diff --git a/CLAUDE.md b/CLAUDE.md
index 8496129..b3dba64 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -19,7 +19,9 @@ The binary does three things at once:
 - Serves a multipart upload API at `POST /upload`
 - In dev mode (`--serve`), also serves `public/` as static files
 
-Routes: `GET /upload` (HTML upload form), `POST /upload` (multipart),
+Routes: `GET /upload` (HTML upload form — multi-photo: the page posts one
+`POST /upload` per selected photo, each with its own caption/date/tags),
+`POST /upload` (multipart, one image per request),
 `GET /manage` (edit/delete UI), the manage API under `/api/` (see Manage),
 `GET /health`. Every route except `/health` is gated by HTTP Basic auth when
 `-htpasswd` is set (see Auth).
diff --git a/README.md b/README.md
index f832d4d..81be958 100644
--- a/README.md
+++ b/README.md
@@ -24,7 +24,7 @@ database, no framework.
 
 **Content & management (no database)**
 - `.toml` sidecars are the source of truth; the binary watches the content dir and rebuilds on any change. Four renditions per photo (original, 600² thumbnail, 1600px medium, 1200px OG), each skipped when already up to date.
-- **Web upload** (`/upload`) with EXIF-date prefill and tag autocomplete.
+- **Web upload** (`/upload`): pick one or many photos, each with its own EXIF-prefilled date, caption and tag-autocompleting tags field; posted with per-photo status and retry.
 - **Manage UI** (`/manage`): edit caption/date/tags, bulk tag add/remove, and delete — delete is reversible (moves to `content/.trash/`, with restore / empty).
 - Tag autocomplete across the upload and manage forms, fed by `/tags.json`.
 
