diff --git a/frontend/src/DesktopWorkspace.css b/frontend/src/DesktopWorkspace.css
index efb4955..dd5a0ec 100644
--- a/frontend/src/DesktopWorkspace.css
+++ b/frontend/src/DesktopWorkspace.css
@@ -1,4 +1,4 @@
-/* Skeuomorphic workspace styles */
+/* Desktop workspace styles */
 .skeuo-main {
   flex: 1;
   display: flex;
diff --git a/frontend/src/DesktopWorkspace.jsx b/frontend/src/DesktopWorkspace.jsx
index 4887a39..6bd9719 100644
--- a/frontend/src/DesktopWorkspace.jsx
+++ b/frontend/src/DesktopWorkspace.jsx
@@ -32,7 +32,6 @@ const resolveSizeKey = (doc) =>
 
 const CARD_MIN = 240;
 const CARD_MAX = 340;
-const EMPTY_CARD_ASPECT = 1.4;
 const TAG_REMOVE_DISTANCE = 160;
 
 const DEBUG_DRAG = false;
@@ -83,7 +82,7 @@ const resolveTagKey = (tag) => {
   return key != null ? String(key) : null;
 };
 
-const SkeuoPreviewCard = ({
+const DesktopPreviewCard = ({
   doc,
   title,
   ensureAssetUrl,
@@ -359,6 +358,87 @@ const cleanupPreview = (previewNode) => {
   }
 };
 
+const usePreviewMetadata = (documents, getDocumentAsset, ensureAssetUrl) => {
+  const [metadataMap, setMetadataMap] = useState(() => new Map());
+
+  useEffect(() => {
+    let cancelled = false;
+    const docs = Array.isArray(documents) ? documents : [];
+    if (!docs.length) {
+      setMetadataMap(new Map());
+      return () => {
+        cancelled = true;
+      };
+    }
+
+    const fetchMetadataForDoc = async (doc) => {
+      if (!doc?.id) {
+        return null;
+      }
+
+      const docId = String(doc.id);
+      const resolveAsset = (type) => (typeof getDocumentAsset === 'function' ? getDocumentAsset(doc, type) : null);
+
+      let asset = resolveAsset('preview') || resolveAsset('thumbnail');
+      let view = createAssetView(asset);
+      let metadata = view.getPrimaryMetadata();
+
+      const hasDimensions = (meta) =>
+        Number.isFinite(Number(meta?.width)) && Number.isFinite(Number(meta?.height)) &&
+        Number(meta.width) > 0 && Number(meta.height) > 0;
+
+      if (!hasDimensions(metadata) && ensureAssetUrl && docId && asset?.id) {
+        try {
+          const ensured = await ensureAssetUrl(doc.id, asset, { start: 1, limit: 1 });
+          if (ensured) {
+            asset = ensured;
+            view = createAssetView(asset);
+            metadata = view.getPrimaryMetadata();
+          }
+        } catch (
+          // eslint-disable-next-line no-empty
+          error
+        ) {}
+      }
+
+      if (!hasDimensions(metadata)) {
+        return null;
+      }
+
+      const width = Number(metadata.width);
+      const height = Number(metadata.height);
+      if (!Number.isFinite(width) || !Number.isFinite(height)) {
+        return null;
+      }
+
+      return [docId, { width, height }];
+    };
+
+    Promise.all(docs.map((doc) => fetchMetadataForDoc(doc)))
+      .then((entries) => {
+        if (cancelled) return;
+        const next = new Map();
+        entries.forEach((entry) => {
+          if (entry) {
+            next.set(entry[0], entry[1]);
+          }
+        });
+        setMetadataMap(next);
+      })
+      .catch(() => {
+        if (!cancelled) {
+          setMetadataMap(new Map());
+        }
+      });
+
+    return () => {
+      cancelled = true;
+    };
+  }, [documents, getDocumentAsset, ensureAssetUrl]);
+
+  return metadataMap;
+};
+
 const seededRandom = (input) => {
   const text = String(input);
   let hash = 2166136261;
@@ -379,50 +459,66 @@ const randomRangeFromSeed = (seedKey, min, max) => {
 const buildKey = (docId, suffix) => `${docId}::${suffix}`;
 
 const clampCardDimensions = (width, height) => {
-  let w = Number(width);
-  let h = Number(height);
+  const w = Number(width);
+  const h = Number(height);
 
   if (!Number.isFinite(w) || !Number.isFinite(h) || w <= 0 || h <= 0) {
     return null;
   }
 
