diff --git a/.claude/settings.local.json b/.claude/settings.local.json
index 6a368d3..524d740 100644
--- a/.claude/settings.local.json
+++ b/.claude/settings.local.json
@@ -3,7 +3,8 @@
     "allow": [
       "Bash(Get-ChildItem \"d:\\\\Projects\\\\LT_Janitorial_Quality_Control\\\\migrations\\\\versions\\\\\" -Name)",
       "PowerShell(Remove-Item \"d:\\\\Projects\\\\LT_Janitorial_Quality_Control\\\\app\\\\templates\\\\issues\\\\issues_view.html\" -Confirm:$false)",
-      "PowerShell(Remove-Item \"d:\\\\Projects\\\\LT_Janitorial_Quality_Control\\\\app\\\\templates\\\\issues\\\\issues_list.html\" -Confirm:$false)"
+      "PowerShell(Remove-Item \"d:\\\\Projects\\\\LT_Janitorial_Quality_Control\\\\app\\\\templates\\\\issues\\\\issues_list.html\" -Confirm:$false)",
+      "Bash(Get-ChildItem -Path \"d:\\\\Projects\\\\LT_Janitorial_Quality_Control\\\\app\\\\templates\\\\inspections\\\\\" -Name)"
     ]
   }
 }
diff --git a/app/routes/inspections.py b/app/routes/inspections.py
index e346c88..fe8d047 100644
--- a/app/routes/inspections.py
+++ b/app/routes/inspections.py
@@ -499,6 +499,33 @@ def save_draft_ajax(inspection_id):
     return jsonify({'ok': True})
 
 
+# ── AJAX: upload a single inspection photo ────────────────────────────────────
+
+@bp.route('/<int:inspection_id>/upload-photo', methods=['POST'])
+@login_required
+def upload_photo_ajax(inspection_id):
+    inspection = db.session.get(Inspection, inspection_id)
+    if inspection is None:
+        return jsonify({'ok': False, 'error': 'Not found'}), 404
+
+    if current_user.role == 'inspector' and inspection.inspector_id != current_user.id:
+        return jsonify({'ok': False, 'error': 'Access denied'}), 403
+
+    if inspection.status == 'completed':
+        return jsonify({'ok': False, 'error': 'Inspection already completed'}), 400
+
+    file_obj = request.files.get('photo')
+    path = _save_photo(file_obj, subfolder='inspection_photos')
+    if not path:
+        return jsonify({'ok': False, 'error': 'Invalid file or unsupported format'}), 400
+
+    current_app.logger.info(
+        'INSPECTION PHOTO UPLOADED (AJAX) | inspection_id=%s | path=%s | by=%s',
+        inspection_id, path, current_user.username
+    )
+    return jsonify({'ok': True, 'path': path})
+
+
 # ── View ──────────────────────────────────────────────────────────────────────
 
 @bp.route('/<int:inspection_id>')
diff --git a/app/templates/inspections/execute.html b/app/templates/inspections/execute.html
index 93349db..958fe51 100644
--- a/app/templates/inspections/execute.html
+++ b/app/templates/inspections/execute.html
@@ -413,13 +413,17 @@
         {% elif field.type == 'image' %}
           <label class="field-lbl">{{ field.label }}{% if field.required %}<span class="required-mark"> *</span>{% endif %}</label>
           {# Single <label> element: tap anywhere to pick a photo.
-             Filename + remove button appear on the right when a file is chosen. #}
+             Filename + remove button appear on the right when a file is chosen.
+             The hidden server_path input stores the AJAX-uploaded path so it is
+             included in the Flag-Issue draft save (file inputs can't be serialised). #}
           <label class="upload-zone" for="field_{{ fid }}" id="zone_{{ fid }}">
             <input type="file" name="field_{{ fid }}" id="field_{{ fid }}" accept="image/*"
-                   onchange="showFileName(this)">
+                   onchange="uploadPhotoField(this)"
+                   data-upload-url="{{ url_for('inspections.upload_photo_ajax', inspection_id=inspection.id) }}">
+            <input type="hidden" id="field_{{ fid }}_server_path" value="{{ saved or '' }}">
             <div class="upload-main">
-              <i class="bi bi-cloud-upload"></i>
-              <span class="upload-prompt">Tap to take / choose photo</span>
+              <i class="bi bi-cloud-upload" id="icon_{{ fid }}"></i>
+              <span class="upload-prompt" id="prompt_{{ fid }}">Tap to take / choose photo</span>
             </div>
             <div class="upload-chosen{% if saved %} has-file{% endif %}" id="chosen_{{ fid }}">
               <span class="upload-fname" id="fname_{{ fid }}">{% if saved %}{{ saved.split('/')[-1] }}{% endif %}</span>
@@ -560,33 +564,79 @@ function setRating(btn) {
   });
 }
 