diff --git a/templates/upload.html b/templates/upload.html
index 681eb3c..2d5fcc8 100644
--- a/templates/upload.html
+++ b/templates/upload.html
@@ -10,177 +10,219 @@
   <link rel="icon" type="image/png" href="/static/web-32.png" sizes="32x32">
   <link rel="apple-touch-icon" href="/static/web-192.png">
   <style>
-    .upload-page {
-      max-width: 520px;
-      margin: 0 auto;
-      padding: 32px 20px;
-    }
+    .upload-page { max-width: 640px; margin: 0 auto; padding: 32px 20px 80px; }
     .upload-page h2 {
-      font-family: var(--serif);
-      font-size: 22px;
-      font-weight: 600;
-      color: var(--fg);
-      margin-bottom: 28px;
+      font-family: var(--serif); font-size: 22px; font-weight: 600;
+      color: var(--fg); margin-bottom: 20px;
     }
-    .drop-zone {
-      border: 1px dashed var(--bg2);
-      background: var(--bg0);
-      width: 100%;
-      aspect-ratio: 1;
-      max-height: 340px;
-      display: flex;
-      flex-direction: column;
-      align-items: center;
-      justify-content: center;
-      cursor: pointer;
-      margin-bottom: 24px;
-      position: relative;
-      overflow: hidden;
-      transition: border-color 0.2s;
+    .pick-btn, .submit-btn {
+      width: 100%; background: var(--bg1); border: 1px solid var(--bg2);
+      color: var(--fg2); font-family: var(--serif); font-size: 16px; font-weight: 600;
+      padding: 12px; cursor: pointer; transition: background .2s, color .2s;
     }
-    .drop-zone:hover { border-color: var(--fg4); }
-    .drop-zone.has-image { border-style: solid; border-color: var(--bg2); }
-    .drop-zone input[type="file"] {
-      position: absolute;
-      inset: 0;
-      opacity: 0;
-      cursor: pointer;
-      width: 100%;
-      height: 100%;
+    .pick-btn:hover:not(:disabled), .submit-btn:hover:not(:disabled) { background: var(--bg2); color: var(--fg); }
+    .submit-btn:disabled { opacity: .35; cursor: not-allowed; }
+    .pick-btn { margin-bottom: 20px; }
+    #file-input { display: none; }
+
+    #empty {
+      display: flex; align-items: center; justify-content: center;
+      height: 140px; background: var(--bg0); color: var(--fg4);
+      font-family: var(--serif); margin-bottom: 20px;
     }
-    .drop-prompt {
-      display: flex;
-      flex-direction: column;
-      align-items: center;
-      gap: 10px;
-      color: var(--fg4);
-      pointer-events: none;
+
+    .card { display: grid; grid-template-columns: 84px 1fr auto; gap: 14px; align-items: start; padding: 14px 0; border-top: 1px solid var(--bg1); }
+    .card .thumb { width: 84px; height: 84px; background: var(--bg1); object-fit: cover; display: block; }
+    .card .fields { display: flex; flex-direction: column; gap: 8px; min-width: 0; }
+    .card input {
+      width: 100%; box-sizing: border-box; background: var(--bg0);
+      border: 1px solid var(--bg2); color: var(--fg); font-size: 15px; padding: 8px 10px; outline: none;
     }
-    .drop-prompt p  { font-size: 14px; font-family: var(--serif); }
-    .drop-prompt small { font-size: 12px; font-family: monospace; }
-    #preview {
-      display: none;
-      position: absolute;
-      inset: 0;
-      width: 100%;
-      height: 100%;
-      object-fit: cover;
-      pointer-events: none;
+    .card input[type="text"] { font-family: var(--serif); }
+    .card input[type="date"] { font-family: monospace; font-size: 13px; color-scheme: dark; width: auto; }
+    .card input:focus { border-color: var(--fg4); }
+    .card input:disabled { opacity: .5; }
+    .c-remove {
+      background: none; border: none; color: var(--fg4); font-size: 16px; cursor: pointer; padding: 4px;
     }
-    .change-hint {
-      display: none;
-      position: absolute;
-      inset: auto 0 0 0;
-      padding: 6px 10px;
-      background: rgba(29, 32, 33, 0.75);
-      color: var(--fg2);
-      font-family: monospace;
-      font-size: 11px;
-      text-transform: uppercase;
-      letter-spacing: 0.08em;
-      text-align: center;
-      pointer-events: none;
-    }
-    .drop-zone.has-image .change-hint { display: block; }
-    .field { margin-bottom: 18px; }
-    .field label {
-      display: block;
-      font-size: 12px;
-      color: var(--fg4);
-      font-family: monospace;
-      text-transform: uppercase;
-      letter-spacing: 0.06em;
-      margin-bottom: 6px;
-    }
-    .field input[type="text"],
-    .field input[type="date"] {
-      width: 100%;
-      background: var(--bg0);
-      border: 1px solid var(--bg2);
-      color: var(--fg);
-      font-size: 16px;
-      padding: 10px 12px;
-      outline: none;
-      transition: border-color 0.2s;
-    }
-    .field input[type="text"]  { font-family: var(--serif); }
-    .field input[type="date"]  { font-family: monospace; font-size: 14px; color-scheme: dark; }
-    .field input:focus { border-color: var(--fg4); }
-    .submit-btn {
-      width: 100%;
-      background: var(--bg1);
-      border: 1px solid var(--bg2);
-      color: var(--fg2);
-      font-family: var(--serif);
-      font-size: 16px;
-      font-weight: 600;
-      padding: 12px;
-      cursor: pointer;
-      transition: background 0.2s, color 0.2s;
-    }
-    .submit-btn:hover:not(:disabled) { background: var(--bg2); color: var(--fg); }
-    .submit-btn:disabled { opacity: 0.35; cursor: not-allowed; }
-    #feedback {
-      display: none;
-      margin-top: 14px;
-      font-size: 13px;
-      font-family: monospace;
-      padding: 10px 12px;
-    }
-    #feedback.ok  { display: block; background: #1d2e1d; color: #b8bb26; border: 1px solid #344d28; }
-    #feedback.err { display: block; background: #2e1d1d; color: #fb4934; border: 1px solid #5a2828; }
+    .c-status { font-family: monospace; font-size: 12px; min-height: 16px; }
+    .c-status.ok  { color: #b8bb26; }
+    .c-status.err { color: #fb4934; }
+    .c-status.up  { color: var(--fg4); }
+    .c-status a { color: #8ec07c; }
+
+    #bar { margin-top: 20px; }
+    #summary { margin-top: 12px; font-family: monospace; font-size: 13px; color: var(--fg4); }
   </style>
 </head>
 <body>
   <div class="upload-page">
     <a href="/" class="back-btn">← Gallery</a>
-    <h2>Upload photo</h2>
+    <h2>Upload photos</h2>
 
