diff --git a/frontend/src/lib/components/admin/ImageUpload.svelte b/frontend/src/lib/components/admin/ImageUpload.svelte
index c6cf080..8fab99f 100644
--- a/frontend/src/lib/components/admin/ImageUpload.svelte
+++ b/frontend/src/lib/components/admin/ImageUpload.svelte
@@ -1,6 +1,7 @@
 <script lang="ts">
 	import { Button } from '$lib/components/ui/button';
 	import * as Card from '$lib/components/ui/card';
+	import { Input } from '$lib/components/ui/input';
 	import FileDropZone from '$lib/components/ui/file-drop-zone.svelte';
 	import { authStore } from '$lib/stores/auth.svelte';
 	import * as AlertDialog from '$lib/components/ui/alert-dialog';
@@ -8,15 +9,43 @@
 	// =============== Image Upload ===============
 	let uploading = $state(false);
 	let uploadFiles = $state<File[]>([]);
+	let filePreviews = $state<{ file: File; preview: string }[]>([]);
 	let uploadProgress = $state(0);
+	let uploadStatus = $state<Record<string, string>>({});
 	let uploadResults = $state<{ name: string; url?: string; error?: string }[]>([]);
 
 	function handleFilesDropped(files: File[]) {
 		uploadFiles = files;
+		generatePreviews(files);
 	}
 
-	/** Helper: turn any File into a JPEG-encoded Blob. */
-	function toJpegBlob(file: File): Promise<Blob> {
+	/** Generate scaled previews for each file */
+	function generatePreviews(files: File[]) {
+		filePreviews = [];
+		files.forEach((file) => {
+			const reader = new FileReader();
+			reader.onload = (e) => {
+				const img = new Image();
+				img.onload = () => {
+					const canvas = document.createElement('canvas');
+					const scale = 150 / Math.max(img.width, img.height);
+					canvas.width = img.width * scale;
+					canvas.height = img.height * scale;
+					const ctx = canvas.getContext('2d');
+					if (ctx) {
+						ctx.drawImage(img, 0, 0, canvas.width, canvas.height);
+						const preview = canvas.toDataURL('image/jpeg', 0.8);
+						filePreviews = [...filePreviews, { file, preview }];
+					}
+				};
+				img.src = e.target?.result as string;
+			};
+			reader.readAsDataURL(file);
+		});
+	}
+
+	/** Convert image to AVIF at 0.55 quality for full-size */
+	function toAvifBlob(file: File): Promise<Blob> {
 		return new Promise((resolve, reject) => {
 			const img = new Image();
 			img.onload = () => {
@@ -29,10 +58,12 @@
 				canvas.toBlob(
 					(blob) => {
 						if (!blob) return reject(new Error('Canvas toBlob failed'));
-						resolve(blob);
+						// Ensure blob has correct MIME type
+						const typedBlob = new Blob([blob], { type: 'image/avif' });
+						resolve(typedBlob);
 					},
-					'image/jpeg',
-					0.92
+					'image/avif',
+					0.72
 				);
 			};
 			img.onerror = () => reject(new Error('Image load failed'));
@@ -71,10 +102,12 @@
 				canvas.toBlob(
 					(blob) => {
 						if (!blob) return reject(new Error('Canvas toBlob failed'));
-						resolve(blob);
+						// Ensure blob has correct MIME type
+						const typedBlob = new Blob([blob], { type: 'image/avif' });
+						resolve(typedBlob);
 					},
-					'image/jpeg',
-					0.92
+					'image/avif',
+					0.72
 				);
 			};
 			img.onerror = () => reject(new Error('Image load failed'));
@@ -82,42 +115,101 @@
 		});
 	}
 
-	/** Create a 250×250 thumbnail. First scale down so short side is 250px, then center-crop to 250×250 square. */
+	/** Create a 250×250 thumbnail using multi-pass downsampling for better quality. */
 	function createThumbnail(blob: Blob): Promise<Blob> {
 		return new Promise((resolve, reject) => {
 			const img = new Image();
 			img.onload = () => {
-				const targetShortSide = 250;
-				const thumbSize = 250;
-				let { width, height } = img;
+				const targetSize = 250;
+				let srcWidth = img.width;
+				let srcHeight = img.height;
+				let sourceCanvas: HTMLCanvasElement | null = null;
 
