diff --git a/src/MediaManager.html b/src/MediaManager.html
index d8122a3..9c35ba0 100644
--- a/src/MediaManager.html
+++ b/src/MediaManager.html
@@ -502,6 +502,26 @@
       opacity: 0.7;
       filter: grayscale(0.5);
     }
+
+    /* Selection Styles */
+    .media-item.selected {
+      border: 3px solid var(--primary);
+      box-shadow: 0 0 0 2px rgba(37, 99, 235, 0.2);
+    }
+
+    .icon-btn.active {
+      background-color: var(--primary);
+      color: white;
+    }
+
+    .btn-link {
+      background-color: var(--primary);
+      color: white;
+    }
+
+    .btn-link:hover {
+      background-color: var(--primary-hover);
+    }
   </style>
 </head>
 
@@ -527,10 +547,14 @@
 
     <div class="card" style="padding-bottom: 0;">
       <div class="header" style="margin-bottom:8px; display:flex; justify-content:space-between; align-items:center;">
-        <div style="display:flex; align-items:baseline; gap:12px;">
+        <div style="display:flex; align-items:center; gap:12px;">
           <h2 style="margin:0;">Gallery <span id="item-count"
               style="font-weight:400; color:var(--text-secondary); font-size:12px;">(0)</span></h2>
           <div id="quick-links" style="font-size:12px; display:flex; gap:8px;"></div>
+          <button id="btn-link-selected" onclick="controller.linkSelectedMedia()" class="btn btn-link"
+            style="display:none; width:auto; padding: 4px 12px; font-size:12px; height:28px;">
+            Link Selected
+          </button>
         </div>
         <div style="display: flex; gap: 8px;">
           <button id="toggle-log-btn" onclick="ui.toggleLog()"
@@ -679,8 +703,8 @@
   <div id="matching-modal" class="modal-overlay" style="z-index: 150;">
     <div class="card"
       style="width: 600px; max-width: 90%; text-align: center; padding: 24px; position: relative; background: #fff;">
-      <h3 style="margin-top:0;">Link Media?</h3>
-      <p style="color:var(--text-secondary); margin-bottom: 24px;">
+      <h3 id="match-modal-title" style="margin-top:0;">Link Media?</h3>
+      <p id="match-modal-text" style="color:var(--text-secondary); margin-bottom: 24px;">
         We found a matching file in Shopify. Should these be linked?
       </p>
 
@@ -741,6 +765,7 @@
       this.token = null;
       this.items = [];
       this.initialState = [];
+      this.selectedIds = new Set();
     }
 
     MediaState.prototype.setSku = function (info) {
@@ -754,10 +779,51 @@
     MediaState.prototype.setItems = function (items) {
       this.items = items || [];
       this.initialState = JSON.parse(JSON.stringify(this.items));
+      this.selectedIds.clear();
       ui.render(this.items);
       this.checkDirty();
     };
 
+                    MediaState.prototype.toggleSelection = function (id) {
+                      var item = this.items.find(function (i) { return i.id === id; });
+                      if (!item) return;
+
+                      var isSelected = this.selectedIds.has(id);
+
+                      if (isSelected) {
+                        this.selectedIds.delete(id);
+                      } else {
+                        // Enforce one-pair rule: Max one Drive, one Shopify
+                        var isDrive = (item.source === 'drive_only');
+                        var isShopify = (item.source === 'shopify_only');
+
+                        if (isDrive) {
+                          // Clear other Drive selections
+                          var _this = this;
+                          this.items.forEach(function (i) {
+                            if (i.source === 'drive_only' && _this.selectedIds.has(i.id)) {
+                              _this.selectedIds.delete(i.id);
+                            }
+                          });
+                        } else if (isShopify) {
+                          // Clear other Shopify selections
+                          var _this = this;
+                          this.items.forEach(function (i) {
+                            if (i.source === 'shopify_only' && _this.selectedIds.has(i.id)) {
+                              _this.selectedIds.delete(i.id);
+                            }
+                          });
+                        }
+                        this.selectedIds.add(id);
+                      }
+                      ui.render(this.items);
+                    };
+
+                    MediaState.prototype.clearSelection = function () {
+                      this.selectedIds.clear();
+                      ui.render(this.items);
+                    };
+
     MediaState.prototype.addItem = function (item) {
       this.items.push(item);
       ui.render(this.items);
@@ -982,6 +1048,20 @@
         banner.style.display = hasProcessing ? 'flex' : 'none';
       }
 
+      // Link Selected button logic
+      var btnLink = document.getElementById('btn-link-selected');
+      if (btnLink) {
+        var selectedItems = items.filter(function (i) { return state.selectedIds.has(i.id); });
+        var hasDrive = selectedItems.some(function (i) { return i.source === 'drive_only'; });
+        var hasShopify = selectedItems.some(function (i) { return i.source === 'shopify_only'; });
+
+        if (hasDrive && hasShopify) {
+          btnLink.style.display = 'block';
+        } else {
+          btnLink.style.display = 'none';
+        }
+      }
+
       if (items.length === 0) {
         this.grid.innerHTML = '<div class="empty-state">No media found. Upload something!</div>';
         return;
@@ -995,7 +1075,7 @@
       if (this.sortable) this.sortable.destroy();
       this.sortable = new Sortable(this.grid, {
         animation: 150,
-        filter: '.deleted-item',
+        filter: '.deleted-item', // Simplified filter
         ghostClass: 'sortable-ghost',
         dragClass: 'sortable-drag',
         onEnd: function () {
@@ -1084,7 +1164,8 @@
 