-    <div class="drop-zone" id="drop-zone">
-      <input type="file" id="file-input" accept=".jpg,.jpeg,.png" aria-label="Choose photo">
-      <div class="drop-prompt" id="prompt">
-        <svg width="40" height="40" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="1" aria-hidden="true">
-          <rect x="3" y="3" width="18" height="18" rx="1"/>
-          <circle cx="8.5" cy="8.5" r="1.5"/>
-          <path d="M21 15l-5-5L5 21"/>
-        </svg>
-        <p>Click to choose a photo</p>
-        <small>jpg or png</small>
-      </div>
-      <img id="preview" alt="Preview">
-      <div class="change-hint">Click to change</div>
+    <input type="file" id="file-input" accept=".jpg,.jpeg,.png" multiple>
+    <button class="pick-btn" id="pick-btn">Choose photos</button>
+
+    <div id="empty">No photos selected</div>
+    <div id="list"></div>
+
+    <div id="bar" style="display:none">
+      <button class="submit-btn" id="post-btn">Post photos</button>
+      <div id="summary"></div>
     </div>
-
-    <div class="field">
-      <label for="caption">Caption</label>
-      <input type="text" id="caption" placeholder="Describe the photo" autocomplete="off">
-    </div>
-
-    <div class="field">
-      <label for="date">Date</label>
-      <input type="date" id="date">
-    </div>
-
-    <div class="field">
-      <label for="tags">Tags</label>
-      <input type="text" id="tags" placeholder="comma-separated, lowercase" autocomplete="off" data-tagcomplete>
-    </div>
-
-    <button class="submit-btn" id="submit-btn" disabled>Upload photo</button>
-    <div id="feedback"></div>
   </div>
 
   <script src="/static/tagcomplete.js"></script>
   <script>
     const fileInput = document.getElementById('file-input');
-    const preview   = document.getElementById('preview');
-    const prompt    = document.getElementById('prompt');
-    const dropZone  = document.getElementById('drop-zone');
-    const submitBtn = document.getElementById('submit-btn');
-    const feedback  = document.getElementById('feedback');
-    const dateInput = document.getElementById('date');
+    const pickBtn   = document.getElementById('pick-btn');
+    const list      = document.getElementById('list');
+    const emptyEl   = document.getElementById('empty');
+    const bar       = document.getElementById('bar');
+    const postBtn   = document.getElementById('post-btn');
+    const summary   = document.getElementById('summary');
 
-    dateInput.value = new Date().toISOString().slice(0, 10);
+    // One entry per chosen photo. status: pending | uploading | ok | error.
+    let items = [];
+    let seq = 0;
+    let posting = false;
+
+    pickBtn.addEventListener('click', () => fileInput.click());
+    fileInput.addEventListener('change', () => {
+      for (const file of fileInput.files) addItem(file);
+      fileInput.value = ''; // allow re-choosing the same file
+      refresh();
+    });
+
+    function addItem(file) {
+      const item = { id: ++seq, file, status: 'pending', el: null };
+      items.push(item);
+      item.el = buildCard(item);
+      list.appendChild(item.el);
+      // Preview.
+      const url = URL.createObjectURL(file);
+      const img = item.el.querySelector('.thumb');
+      img.onload = () => URL.revokeObjectURL(url);
+      img.src = url;
+      // Prefill date from EXIF, else file mtime.
+      prefillDate(item, file);
+      // Tag autocomplete on this card's tags field.
+      if (window.TagComplete) window.TagComplete.attach(item.el.querySelector('.c-tags'));
+    }
+
+    function buildCard(item) {
+      const el = document.createElement('div');
+      el.className = 'card';
+      el.innerHTML = `
+        <img class="thumb" alt="">
+        <div class="fields">
+          <input type="text" class="c-caption" placeholder="Caption" autocomplete="off">
+          <input type="date" class="c-date">
+          <input type="text" class="c-tags" placeholder="tags, comma-separated" autocomplete="off">
+          <div class="c-status"></div>
+        </div>
+        <button class="c-remove" title="Remove">✕</button>`;
+      el.querySelector('.c-remove').addEventListener('click', () => removeItem(item.id));
+      return el;
+    }
+
+    async function prefillDate(item, file) {
+      let d = null;
+      try { d = await readExifDate(file); } catch (_) {}
+      if (!d && file.lastModified) d = new Date(file.lastModified).toISOString().slice(0, 10);
+      if (!d) d = new Date().toISOString().slice(0, 10);
+      item.el.querySelector('.c-date').value = d;
+    }
+
+    function removeItem(id) {
+      const item = items.find((i) => i.id === id);
+      if (!item || item.status === 'uploading') return;
+      item.el.remove();
+      items = items.filter((i) => i.id !== id);
+      refresh();
+    }
+
+    function refresh() {
+      const has = items.length > 0;
+      emptyEl.style.display = has ? 'none' : 'flex';
+      bar.style.display = has ? 'block' : 'none';
+      pickBtn.textContent = has ? 'Add more photos' : 'Choose photos';
+      updateButton();
+    }
+
+    function pending() { return items.filter((i) => i.status !== 'ok'); }
+
+    function updateButton() {
+      const n = pending().length;
+      postBtn.disabled = posting || n === 0;
+      postBtn.textContent = posting
+        ? 'Posting…'
+        : n === 0 ? 'All posted' : (n === 1 ? 'Post 1 photo' : `Post ${n} photos`);
+    }
+
+    function setStatus(item, cls, html) {
+      const s = item.el.querySelector('.c-status');
+      s.className = 'c-status ' + cls;
+      s.innerHTML = html;
+    }
+
+    function setDisabled(item, disabled) {
+      item.el.querySelectorAll('input').forEach((i) => (i.disabled = disabled));
+      item.el.querySelector('.c-remove').disabled = disabled;
+    }
+
+    async function postOne(item) {
+      item.status = 'uploading';
+      setDisabled(item, true);
+      setStatus(item, 'up', 'Uploading…');
+
+      const form = new FormData();
+      form.append('image', item.file);
+      form.append('caption', item.el.querySelector('.c-caption').value);
+      form.append('date', item.el.querySelector('.c-date').value);
+      form.append('tags', item.el.querySelector('.c-tags').value);
+
+      try {
+        const res = await fetch('/upload', { method: 'POST', body: form });
+        const text = (await res.text()).trim();
+        if (res.ok) {
+          item.status = 'ok';
+          const slug = text.replace(/^uploaded\s+/, '').replace(/\.[^.]+$/, '');
+          setStatus(item, 'ok', '✓ posted · <a href="/photo/' + encodeURIComponent(slug) + '/" target="_blank" rel="noopener">view</a>');
+        } else {
+          item.status = 'error';
+          setDisabled(item, false);
+          setStatus(item, 'err', '✗ ' + (text || res.status));
+        }
+      } catch (err) {
+        item.status = 'error';
+        setDisabled(item, false);
+        setStatus(item, 'err', '✗ ' + err.message);
+      }
+    }
+
+    postBtn.addEventListener('click', async () => {
+      if (posting) return;
+      posting = true;
+      updateButton();
+      if (window.TagComplete) window.TagComplete.invalidate();
+
+      // Sequential: gentler on mobile connections, and the rebuild is debounced
+      // server-side anyway.
+      const todo = pending();
+      let done = 0;
+      for (const item of todo) {
+        await postOne(item);
+        done++;
+        summary.textContent = `${done}/${todo.length} processed`;
+      }
+
+      posting = false;
+      const ok = items.filter((i) => i.status === 'ok').length;
+      const failed = items.filter((i) => i.status === 'error').length;
+      summary.textContent = `${ok} posted` + (failed ? `, ${failed} failed (press Post to retry)` : '');
+      updateButton();
+    });
 