-				const shortSide = Math.min(width, height);
-				if (shortSide > targetShortSide) {
-					const scale = targetShortSide / shortSide;
-					width = Math.round(width * scale);
-					height = Math.round(height * scale);
+				// Multi-pass downsampling with tunable scale factor
+				// Lower SCALE_FACTOR (0.5) = more passes = softer/blurrier
+				// Higher SCALE_FACTOR (0.75+) = fewer passes = sharper but risking pixelation
+				// Sweet spot: 0.65-0.70
+				const SCALE_FACTOR = 0.2;
+				const STOP_THRESHOLD = targetSize * 1.1; // Stop when close enough
+
+				while (Math.min(srcWidth, srcHeight) > STOP_THRESHOLD) {
+					const scale = Math.max(SCALE_FACTOR, targetSize / Math.min(srcWidth, srcHeight));
+					const newWidth = Math.round(srcWidth * scale);
+					const newHeight = Math.round(srcHeight * scale);
+
+					const nextCanvas = document.createElement('canvas');
+					nextCanvas.width = newWidth;
+					nextCanvas.height = newHeight;
+					const nextCtx = nextCanvas.getContext('2d');
+
+					if (!nextCtx) return reject(new Error('2D context not available'));
+					nextCtx.imageSmoothingEnabled = true;
+					nextCtx.imageSmoothingQuality = 'high';
+
+					// Draw from source (either original image or previous canvas)
+					if (sourceCanvas === null) {
+						nextCtx.drawImage(img, 0, 0, newWidth, newHeight);
+					} else {
+						nextCtx.drawImage(sourceCanvas, 0, 0, newWidth, newHeight);
+					}
+
+					sourceCanvas = nextCanvas;
+					srcWidth = newWidth;
+					srcHeight = newHeight;
 				}
 
-				const canvas = document.createElement('canvas');
-				canvas.width = thumbSize;
-				canvas.height = thumbSize;
-				const ctx = canvas.getContext('2d');
-				if (!ctx) return reject(new Error('2D context not available'));
+				// Final crop to exact 250×250 square from center
+				const finalCanvas = document.createElement('canvas');
+				finalCanvas.width = targetSize;
+				finalCanvas.height = targetSize;
+				const finalCtx = finalCanvas.getContext('2d');
 
-				ctx.imageSmoothingEnabled = true;
-				ctx.imageSmoothingQuality = 'high';
+				if (!finalCtx) return reject(new Error('2D context not available'));
+				finalCtx.imageSmoothingEnabled = true;
+				finalCtx.imageSmoothingQuality = 'high';
 
-				const destX = (thumbSize - width) / 2;
-				const destY = (thumbSize - height) / 2;
-				ctx.drawImage(img, 0, 0, img.width, img.height, destX, destY, width, height);
+				// Center crop from the final source (either image or downsampled canvas)
+				if (sourceCanvas === null) {
+					// No downsampling was needed, crop directly from image
+					const offsetX = (img.width - targetSize) / 2;
+					const offsetY = (img.height - targetSize) / 2;
+					finalCtx.drawImage(
+						img,
+						offsetX,
+						offsetY,
+						targetSize,
+						targetSize,
+						0,
+						0,
+						targetSize,
+						targetSize
+					);
+				} else {
+					// Crop from the downsampled canvas
+					const offsetX = (srcWidth - targetSize) / 2;
+					const offsetY = (srcHeight - targetSize) / 2;
+					finalCtx.drawImage(
+						sourceCanvas,
+						offsetX,
+						offsetY,
+						targetSize,
+						targetSize,
+						0,
+						0,
+						targetSize,
+						targetSize
+					);
+				}
 
-				canvas.toBlob(
+				finalCanvas.toBlob(
 					(blob) => {
 						if (!blob) return reject(new Error('Canvas toBlob failed'));
-						resolve(blob);
+						// Ensure blob has correct MIME type
+						const typedBlob = new Blob([blob], { type: 'image/webp' });
+						resolve(typedBlob);
 					},
-					'image/jpeg',
-					0.92
+					'image/webp',
+					0.8
 				);
 			};
 			img.onerror = () => reject(new Error('Image load failed'));
@@ -163,7 +255,7 @@
 		return availableTags
 			.map((t) => t.toLowerCase())
 			.filter((t) => t.startsWith(q) && !tags.includes(t))
-			.slice(0, 6);
+			.slice(0, 4);
 	});
 