     UI.prototype.createCard = function (item, index) {
       var div = document.createElement('div');
-      div.className = 'media-item ' + (item._deleted ? 'deleted-item' : '');
+      var isSelected = state.selectedIds.has(item.id);
+      div.className = 'media-item ' + (item._deleted ? 'deleted-item' : '') + (isSelected ? ' selected' : '');
       div.dataset.id = item.id;
 
       // Processing Class
@@ -1092,6 +1173,8 @@
         div.className += ' processing-card';
       }
 
+
+
       div.onmouseenter = function () {
         var v = div.querySelector('video');
         if (v) v.play();
@@ -1103,9 +1186,9 @@
 
       var badge = '';
       if (!item._deleted) {
-        if (item.status === 'synced') badge = '<span class="badge" title="Synced" style="background:#dcfce7; color:#166534;">Synced</span>';
-        else if (item.status === 'drive_only') badge = '<span class="badge" title="Drive Only" style="background:#dbeafe; color:#1e40af;">Drive</span>';
-        else if (item.status === 'shopify_only') badge = '<span class="badge" title="Shopify Only" style="background:#fce7f3; color:#9d174d;">Shopify</span>';
+        if (item.source === 'synced') badge = '<span class="badge" title="Synced" style="background:#dcfce7; color:#166534;">Synced</span>';
+        else if (item.source === 'drive_only') badge = '<span class="badge" title="Drive Only" style="background:#dbeafe; color:#1e40af;">Drive</span>';
+        else if (item.source === 'shopify_only') badge = '<span class="badge" title="Shopify Only" style="background:#fce7f3; color:#9d174d;">Shopify</span>';
       } else {
         badge = '<span class="badge" style="background:#fee2e2; color:#991b1b;">Deleted</span>';
       }
@@ -1124,16 +1207,23 @@
       // content URL logic (Only relevant for Shopify where we have a direct public link)
       var contentUrl = item.contentUrl || "";
 
+      // Link selection button
+      var linkSelectionBtn = '';
+      if (!item._deleted && (item.source === 'drive_only' || item.source === 'shopify_only')) {
+        linkSelectionBtn = '<button class="icon-btn' + (isSelected ? ' active' : '') + '" onclick="event.stopPropagation(); state.toggleSelection(\'' + item.id + '\')" title="Select for linking">🔗</button>';
+      }
+
       var actionBtn = item._deleted
         ? '<button class="icon-btn" onclick="state.deleteItem(' + index + ')" title="Restore">↩️</button>'
         : '<button class="icon-btn btn-delete" onclick="state.deleteItem(' + index + ')" title="Delete">🗑️</button>';
 
-      div.innerHTML =
+      div.innerHTML +=
         badge +
         videoBadgeIcon +
         centerIcon +
         '<div class="media-overlay">' +
         '<button class="icon-btn btn-view" onclick="ui.openPreview(\'' + item.id + '\')" title="View">👁️</button>' +
+      linkSelectionBtn +
         actionBtn +
         '</div>';
 
@@ -1385,6 +1475,29 @@
           .getMediaManagerInitialState(sku, title);
       },
 
+      linkSelectedMedia() {
+        var selectedItems = state.items.filter(function (i) { return state.selectedIds.has(i.id); });
+        var driveItem = selectedItems.find(function (i) { return i.source === 'drive_only'; });
+        var shopifyItem = selectedItems.find(function (i) { return i.source === 'shopify_only'; });
+
+        if (!driveItem || !shopifyItem) {
+          alert("Please select exactly one Drive item and one Shopify item.");
+          return;
+        }
+
+        // Prepare a single match for the modal
+        this.matches = [{
+          drive: driveItem,
+          shopify: shopifyItem
+        }];
+        this.currentMatchIndex = 0;
+
+        // Custom text for manual link
+        document.getElementById('match-modal-title').innerText = "Confirm Manual Link";
+        document.getElementById('match-modal-text').innerText = "Are you sure you want to link these two items?";
+
+        this.startMatching();
+      },
 
       saveChanges() {
         ui.toggleSave(false);
@@ -1730,6 +1843,10 @@
           this.currentMatchIndex = 0;
           ui.logStatus('info', 'Found ' + newMatches.length + ' potential matches. Starting matching wizard...', 'info');
 
+          // Default text for automatic matching
+          document.getElementById('match-modal-title').innerText = "Link Media?";
+          document.getElementById('match-modal-text').innerText = "We found a matching file in Shopify. Should these be linked?";
+
           // Preload Images
           newMatches.forEach(function (m) {
             if (m.drive && m.drive.thumbnail) new Image().src = m.drive.thumbnail;