-  const scaleToFit = (maxWidth, maxHeight, currentWidth, currentHeight) => {
-    if (currentWidth <= maxWidth && currentHeight <= maxHeight) {
-      return 1;
+  const low = Math.max(CARD_MIN / w, CARD_MIN / h);
+  const high = Math.min(CARD_MAX / w, CARD_MAX / h);
+
+  const candidates = [];
+  const addCandidate = (scale) => {
+    if (Number.isFinite(scale) && scale > 0) {
+      candidates.push(scale);
     }
-    return Math.min(maxWidth / currentWidth, maxHeight / currentHeight);
   };
 
-  const scaleToFill = (minWidth, minHeight, currentWidth, currentHeight) => {
-    if (currentWidth >= minWidth && currentHeight >= minHeight) {
-      return 1;
+  addCandidate(1);
+  addCandidate(low);
+  addCandidate(high);
+
+  const best = candidates.reduce((acc, scale) => {
+    const scaledWidth = w * scale;
+    const scaledHeight = h * scale;
+    const violation = Math.max(
+      Math.max(CARD_MIN - scaledWidth, 0),
+      Math.max(scaledWidth - CARD_MAX, 0),
+      Math.max(CARD_MIN - scaledHeight, 0),
+      Math.max(scaledHeight - CARD_MAX, 0),
+    );
+    const deviation = Math.abs(scale - 1);
+    if (!acc || violation < acc.violation || (violation === acc.violation && deviation < acc.deviation)) {
+      return { scale, violation, deviation };
     }
-    return Math.max(minWidth / currentWidth, minHeight / currentHeight);
-  };
-
-  // Step 1: scale down so both dimensions fit within the maximum bounds.
-  const downScale = scaleToFit(CARD_MAX, CARD_MAX, w, h);
-  w *= downScale;
-  h *= downScale;
-
-  // Step 2: if the card is too small, scale up (preserving ratio).
-  const upScale = scaleToFill(CARD_MIN, CARD_MIN, w, h);
-  w *= upScale;
-  h *= upScale;
-
-  // Step 3: Re-apply upper bounds if the scale-up pushed us over.
-  if (w > CARD_MAX || h > CARD_MAX) {
-    const adjust = scaleToFit(CARD_MAX, CARD_MAX, w, h);
-    w *= adjust;
-    h *= adjust;
-  }
+    return acc;
+  }, null);
 
+  const scale = best ? best.scale : 1;
   return {
-    width: w,
-    height: h,
+    width: Math.round(w * scale),
+    height: Math.round(h * scale),
   };
 };
 