 	function handleTagInput(e: Event) {
@@ -175,7 +267,7 @@
 		}
 		selectedSuggestionIndex = -1;
 	}
-	
+
 	function handlePaste(e: ClipboardEvent) {
 		const value = e.clipboardData?.getData('text') || '';
 		if (value.includes(',')) {
@@ -224,10 +316,10 @@
 			}
 			return;
 		}
-		
+
 		// Handle mobile keyboard action keys
 		const isActionKey = ['Enter', 'Done', 'Go'].includes(e.key);
-		
+
 		if (isActionKey) {
 			e.preventDefault();
 		}
@@ -264,20 +356,20 @@
 				selectSuggestion(suggestions[selectedSuggestionIndex]);
 				return;
 			}
-			
+
 			// If input has text, add it as tag
 			if (input.trim()) {
 				addTag(input);
 				input = '';
 				return;
 			}
-			
+
 			// If input is empty but we have tags, show confirmation to upload
 			if (tags.length > 0) {
 				showConfirmUploadAlert = true;
 				return;
 			}
-			
+
 			return;
 		}
 
@@ -303,30 +395,42 @@
 			addTag(input);
 			input = '';
 		}
-		
+
 		if (!uploadFiles.length) return;
 		uploading = true;
 		uploadResults = [];
+		uploadStatus = {};
 		uploadProgress = 0;
 
 		const startTs = Date.now(); // timestamp of button click
 
 		for (let i = 0; i < uploadFiles.length; i++) {
 			const file = uploadFiles[i];
+			const fileKey = file.name;
 			const fd = new FormData();
 
 			try {
-				/* -------- 1. Turn whatever the user gave us into JPEG ------- */
-				const jpegBlob = await toJpegBlob(file);
+				/* -------- 1. Convert to base image format (AVIF) ------- */
+				uploadStatus[fileKey] = 'Converting to AVIF...';
+				const avifBlob = await toAvifBlob(file);
 
-				/* -------- 2. Create the two processed versions ------------- */
-				const resizedBlob = await resizeShortSide(jpegBlob);
-				const thumbBlob = await createThumbnail(jpegBlob);
+				/* -------- 2. Create the two processed versions IN PARALLEL ------- */
+				uploadStatus[fileKey] = 'Compressing...';
+				const [resizedBlob, thumbBlob] = await Promise.all([
+					resizeShortSide(avifBlob).then((blob) => {
+						uploadStatus[fileKey] = 'Full size ready';
+						return blob;
+					}),
+					createThumbnail(avifBlob).then((blob) => {
+						uploadStatus[fileKey] = 'Thumbnail ready';
+						return blob;
+					})
+				]);
 
 				/* -------- 3. Generate filenames -------------------------------- */
 				const ts = startTs - i; // 1 ms decrement per file
-				const baseName = `${ts}.jpg`;
-				const thumbName = `${ts}_thumb.jpg`;
+				const baseName = `${ts}.avif`;
+				const thumbName = `${ts}_thumb.webp`;
 
 				/* -------- 4. Attach to FormData -------------------------------- */
 				fd.append('file', resizedBlob, baseName);
@@ -336,7 +440,15 @@
 					fd.append('tags', tags.join(','));
 				}
 
+				// Debug: log what we're sending
+				console.log(`Uploading ${fileKey}:`, {
+					baseName,
+					thumbName,
+					thumbMimeType: thumbBlob.type,
+					fullMimeType: resizedBlob.type
+				});
 				/* -------- 5. Call the API ------------------------------------- */
+				uploadStatus[fileKey] = 'Uploading...';
 				const response = await fetch('/api/portfolio/images', {
 					method: 'POST',
 					headers: {
@@ -351,18 +463,21 @@
 						name: file.name,
 						error: errText || `Server error: ${response.status}`
 					});
+					uploadStatus[fileKey] = 'Failed';
 				} else {
 					const result = await response.json();
 					uploadResults.push({
 						name: file.name,
 						url: result.url
 					});
+					uploadStatus[fileKey] = 'Complete';
 				}
 			} catch (err: unknown) {
 				uploadResults.push({
 					name: file.name,
 					error: err instanceof Error ? err.message : 'Unknown error'
 				});
+				uploadStatus[fileKey] = 'Error';
 			}
 
 			uploadProgress = Math.round(((i + 1) / uploadFiles.length) * 100);
@@ -370,123 +485,276 @@
 
