utils/file-type';
 import { modelsStore } from '$lib/stores/models.svelte';
 import { settingsStore } from '$lib/stores/settings.svelte';
 import { toast } from 'svelte-sonner';
+import { convertPDFToText } from '$lib/utils/pdf-processing';

 /**
 * Read a file as a data URL (base64 encoded)
@ -95,8 +96,14 @@ export async function processFilesToChatUploaded(
 					results.push(base);
 				}
 			} else if (getFileTypeCategory(file.type) === FileTypeCategory.PDF) {
-				// PDFs handled later when building extras; keep metadata only
-				results.push(base);
+				// Extract text content from PDF for preview
+				try {
+					const textContent = await convertPDFToText(file);
+					results.push({ ...base, textContent });
+				} catch (err) {
+					console.warn('Failed to extract text from PDF, adding without content:', err);
+					results.push(base);
+				}

 				// Show suggestion toast if vision model is available but PDF as image is disabled
 				const hasVisionSupport = activeModelId
--- a/tools/server/webui/src/lib/utils/syntax-highlight-language.ts
+++ b/tools/server/webui/src/lib/utils/syntax-highlight-language.ts
@ -0,0 +1,145 @@
+/**
+ * Maps file extensions to highlight.js language identifiers
+ */
+export function getLanguageFromFilename(filename: string): string {
+	const extension = filename.toLowerCase().substring(filename.lastIndexOf('.'));
+
+	switch (extension) {
+		// JavaScript / TypeScript
+		case '.js':
+		case '.mjs':
+		case '.cjs':
+			return 'javascript';
+		case '.ts':
+		case '.mts':
+		case '.cts':
+			return 'typescript';
+		case '.jsx':
+			return 'javascript';
+		case '.tsx':
+			return 'typescript';
+
+		// Web
+		case '.html':
+		case '.htm':
+			return 'html';
+		case '.css':
+			return 'css';
+		case '.scss':
+			return 'scss';
+		case '.less':
+			return 'less';
+		case '.vue':
+			return 'html';
+		case '.svelte':
+			return 'html';
+
+		// Data formats
+		case '.json':
+			return 'json';
+		case '.xml':
+			return 'xml';
+		case '.yaml':
+		case '.yml':
+			return 'yaml';
+		case '.toml':
+			return 'ini';
+		case '.csv':
+			return 'plaintext';
+
+		// Programming languages
+		case '.py':
+			return 'python';
+		case '.java':
+			return 'java';
+		case '.kt':
+		case '.kts':
+			return 'kotlin';
+		case '.scala':
+			return 'scala';
+		case '.cpp':
+		case '.cc':
+		case '.cxx':
+		case '.c++':
+			return 'cpp';
+		case '.c':
+			return 'c';
+		case '.h':
+		case '.hpp':
+			return 'cpp';
+		case '.cs':
+			return 'csharp';
+		case '.go':
+			return 'go';
+		case '.rs':
+			return 'rust';
+		case '.rb':
+			return 'ruby';
+		case '.php':
+			return 'php';
+		case '.swift':
+			return 'swift';
+		case '.dart':
+			return 'dart';
+		case '.r':
+			return 'r';
+		case '.lua':
+			return 'lua';
+		case '.pl':
+		case '.pm':
+			return 'perl';
+
+		// Shell
+		case '.sh':
+		case '.bash':
+		case '.zsh':
+			return 'bash';
+		case '.bat':
+		case '.cmd':
+			return 'dos';
+		case '.ps1':
+			return 'powershell';
+
+		// Database
+		case '.sql':
+			return 'sql';
+
+		// Markup / Documentation
+		case '.md':
+		case '.markdown':
+			return 'markdown';
+		case '.tex':
+		case '.latex':
+			return 'latex';
+		case '.adoc':
+		case '.asciidoc':
+			return 'asciidoc';
+
+		// Config
+		case '.ini':
+		case '.cfg':
+		case '.conf':
+			return 'ini';
+		case '.dockerfile':
+			return 'dockerfile';
+		case '.nginx':
+			return 'nginx';
+
+		// Other
+		case '.graphql':
+		case '.gql':
+			return 'graphql';
+		case '.proto':
+			return 'protobuf';
+		case '.diff':
+		case '.patch':
+			return 'diff';
+		case '.log':
+			return 'plaintext';
+		case '.txt':
+			return 'plaintext';
+
+		default:
+			return 'plaintext';
+	}
+}