+const computeFallbackCardSize = (docId) => {
+  const baseSeed = seededRandom(`${docId}:fallback-size`);
+  const aspectSeed = seededRandom(`${docId}:fallback-aspect`);
+
+  const width = CARD_MIN + baseSeed * (CARD_MAX - CARD_MIN);
+  const isPortrait = aspectSeed < 0.5;
+  const normalizedSeed = isPortrait ? aspectSeed / 0.5 : (aspectSeed - 0.5) / 0.5;
+  const aspectRange = 0.75; // keeps generated ratio pleasant but varied
+  const aspect = isPortrait
+    ? 1 + normalizedSeed * aspectRange
+    : 1 / (1 + normalizedSeed * aspectRange);
+  const height = width * aspect;
+
+  return clampCardDimensions(width, height);
+};
+
 const DesktopWorkspace = ({
   documents = [],
   searchResults = null,
@@ -459,6 +555,7 @@ const DesktopWorkspace = ({
   const docSizeMapRef = useRef(new Map());
   const documentLookupRef = useRef(new Map());
   const removalCursorActiveRef = useRef(false);
+  const previewMetadata = usePreviewMetadata(items, getDocumentAsset, ensureAssetUrl);
   const documentLookup = useMemo(() => {
     const map = new Map();
     items.forEach((doc) => {
@@ -473,7 +570,26 @@ const DesktopWorkspace = ({
   useEffect(() => {
     documentLookupRef.current = documentLookup;
   }, [documentLookup]);
-  const applySnapshotDimensions = useCallback(() => {}, []);
+
+  const applySnapshotDimensions = useCallback((docKey, snapshot) => {
+    const width = Number(snapshot?.width);
+    const height = Number(snapshot?.height);
+    if (!Number.isFinite(width) || !Number.isFinite(height) || width <= 0 || height <= 0) {
+      return;
+    }
+    const normalized = clampCardDimensions(width, height);
+    if (!normalized) {
+      return;
+    }
+    const existing = docSizeMapRef.current.get(docKey);
+    if (existing && existing.width === normalized.width && existing.height === normalized.height) {
+      return;
+    }
+    const next = new Map(docSizeMapRef.current);
+    next.set(docKey, { ...normalized, source: 'snapshot' });
+    docSizeMapRef.current = next;
+    setDocSizeVersion((value) => value + 1);
+  }, []);
   const handleNavigatorSnapshot = useCallback(
     (docId, snapshot) => {
       const docKey = docId != null ? String(docId) : null;
@@ -530,29 +646,14 @@ const DesktopWorkspace = ({
     return set;
   }, [activeTagIds]);
 
-  const resolvePreviewAsset = useCallback(
-    (doc) => {
-      if (!doc) return null;
-      return getDocumentAsset(doc, 'thumbnail');
-    },
-    [getDocumentAsset],
-  );
-
   const resolvePreviewDimensions = useCallback(
     (doc) => {
-      if (!doc) return null;
-
-      const asset = resolvePreviewAsset(doc);
-      const view = createAssetView(asset);
-      const metadata = view.getPrimaryMetadata() || {};
-      const width = metadata?.width;
-      const height = metadata?.height;
-      if (typeof width === 'number' && typeof height === 'number') {
-        return { width, height };
+      if (!doc?.id) {
+        return null;
       }
-      return null;
+      return previewMetadata.get(String(doc.id)) || null;
     },
-    [resolvePreviewAsset],
+    [previewMetadata],
   );
 
   useEffect(() => {
@@ -661,37 +762,60 @@ const DesktopWorkspace = ({
   }, [updateRemovalCursor]);
 
   const ensureDocumentSize = useCallback((doc) => {
-    const key = resolveSizeKey(doc);
-    const cache = docSizeMapRef.current.get(key);
-    if (cache) {
-      return cache;
+    if (!doc?.id) {
+      return null;
     }
-    const intrinsic = resolvePreviewDimensions(doc);
-    let normalized = null;
-    if (intrinsic?.width && intrinsic?.height) {
-      normalized = clampCardDimensions(intrinsic.width, intrinsic.height);
-    }
-
-    if (!normalized) {
-      const seed = seededRandom(`${key}:size`);
-      let width = CARD_MIN + seed * (Math.min(CARD_MAX, CARD_MAX / EMPTY_CARD_ASPECT) - CARD_MIN);
-      width = clamp(width, CARD_MIN, Math.min(CARD_MAX, CARD_MAX / EMPTY_CARD_ASPECT));
-      const height = width * EMPTY_CARD_ASPECT;
-      normalized = clampCardDimensions(width, height);
-    }
-
-    if (!normalized) {
-      normalized = { width: CARD_MIN, height: CARD_MIN };
-    }
-
-    docSizeMapRef.current.set(key, normalized);
-    return normalized;
-  }, [resolvePreviewDimensions]);
+    return docSizeMapRef.current.get(String(doc.id)) || null;
+  }, []);
 