 		uploading = false;
 		uploadFiles = [];
+		filePreviews = [];
 	}
 </script>
 
-<Card.Root>
-	<Card.Header>
-		<div class="flex items-center justify-between">
-			<div>
-				<Card.Title>Image Upload</Card.Title>
-				<Card.Description>Upload images for the portfolio or other uses.</Card.Description>
-			</div>
-			<div class="hidden rounded-lg p-2 md:block">
-				<svg
-					xmlns="http://www.w3.org/2000/svg"
-					class="h-6 w-6"
-					viewBox="0 0 24 24"
-					fill="none"
-					stroke="currentColor"
-					stroke-width="2"
-				>
-					<rect x="3" y="3" width="18" height="18" rx="2" ry="2" />
-					<circle cx="8.5" cy="8.5" r="1.5" />
-					<polyline points="21 15 16 10 5 21" />
-				</svg>
-			</div>
-		</div>
-	</Card.Header>
-	<Card.Content class="space-y-4">
-		<FileDropZone onfiles={handleFilesDropped} accept="image/*" multiple>
-			<div class="p-6 text-center">
-				<p class="text-sm text-gray-500">Drop files here, or click to open the file picker</p>
-			</div>
-		</FileDropZone>
+<div class="space-y-6">
+	<!-- Header -->
+	<div class="mb-6">
+		<h2 class="text-2xl font-bold">Upload Images</h2>
+		<p class="mt-1 text-sm text-gray-600">
+			Add portfolio images with tags and optional descriptions
+		</p>
+	</div>
 
