diff --git a/frontend/src/desktop/components/DesktopWorkspace.tsx b/frontend/src/desktop/components/DesktopWorkspace.tsx
index 9dc4994..3b6ef9a 100644
--- a/frontend/src/desktop/components/DesktopWorkspace.tsx
+++ b/frontend/src/desktop/components/DesktopWorkspace.tsx
@@ -110,22 +110,71 @@ const DesktopWorkspaceContent: React.FC<DesktopWorkspaceProps> = ({
     }
   }, [layoutStore, tenantId, viewId]);
 
-  // Only set layout ready when both container has size AND layout is loaded
-  useEffect(() => {
-    setIsLayoutReady(hasContainerSize && isLayoutLoaded);
-  }, [hasContainerSize, isLayoutLoaded]);
+  const metadataMap = usePreviewMetadata(items, getDocumentAsset, ensureAssetUrl);
 
-  // Sync LayoutStore items with current entries to remove stale items
+  const ensureDocumentSize = useCallback((doc: Document): DocumentSizeInfo => {
+    if (doc.id) {
+      const meta = metadataMap.get(String(doc.id));
+      if (meta && meta.width && meta.height)
+        return { width: meta.width, height: meta.height, source: 'metadata' };
+    }
+
+    return computeFallbackCardSize(doc, defaultCardSize);
+  }, [metadataMap, defaultCardSize]);
+
+  // Synchronize LayoutStore with current items (Initialization & Cleanup)
   useEffect(() => {
+    if (!hasContainerSize || !isLayoutLoaded) return;
+
+    // Cleanup Stale Items
     const currentIds = new Set(items.map((doc, index) => doc.id ? String(doc.id) : `temp-${index}`));
-
-    // Identify and remove items that are no longer present
     for (const id of layoutStore.items.keys()) {
       if (!currentIds.has(id)) {
         layoutStore.unregister(id);
       }
     }
-  }, [items, layoutStore]);
+
+    // Initialize / Update Items (Saved first, then others)
+    const itemsWithSavedLayout: Document[] = [];
+    const itemsWithoutSavedLayout: Document[] = [];
+
+    items.forEach(doc => {
+      // If already initialized in store, we don't strictly need to prioritize it for collision, 
+      // but keeping the order ensures consistent behavior on re-runs.
+      // However, usually we only care about *new* items for collision logic.
+      if (doc.id && layoutStore.hasSavedLayout(String(doc.id))) {
+        itemsWithSavedLayout.push(doc);
+      } else {
+        itemsWithoutSavedLayout.push(doc);
+      }
+    });
+
+    const initializeDoc = (doc: Document) => {
+      const size = ensureDocumentSize(doc);
+      const metadata = doc.current_version?.metadata as { page_count?: number } | undefined;
+      const pageCount = metadata?.page_count ?? 1;
+
+      layoutStore.initialize(doc.id, null, {
+        width: size.width,
+        height: size.height,
+        pageCount,
+        maxSize: defaultCardSize
+      });
+    };
+
+    itemsWithSavedLayout.forEach(initializeDoc);
+    itemsWithoutSavedLayout.forEach(initializeDoc);
+
+    // Save newly placed items
+    if (itemsWithoutSavedLayout.length > 0) {
+      void layoutStore.saveLayout();
+    }
+
+    // Enforce constraints
+    layoutStore.relayout();
+
+    setIsLayoutReady(true);
+  }, [hasContainerSize, isLayoutLoaded, items, layoutStore, ensureDocumentSize, defaultCardSize]);
 
   // Selection Context
   const {
@@ -155,18 +204,6 @@ const DesktopWorkspaceContent: React.FC<DesktopWorkspaceProps> = ({
     clearSelection ? clearSelection() : handleSelectionChange([]);
   }, [clearSelection, handleSelectionChange]);
 
-  const metadataMap = usePreviewMetadata(items, getDocumentAsset, ensureAssetUrl);
-
-  const ensureDocumentSize = useCallback((doc: Document): DocumentSizeInfo => {
-    if (doc.id) {
-      const meta = metadataMap.get(String(doc.id));
-      if (meta && meta.width && meta.height)
-        return { width: meta.width, height: meta.height, source: 'metadata' };
-    }
-
-    return computeFallbackCardSize(doc, defaultCardSize);
-  }, [metadataMap, defaultCardSize]);
-
   // Sync LayoutStore to layoutRef
   useEffect(() => {
     const sync = () => {
@@ -351,18 +388,12 @@ const DesktopWorkspaceContent: React.FC<DesktopWorkspaceProps> = ({
           {isLayoutReady && items.map((doc, index) => {
             const docId = doc.id ? String(doc.id) : `temp-${index}`;
             const isSelected = selectedDocumentIds.includes(docId);
-            const size = ensureDocumentSize(doc);
 
-            // Extract page count
-            const metadata = doc.current_version?.metadata as { page_count?: number } | undefined;
-            const pageCount = metadata?.page_count ?? 1;
+            const layoutCard = layoutStore.items.get(docId);
 
-            const layoutCard = layoutStore.initialize(docId, null, {
-              width: size.width,
-              height: size.height,
-              pageCount,
-              maxSize: defaultCardSize
-            });
+            if (!layoutCard) {
+              return null;
+            }
 
             return (
               <DesktopDocumentCard
diff --git a/frontend/src/desktop/logic/LayoutSystem.ts b/frontend/src/desktop/logic/LayoutSystem.ts
index 16d56cd..58eb399 100644
--- a/frontend/src/desktop/logic/LayoutSystem.ts
+++ b/frontend/src/desktop/logic/LayoutSystem.ts
@@ -538,6 +538,10 @@ export class LayoutStore {
         this.relayout();
     }
 
+    hasSavedLayout(id: string): boolean {
+        return this.savedLayouts.has(id);
+    }
+
     async saveLayout() {
         if (!this.tenantId || !this.viewId) return;