     // Read DateTimeOriginal from a JPEG's EXIF APP1 segment. Returns "YYYY-MM-DD"
     // or null if the file isn't a JPEG, has no EXIF, or lacks the tag.
@@ -228,68 +270,6 @@
       }
       return null;
     }
-
-    fileInput.addEventListener('change', async () => {
-      const file = fileInput.files[0];
-      if (!file) return;
-      const url = URL.createObjectURL(file);
-      preview.onload = () => URL.revokeObjectURL(url);
-      preview.src = url;
-      preview.style.display = 'block';
-      prompt.style.display  = 'none';
-      dropZone.classList.add('has-image');
-      submitBtn.disabled = false;
-      feedback.className = '';
-      feedback.style.display = 'none';
-
-      let d = null;
-      try { d = await readExifDate(file); } catch (_) {}
-      if (!d && file.lastModified) {
-        d = new Date(file.lastModified).toISOString().slice(0, 10);
-      }
-      if (d) dateInput.value = d;
-    });
-
-    submitBtn.addEventListener('click', async () => {
-      const file = fileInput.files[0];
-      if (!file) return;
-
-      submitBtn.disabled = true;
-      submitBtn.textContent = 'Uploading…';
-      feedback.className = '';
-
-      const form = new FormData();
-      form.append('image',   file);
-      form.append('caption', document.getElementById('caption').value);
-      form.append('date',    dateInput.value);
-      form.append('tags',    document.getElementById('tags').value);
-
-      try {
-        const res  = await fetch('/upload', { method: 'POST', body: form });
-        const text = (await res.text()).trim();
-        if (res.ok) {
-          feedback.className   = 'ok';
-          feedback.textContent = '✓ ' + text;
-          fileInput.value = '';
-          preview.style.display = 'none';
-          prompt.style.display  = 'flex';
-          dropZone.classList.remove('has-image');
-          document.getElementById('caption').value = '';
-          document.getElementById('tags').value = '';
-          submitBtn.disabled = true;
-        } else {
-          feedback.className   = 'err';
-          feedback.textContent = '✗ ' + text;
-          submitBtn.disabled   = false;
-        }
-      } catch (err) {
-        feedback.className   = 'err';
-        feedback.textContent = '✗ ' + err.message;
-        submitBtn.disabled   = false;
-      }
-
-      submitBtn.textContent = 'Upload photo';
-    });
   </script>
   <script src="/static/session.js"></script>
 </body>