-		<div class="mt-4">
-			<div class="text-sm text-gray-600">Selected files ({uploadFiles.length})</div>
-			<div class="mt-2 max-h-40 space-y-2 overflow-y-auto">
-				{#each uploadFiles as f (f.name)}
-					<div class="flex items-center justify-between rounded bg-gray-50 p-2">
-						<div>{f.name} • {Math.round(f.size / 1024)}KB</div>
-						<button
-							class="text-red-500"
-							onclick={() => (uploadFiles = uploadFiles.filter((x) => x !== f))}
-						>
-							Remove
-						</button>
-					</div>
-				{/each}
+	<!-- Main Card -->
+	<Card.Root>
+		<Card.Header>
+			<div class="flex flex-col items-start justify-between gap-2 sm:flex-row sm:items-center">
+				<div>
+					<Card.Title>Drop or Select Files</Card.Title>
+					<Card.Description>Supported: JPEG, PNG, WebP, and other image formats</Card.Description>
+				</div>
 			</div>
-			{#if uploadResults.length > 0}
-				<div class="mt-4 text-sm text-gray-600">Upload Results</div>
-				<div class="mt-2 max-h-40 space-y-2 overflow-y-auto">
-					{#each uploadResults as result (result.url || result.name)}
-						<div
-							class="rounded p-2 text-xs {result.error
-								? 'bg-red-100 text-red-800'
-								: 'bg-emerald-100 text-emerald-800'}"
-						>
-							{result.name}: {result.error ? `Failed: ${result.error}` : `Success: `}<a
-								href={result.url}
-								target="_blank"
-								rel="noopener noreferrer"
-								class="underline hover:text-emerald-600">{result.url}</a
-							>
+		</Card.Header>
+
+		<Card.Content class="space-y-6">
+			<!-- File Drop Zone -->
+			<FileDropZone onfiles={handleFilesDropped} accept="image/*" multiple>
+				<div
+					class="flex flex-col items-center justify-center rounded-lg border-2 border-dashed border-gray-300 bg-gray-50 px-4 py-8 text-center transition-colors hover:border-primary hover:bg-primary/5 sm:py-12"
+				>
+					<svg
+						class="mb-3 h-8 w-8 text-gray-400"
+						xmlns="http://www.w3.org/2000/svg"
+						viewBox="0 0 24 24"
+						fill="none"
+						stroke="currentColor"
+						stroke-width="2"
+					>
+						<path d="M21 15v4a2 2 0 0 1-2 2H5a2 2 0 0 1-2-2v-4" />
+						<polyline points="17 8 12 3 7 8" />
+						<line x1="12" y1="3" x2="12" y2="15" />
+					</svg>
+					<p class="text-sm font-medium text-gray-700">Drop images here or click to browse</p>
+					<p class="mt-1 text-xs text-gray-500">Supports AVIF, PNG, JPG, WebP and other formats</p>
+				</div>
+			</FileDropZone>
+
+			<!-- Selected Files Section -->
+			{#if uploadFiles.length > 0}
+				<div class="border-t pt-6">
+					<div class="mb-4 flex items-center justify-between">
+						<div>
+							<h3 class="font-semibold text-gray-900">Ready to Upload</h3>
+							<p class="text-sm text-gray-600">
+								{uploadFiles.length}
+								{uploadFiles.length === 1 ? 'file' : 'files'} selected
+							</p>
 						</div>
-					{/each}
+						<span
+							class="inline-flex items-center rounded-full bg-blue-50 px-3 py-1 text-sm font-medium text-blue-700"
+						>
+							{uploadFiles.length} pending
+						</span>
+					</div>
+
+					<!-- File List -->
+					<div class="space-y-2">
+						{#each uploadFiles as f (f.name)}
+							{@const preview = filePreviews.find((p) => p.file === f)?.preview}
+							<div
+								class="flex items-center justify-between rounded-lg border border-gray-200 bg-white p-3 sm:p-4"
+							>
+								<div class="flex min-w-0 flex-1 items-center gap-3">
+									<div class="flex-shrink-0">
+										{#if preview}
+											<img src={preview} alt={f.name} class="h-12 w-12 rounded object-cover" />
+										{:else}
+											<div class="flex h-12 w-12 items-center justify-center rounded bg-blue-100">
+												<svg
+													class="h-6 w-6 text-blue-600"
+													xmlns="http://www.w3.org/2000/svg"
+													viewBox="0 0 24 24"
+													fill="none"
+													stroke="currentColor"
+													stroke-width="2"
+												>
+													<rect x="3" y="3" width="18" height="18" rx="2" />
+													<circle cx="8.5" cy="8.5" r="1.5" />
+													<path d="M21 15l-5-5L5 21" />
+												</svg>
+											</div>
+										{/if}
+									</div>
+									<div class="min-w-0 flex-1">
+										<p class="truncate text-sm font-medium text-gray-900">{f.name}</p>
+										<div class="flex items-center gap-2">
+											<p class="text-xs text-gray-500">{(f.size / 1024).toFixed(1)} KB</p>
+											{#if uploading && uploadStatus[f.name]}
+												<span
+													class="inline-flex items-center gap-1.5 text-xs font-medium text-blue-600"
+												>
+													<svg
+														class="h-3 w-3 animate-spin"
+														xmlns="http://www.w3.org/2000/svg"
+														viewBox="0 0 24 24"
+														fill="none"
+														stroke="currentColor"
+														stroke-width="2"
+													>
+														<circle cx="12" cy="12" r="10" opacity="0.3" />
+														<path d="M12 2A10 10 0 0 1 22 12" />
+													</svg>
+													{uploadStatus[f.name]}
+												</span>
+											{/if}
+										</div>
+									</div>
+								</div>
+								<button
+									type="button"
+									onclick={() => (uploadFiles = uploadFiles.filter((x) => x !== f))}
+									class="ml-2 flex-shrink-0 rounded p-1 text-gray-400 transition-colors hover:bg-red-50 hover:text-red-600 focus:ring-2 focus:ring-red-500 focus:ring-offset-2 focus:outline-none"
+									aria-label="Remove {f.name}"
+								>
+									<svg
+										class="h-5 w-5"
+										xmlns="http://www.w3.org/2000/svg"
+										viewBox="0 0 24 24"
+										fill="none"
+										stroke="currentColor"
+										stroke-width="2"
+									>
+										<path d="M18 6l-12 12" />
+										<path d="M6 6l12 12" />
+									</svg>
+								</button>
+							</div>
+						{/each}
+					</div>
 				</div>
 			{/if}
-		</div>
 