-// ── File upload: show filename + reveal the chosen panel ────────────────────
-function showFileName(input) {
-  const fid    = input.id.replace('field_', '');
-  const fname  = document.getElementById('fname_'  + fid);
-  const chosen = document.getElementById('chosen_' + fid);
+// ── Photo upload on select: immediately uploads to server ────────────────────
+// Stores the server path in a hidden field so the Flag-Issue AJAX draft save
+// can include it — file inputs cannot be JSON-serialised or sent in a JSON body.
+async function uploadPhotoField(input) {
+  const fid        = input.id.replace('field_', '');
+  const fname      = document.getElementById('fname_'   + fid);
+  const chosen     = document.getElementById('chosen_'  + fid);
+  const pathHidden = document.getElementById('field_'   + fid + '_server_path');
+  const iconEl     = document.getElementById('icon_'    + fid);
+  const promptEl   = document.getElementById('prompt_'  + fid);
 
-  if (input.files && input.files.length > 0) {
-    if (fname)  fname.textContent = input.files[0].name;
-    if (chosen) chosen.classList.add('has-file');
+  if (!input.files || !input.files.length) return;
+  const file = input.files[0];
+
+  // Show the filename chip immediately (optimistic UI)
+  if (fname)  fname.textContent = file.name;
+  if (chosen) chosen.classList.add('has-file');
+
+  // Show uploading state
+  if (iconEl)   iconEl.className     = 'bi bi-hourglass-split';
+  if (promptEl) promptEl.textContent = 'Uploading…';
+
+  try {
+    const uploadUrl = input.dataset.uploadUrl;
+    const csrfToken = document.querySelector('input[name="csrf_token"]').value;
+
+    const compressed = await compressImageFile(file);
+    const fd = new FormData();
+    fd.append('photo', compressed, file.name);
+    fd.append('csrf_token', csrfToken);
+
+    const res  = await fetch(uploadUrl, { method: 'POST', body: fd });
+    const json = await res.json();
+
+    if (json.ok && json.path) {
+      if (pathHidden) pathHidden.value     = json.path;
+      if (iconEl)     iconEl.className     = 'bi bi-check-circle-fill';
+      if (promptEl)   promptEl.textContent = 'Photo saved';
+    } else {
+      // Upload failed — file is still in the input, will be sent on full form submit
+      if (iconEl)     iconEl.className     = 'bi bi-cloud-upload';
+      if (promptEl)   promptEl.textContent = 'Tap to take / choose photo';
+      console.error('Photo AJAX upload failed:', json.error);
+    }
+  } catch (err) {
+    // Network error — same fallback: file stays in input for final form submit
+    if (iconEl)     iconEl.className     = 'bi bi-cloud-upload';
+    if (promptEl)   promptEl.textContent = 'Tap to take / choose photo';
+    console.error('Photo upload error:', err);
   }
 }
 
 // ── Clear a photo upload field ────────────────────────────────────────────────
 // iOS: input.files is read-only — replace the element to truly reset it.
 function clearUpload(fid) {
-  const input  = document.getElementById('field_'  + fid);
-  const fname  = document.getElementById('fname_'  + fid);
-  const chosen = document.getElementById('chosen_' + fid);
+  const input      = document.getElementById('field_'  + fid);
+  const fname      = document.getElementById('fname_'  + fid);
+  const chosen     = document.getElementById('chosen_' + fid);
+  const pathHidden = document.getElementById('field_'  + fid + '_server_path');
+  const iconEl     = document.getElementById('icon_'   + fid);
+  const promptEl   = document.getElementById('prompt_' + fid);
 
   if (input) {
     const newInput = input.cloneNode(false);
     newInput.value = '';
-    newInput.addEventListener('change', function() { showFileName(this); });
+    newInput.addEventListener('change', function() { uploadPhotoField(this); });
     input.parentNode.replaceChild(newInput, input);
   }
-  if (fname)  fname.textContent = '';
-  if (chosen) chosen.classList.remove('has-file');
+  if (fname)      fname.textContent        = '';
+  if (chosen)     chosen.classList.remove('has-file');
+  if (pathHidden) pathHidden.value         = '';
+  if (iconEl)     iconEl.className         = 'bi bi-cloud-upload';
+  if (promptEl)   promptEl.textContent     = 'Tap to take / choose photo';
 }
 
 // ── Signature pads ────────────────────────────────────────────────────────────
@@ -800,6 +850,14 @@ document.getElementById('inspectionForm').addEventListener('submit', async funct
       responses[el.name.replace('field_', '')] = el.value;
     });
 
+    // Include server paths for image fields that were already AJAX-uploaded.
+    // These are stored in no-name hidden inputs (id="field_<fid>_server_path")
+    // so they don't interfere with the multipart form POST.
+    form.querySelectorAll('input[id$="_server_path"]').forEach(function(pathEl) {
+      const m = pathEl.id.match(/^field_(.+)_server_path$/);
+      if (m && pathEl.value) responses[m[1]] = pathEl.value;
+    });
+
     btn.disabled = true;
     btn.innerHTML = '<span class="spinner-border spinner-border-sm me-1"></span> Saving…';