diff --git a/src/main/resources/static/css/styles.css b/src/main/resources/static/css/styles.css
index 08dd981..7b23dab 100644
--- a/src/main/resources/static/css/styles.css
+++ b/src/main/resources/static/css/styles.css
@@ -537,6 +537,59 @@ body {
     margin: 6px 0;
 }
 
+.upload-row {
+    display: flex;
+    align-items: center;
+    gap: 10px;
+    margin: 12px 0 4px;
+}
+
+.file-input-field {
+    display: none;
+}
+
+.file-input-trigger {
+    flex: 1;
+    display: inline-flex;
+    align-items: center;
+    gap: 12px;
+    padding: 10px 12px;
+    border: 1px dashed rgba(124, 58, 237, 0.45);
+    border-radius: 10px;
+    background: rgba(124, 58, 237, 0.08);
+    cursor: pointer;
+    transition: border-color 120ms ease, background 120ms ease;
+}
+
+.file-input-trigger:hover {
+    border-color: rgba(124, 58, 237, 0.8);
+    background: rgba(124, 58, 237, 0.14);
+}
+
+.file-input-icon {
+    width: 38px;
+    height: 38px;
+    border-radius: 8px;
+    display: grid;
+    place-items: center;
+    background: rgba(124, 58, 237, 0.16);
+    color: #c4b5fd;
+}
+
+.file-input-copy {
+    display: flex;
+    flex-direction: column;
+    gap: 4px;
+}
+
+.file-input-copy strong {
+    font-size: 14px;
+}
+
+.file-input-copy small {
+    color: #cbd5e1;
+}
+
 .title-row {
     display: flex;
     align-items: center;
diff --git a/src/main/resources/static/js/admin.js b/src/main/resources/static/js/admin.js
index adf8d0c..685072e 100644
--- a/src/main/resources/static/js/admin.js
+++ b/src/main/resources/static/js/admin.js
@@ -28,6 +28,7 @@ const muteInput = document.getElementById('asset-muted');
 const selectedZLabel = document.getElementById('asset-z-level');
 const playbackSection = document.getElementById('playback-section');
 const controlsPlaceholder = document.getElementById('asset-controls-placeholder');
+const fileNameLabel = document.getElementById('asset-file-name');
 const aspectLockState = new Map();
 const commitSizeChange = debounce(() => applyTransformFromInputs(), 180);
 
@@ -102,8 +103,10 @@ function renderAssets(list) {
 function storeAsset(asset) {
     if (!asset) return;
     asset.zIndex = Math.max(1, asset.zIndex ?? 1);
-    if (asset.createdAt && typeof asset.createdAtMs === 'undefined') {
-        asset.createdAtMs = new Date(asset.createdAt).getTime();
+    const parsedCreatedAt = asset.createdAt ? new Date(asset.createdAt).getTime() : NaN;
+    const hasCreatedAtMs = typeof asset.createdAtMs === 'number' && Number.isFinite(asset.createdAtMs);
+    if (!hasCreatedAtMs) {
+        asset.createdAtMs = Number.isFinite(parsedCreatedAt) ? parsedCreatedAt : Date.now();
     }
     assets.set(asset.id, asset);
     zOrderDirty = true;
@@ -177,6 +180,10 @@ function zComparator(a, b) {
     return (a?.createdAtMs || 0) - (b?.createdAtMs || 0);
 }
 
+function getChronologicalAssets() {
+    return Array.from(assets.values()).sort((a, b) => (a?.createdAtMs || 0) - (b?.createdAtMs || 0));
+}
+
 function drawAsset(asset) {
     const renderState = smoothState(asset);
     const halfWidth = renderState.width / 2;
@@ -626,7 +633,7 @@ function renderAssetList() {
         return;
     }
 
-    const sortedAssets = getZOrderedAssets().reverse();
+    const sortedAssets = getChronologicalAssets();
     sortedAssets.forEach((asset) => {
         const li = document.createElement('li');
         li.className = 'asset-item';
@@ -854,7 +861,7 @@ function recenterSelectedAsset() {
 function bringForward() {
     const asset = getSelectedAsset();
     if (!asset) return;
-    const ordered = getZOrderedAssets();
+    const ordered = [...getZOrderedAssets()];
     const index = ordered.findIndex((item) => item.id === asset.id);
     if (index === -1 || index === ordered.length - 1) return;
     [ordered[index], ordered[index + 1]] = [ordered[index + 1], ordered[index]];
@@ -864,7 +871,7 @@ function bringForward() {
 function bringBackward() {
     const asset = getSelectedAsset();
     if (!asset) return;
-    const ordered = getZOrderedAssets();
+    const ordered = [...getZOrderedAssets()];
     const index = ordered.findIndex((item) => item.id === asset.id);
     if (index <= 0) return;
     [ordered[index], ordered[index - 1]] = [ordered[index - 1], ordered[index]];
@@ -987,6 +994,14 @@ function deleteAsset(asset) {
     });
 }
 
+function handleFileSelection(input) {
+    if (!input) return;
+    const name = input.files && input.files.length ? input.files[0].name : '';
+    if (fileNameLabel) {
+        fileNameLabel.textContent = name || 'No file chosen';
+    }
+}
+
 function uploadAsset() {
     const fileInput = document.getElementById('asset-file');
     if (!fileInput || !fileInput.files || fileInput.files.length === 0) {
@@ -1000,6 +1015,7 @@ function uploadAsset() {
         body: data
     }).then(() => {
         fileInput.value = '';
+        handleFileSelection(fileInput);
     });
 }
 
@@ -1027,7 +1043,7 @@ function isPointOnAsset(asset, x, y) {
 }
 
 function findAssetAtPoint(x, y) {
-    const ordered = getZOrderedAssets().reverse();
+    const ordered = [...getZOrderedAssets()].reverse();
     return ordered.find((asset) => isPointOnAsset(asset, x, y)) || null;
 }
 
diff --git a/src/main/resources/templates/admin.html b/src/main/resources/templates/admin.html
index 66edf6d..4d79ee4 100644
--- a/src/main/resources/templates/admin.html
+++ b/src/main/resources/templates/admin.html
@@ -27,8 +27,17 @@
         <div class="controls-full panel">
             <h3>Overlay assets</h3>
             <p>Upload overlay visuals and adjust them inline.</p>
-            <input id="asset-file" type="file" accept="image/*,video/*" />
-            <button onclick="uploadAsset()">Upload</button>
+            <div class="upload-row">
+                <input id="asset-file" class="file-input-field" type="file" accept="image/*,video/*" onchange="handleFileSelection(this)" />
+                <label for="asset-file" class="file-input-trigger">
+                    <span class="file-input-icon"><i class="fa-solid fa-cloud-arrow-up"></i></span>
+                    <span class="file-input-copy">
+                        <strong>Select an image, GIF, or video</strong>
+                        <small id="asset-file-name">No file chosen</small>
+                    </span>
+                </label>
+                <button onclick="uploadAsset()">Upload</button>
+            </div>
             <ul id="asset-list" class="asset-list"></ul>
             <div id="asset-controls-placeholder" class="hidden"></div>
             <div id="asset-controls" class="hidden asset-settings">