-		<div class="space-y-1">
-			<label for="tag-input" class="text-sm font-medium text-gray-700">Tags</label>
-
-			<div class="relative">
-				<div
-					class="flex min-h-[44px] w-full flex-wrap gap-1.5 rounded-md border border-input bg-background px-3 py-2 text-sm ring-offset-background focus-within:ring-2 focus-within:ring-ring focus-within:ring-offset-2 focus-within:outline-none"
-				>
-					{#each tags as tag (tag)}
-						<span
-							class="flex items-center gap-1 rounded-full px-2 py-1 text-xs
-							{isSemantic(tag) ? 'bg-indigo-100 text-indigo-800' : 'bg-emerald-100 text-emerald-800'}"
-						>
-							{tag}
-
-							<button
-								type="button"
-								class="ml-0.5 flex h-4 w-4 items-center justify-center rounded-full leading-none
-								{isSemantic(tag)
-									? 'text-indigo-700 hover:bg-indigo-200'
-									: 'text-emerald-700 hover:bg-emerald-200'}"
-								onclick={() => removeTag(tag)}
-								aria-label={`Remove ${tag}`}
+			<!-- Upload Results Section -->
+			{#if uploadResults.length > 0}
+				<div class="border-t pt-6">
+					<h3 class="mb-4 font-semibold text-gray-900">Upload Results</h3>
+					<div class="space-y-2">
+						{#each uploadResults as result (result.url || result.name)}
+							<div
+								class="rounded-lg border p-3 sm:p-4"
+								class:bg-red-50={result.error}
+								class:border-red-200={result.error}
+								class:bg-green-50={!result.error}
+								class:border-green-200={!result.error}
 							>
-								×
-							</button>
-						</span>
-					{/each}
-
-					<input
-						type="search"
-						maxlength={256}
-						enterkeyhint="done"
-						autocomplete="off"
-						autocorrect="off"
-						autocapitalize="off"
-						spellcheck="false"
-						class="min-w-[100px] flex-1 border-none bg-transparent text-sm outline-none placeholder:text-muted-foreground"
-						bind:this={inputRef}
-						bind:value={input}
-						onkeydown={handleKey}
-						oninput={handleTagInput}
-						onpaste={handlePaste}
-						placeholder={tags.length ? '' : 'Add tags…'}
-					/>
+								<div class="flex items-start gap-3">
+									<div class="flex-shrink-0 pt-0.5">
+										{#if result.error}
+											<svg
+												class="h-5 w-5 text-red-600"
+												xmlns="http://www.w3.org/2000/svg"
+												viewBox="0 0 24 24"
+												fill="none"
+												stroke="currentColor"
+												stroke-width="2"
+											>
+												<circle cx="12" cy="12" r="10" />
+												<line x1="12" y1="8" x2="12" y2="12" />
+												<line x1="12" y1="16" x2="12.01" y2="16" />
+											</svg>
+										{:else}
+											<svg
+												class="h-5 w-5 text-green-600"
+												xmlns="http://www.w3.org/2000/svg"
+												viewBox="0 0 24 24"
+												fill="none"
+												stroke="currentColor"
+												stroke-width="2"
+											>
+												<path d="M22 11.08V12a10 10 0 1 1-5.93-9.14" />
+												<polyline points="22 4 12 14.01 9 11.01" />
+											</svg>
+										{/if}
+									</div>
+									<div class="min-w-0 flex-1">
+										<p
+											class="truncate text-sm font-medium {result.error
+												? 'text-red-900'
+												: 'text-green-900'}"
+										>
+											{result.name}
+										</p>
+										{#if result.error}
+											<p class="mt-1 text-xs text-red-700">{result.error}</p>
+										{:else}
+											<a
+												href={result.url}
+												target="_blank"
+												rel="noopener noreferrer"
+												class="mt-1 inline-block text-xs text-green-700 underline hover:text-green-900"
+											>
+												View uploaded image →
+											</a>
+										{/if}
+									</div>
+								</div>
+							</div>
+						{/each}
+					</div>
 				</div>
+			{/if}
+
+			<!-- Tags Section -->
+			<div class="border-t pt-6">
+				<label for="tag-input" class="block text-sm font-semibold text-gray-900">Add Tags</label>
+				<p class="mt-1 text-xs text-gray-600">
+					Searchable tags help organize images. Use <code class="rounded bg-gray-100 px-1 py-0.5"
+						>category:value</code
+					> format.
+				</p>
+
+				<div class="relative">
+					<div class="flex gap-2">
+						<div
+							class="flex min-h-[44px] w-full flex-wrap gap-2 rounded-lg border border-gray-300 bg-white px-3 py-2 text-sm transition-colors focus-within:border-primary focus-within:ring-2 focus-within:ring-primary/10 focus-within:outline-none"
+						>
+							{#each tags as tag (tag)}
+								<span
+									class="inline-flex items-center gap-1.5 rounded-full px-2.5 py-1 text-xs font-medium transition-colors"
+									class:bg-indigo-100={isSemantic(tag)}
+									class:text-indigo-800={isSemantic(tag)}
+									class:bg-emerald-100={!isSemantic(tag)}
+									class:text-emerald-800={!isSemantic(tag)}
+								>
+									{tag}
+									<button
+										type="button"
+										onclick={() => removeTag(tag)}
+										class="inline-flex h-4 w-4 items-center justify-center rounded-full leading-none transition-colors hover:opacity-80 focus:ring-2 focus:ring-offset-2 focus:outline-none"
+										class:text-indigo-700={isSemantic(tag)}
+										class:focus:ring-indigo-500={isSemantic(tag)}
+										class:text-emerald-700={!isSemantic(tag)}
+										class:focus:ring-emerald-500={!isSemantic(tag)}
+										aria-label="Remove {tag}"
+									>
+										×
+									</button>
+								</span>
+							{/each}
+
+							<input
+								type="search"
+								maxlength={256}
+								enterkeyhint="done"
+								autocomplete="off"
+								autocorrect="off"
+								autocapitalize="off"
+								spellcheck="false"
+								class="min-w-[100px] flex-1 border-none bg-transparent text-sm outline-none placeholder:text-gray-500"
+								bind:this={inputRef}
+								bind:value={input}
+								onkeydown={handleKey}
+								oninput={handleTagInput}
+								onpaste={handlePaste}
+								placeholder={tags.length ? '' : 'Add tags…'}
+							/>
+						</div>
 
 				{#if input.length && suggestions.length}
-					<div class="absolute right-0 left-0 z-10 mt-1 rounded-md border bg-white shadow-md">
+				<div class="absolute left-0 right-0 top-full z-10 mt-1 rounded-md border bg-white shadow-md">
 						{#each suggestions as s, i (s)}
 							{@const isHighlighted = isMobile ? i === 0 : i === selectedSuggestionIndex}
 							<div
@@ -503,36 +771,74 @@
 						{/each}
 					</div>
 				{/if}
-			</div>
+					</div>
+				</div>
 
-			<p class="text-xs text-gray-500">
-				Add searchable tags here such as <code>`scooby doo`</code> or filterable categories like
-				<code>`style:french`</code>
-				or
-				<code>`colour:green`</code>
-			</p>
-		</div>
-		<div class="flex items-center justify-end gap-2">
-			<Button onclick={uploadOneOrMany} disabled={!uploadFiles.length || uploading}>
-				{uploading ? `Uploading (${uploadProgress}%)` : 'Upload Selected Files'}
-			</Button>
-		</div>
-	</Card.Content>
-</Card.Root>
+				<!-- Action Buttons -->
+				<div class="border-t pt-6">
+					<div class="flex justify-end">
+						<Button onclick={uploadOneOrMany} disabled={!uploadFiles.length || uploading}>
+							{#if uploading}
+								<svg
+									class="mr-2 h-4 w-4 animate-spin"
+									xmlns="http://www.w3.org/2000/svg"
+									viewBox="0 0 24 24"
+									fill="none"
+									stroke="currentColor"
+									stroke-width="2"
+								>
+									<circle cx="12" cy="12" r="10" opacity="0.3" />
+									<path d="M12 2A10 10 0 0 1 22 12" />
+								</svg>
+								Uploading ({uploadProgress}%)
+							{:else}
+								<svg
+									class="mr-2 h-4 w-4"
+									xmlns="http://www.w3.org/2000/svg"
+									viewBox="0 0 24 24"
+									fill="none"
+									stroke="currentColor"
+									stroke-width="2"
+								>
+									<path d="M21 15v4a2 2 0 0 1-2 2H5a2 2 0 0 1-2-2v-4" />
+									<polyline points="17 8 12 3 7 8" />
+									<line x1="12" y1="3" x2="12" y2="15" />
+								</svg>
+								Upload {uploadFiles.length > 1 ? uploadFiles.length + ' Files' : 'File'}
+							{/if}
+						</Button>
+					</div>
+				</div>
+			</div></Card.Content
+		>
+	</Card.Root>
 
-<AlertDialog.Root bind:open={showConfirmUploadAlert}>
-	<AlertDialog.Content class="z-[60]">
-		<AlertDialog.Header>
-			<AlertDialog.Title>Upload with {tags.length} tag{tags.length === 1 ? '' : 's'}?</AlertDialog.Title>
-			<AlertDialog.Description>
-				You have {tags.length} tag{tags.length === 1 ? '' : 's'} selected:
-				<span class="font-medium">{tags.join(', ')}</span>. 
-				Ready to upload {uploadFiles.length} file{uploadFiles.length === 1 ? '' : 's'}?
-			</AlertDialog.Description>
-		</AlertDialog.Header>
-		<AlertDialog.Footer>
-			<AlertDialog.Cancel>Cancel</AlertDialog.Cancel>
-			<AlertDialog.Action onclick={uploadOneOrMany}>Upload</AlertDialog.Action>
-		</AlertDialog.Footer>
-	</AlertDialog.Content>
-</AlertDialog.Root>
+	<!-- Confirmation Dialog -->
+	<AlertDialog.Root bind:open={showConfirmUploadAlert}>
+		<AlertDialog.Content class="z-[60]">
+			<AlertDialog.Header>
+				<AlertDialog.Title>Confirm Upload</AlertDialog.Title>
+				<AlertDialog.Description>
+					You're about to upload {uploadFiles.length}
+					{uploadFiles.length === 1 ? 'file' : 'files'} with {tags.length}
+					{tags.length === 1 ? 'tag' : 'tags'}.
+					{#if tags.length > 0}
+						<div class="mt-3 flex flex-wrap gap-2">
+							{#each tags as tag}
+								<span
+									class="inline-block rounded-full bg-gray-200 px-2.5 py-1 text-xs text-gray-800"
+								>
+									{tag}
+								</span>
+							{/each}
+						</div>
+					{/if}
+				</AlertDialog.Description>
+			</AlertDialog.Header>
+			<AlertDialog.Footer>
+				<AlertDialog.Cancel>Cancel</AlertDialog.Cancel>
+				<AlertDialog.Action onclick={uploadOneOrMany}>Upload Now</AlertDialog.Action>
+			</AlertDialog.Footer>
+		</AlertDialog.Content>
+	</AlertDialog.Root>
+</div>
diff --git a/frontend/src/routes/portfolio/+page.svelte b/frontend/src/routes/portfolio/+page.svelte
index 5e86d0c..cb1eada 100644
--- a/frontend/src/routes/portfolio/+page.svelte
+++ b/frontend/src/routes/portfolio/+page.svelte
@@ -275,6 +275,20 @@
 
 	function clearFilters() {
 		selectedFilters = {};
+		offset = 0;
+
+		// Build URL with reactive page state
+		const url = new URL(page.url);
+		const keysToDelete = Array.from(url.searchParams.keys()).filter((k) => k.startsWith('filter['));
+		keysToDelete.forEach((k) => url.searchParams.delete(k));
+		// eslint-disable-next-line svelte/no-navigation-without-resolve
+		goto(url.pathname + url.search, { replaceState: true, noScroll: true });
+
+		fetchImages(false);
+		fetchFilters();
+	}
+
+	function clearSearch() {
 		selectedTag = '';
 		selectedTags = [];
 		searchQuery = '';
@@ -284,13 +298,10 @@
 		const url = new URL(page.url);
 		url.searchParams.delete('tag');
 		url.searchParams.delete('tags');
-		const keysToDelete = Array.from(url.searchParams.keys()).filter((k) => k.startsWith('filter['));
-		keysToDelete.forEach((k) => url.searchParams.delete(k));
 		// eslint-disable-next-line svelte/no-navigation-without-resolve
 		goto(url.pathname + url.search, { replaceState: true, noScroll: true });
 
 		fetchImages(false);
-		fetchFilters();
 	}
 
 	let sentinelRef: HTMLDivElement | undefined = $state(undefined);
@@ -614,6 +625,27 @@
 				<Button onclick={applySearch}>
 					{loading ? 'Searching...' : 'Search'}
 				</Button>
+
+			{#if selectedTag || selectedTags.length > 0}
+				<button
+					class="flex shrink-0 items-center justify-center"
+					onclick={clearSearch}
+					aria-label="Clear search tags"
+				>
+					<div
+						class="flex h-6 w-6 items-center justify-center rounded-full bg-red-100 text-red-600 hover:bg-red-200"
+					>
+						<svg class="h-3.5 w-3.5" fill="none" stroke="currentColor" viewBox="0 0 24 24">
+							<path
+								stroke-linecap="round"
+								stroke-linejoin="round"
+								stroke-width="2"
+								d="M6 18L18 6M6 6l12 12"
+							/>
+						</svg>
+					</div>
+				</button>
+			{/if}
 			</div>
 		</div>
 	</div>