   useEffect(() => {
-    docSizeMapRef.current = new Map();
-    setDocSizeVersion((value) => value + 1);
-  }, [items]);
+    const current = docSizeMapRef.current;
+    const next = new Map(current);
+    const itemKeys = new Set(items.filter((doc) => doc?.id != null).map((doc) => String(doc.id)));
+    let changed = false;
+
+    items.forEach((doc) => {
+      if (!doc?.id) {
+        return;
+      }
+      const key = String(doc.id);
+      const existing = next.get(key) || null;
+      const meta = previewMetadata.get(key);
+      if (meta) {
+        const normalized = clampCardDimensions(meta.width, meta.height);
+        if (normalized) {
+          if (existing?.source === 'snapshot') {
+            return;
+          }
+          if (!existing || existing.width !== normalized.width || existing.height !== normalized.height || existing.source !== 'metadata') {
+            next.set(key, { ...normalized, source: 'metadata' });
+            changed = true;
+          }
+          return;
+        }
+      }
+
+      if (!existing) {
+        const fallback = computeFallbackCardSize(key);
+        if (fallback) {
+          next.set(key, { ...fallback, source: 'fallback' });
+          changed = true;
+        }
+      }
+    });
+
+    current.forEach((_, key) => {
+      if (!itemKeys.has(key)) {
+        next.delete(key);
+        changed = true;
+      }
+    });
+
+    if (changed) {
+      docSizeMapRef.current = next;
+      setDocSizeVersion((value) => value + 1);
+    }
+  }, [items, previewMetadata]);
 
   const overlayDisplay = useMemo(() => {
     if (!overlayDocId) {
@@ -867,7 +991,11 @@ const recalcVisibleDocIds = useCallback(() => {
       if (!doc) {
         return;
       }
-      const { width: cardWidth, height: cardHeight } = ensureDocumentSize(doc);
+      const sizeInfo = ensureDocumentSize(doc);
+      if (!sizeInfo) {
+        return;
+      }
+      const { width: cardWidth, height: cardHeight } = sizeInfo;
       const rotationDeg = Number(entry?.rotation) || 0;
       const rotationRad = (rotationDeg * Math.PI) / 180;
       const cosRot = Math.cos(rotationRad);
@@ -1015,6 +1143,11 @@ const syncLayoutSnapshot = useCallback(() => {
       return;
     }
 
+    const missingSizes = items.some((doc) => !ensureDocumentSize(doc));
+    if (missingSizes) {
+      return;
+    }
+
     const previous = layoutRef.current;
     const next = new Map();
     let maxZ = zCounterRef.current;
@@ -1023,7 +1156,11 @@ const syncLayoutSnapshot = useCallback(() => {
     const docsNeedingLayout = [];
 
     items.forEach((doc) => {
-      const { width: docWidth, height: docHeight } = ensureDocumentSize(doc);
+      const sizeInfo = ensureDocumentSize(doc);
+      if (!sizeInfo) {
+        return;
+      }
+      const { width: docWidth, height: docHeight } = sizeInfo;
       const halfWidth = docWidth / 2;
       const halfHeight = docHeight / 2;
 
@@ -1141,7 +1278,11 @@ const syncLayoutSnapshot = useCallback(() => {
       if (!originTransform) {
         const entry = layoutRef.current.get(docId) || null;
         const doc = documentLookup.get(docKey) || null;
-        const { width: cardWidth, height: cardHeight } = ensureDocumentSize(doc);
+        const sizeInfo = ensureDocumentSize(doc);
+        if (!sizeInfo) {
+          return;
+        }
+        const { width: cardWidth, height: cardHeight } = sizeInfo;
         const { baseWidth, baseHeight, baseScale } = resolveBaseMetrics(doc, cardWidth, cardHeight);
         const effectiveWidth = baseWidth * baseScale;
         const effectiveHeight = baseHeight * baseScale;
@@ -1620,6 +1761,7 @@ const syncLayoutSnapshot = useCallback(() => {
       handleCanvasDragLeave,
       handleCanvasDrop,
       layoutSnapshot,
+      docSizeVersion,
       visibleDocIds,
       draggingId,
       tagDropTargetId,
@@ -1669,6 +1811,7 @@ const syncLayoutSnapshot = useCallback(() => {
       items,
       layoutRef,
       layoutSnapshot,
+      docSizeVersion,
       onDocumentOpen,
       openOverlayForDoc,
       overlayDisplay,
@@ -1726,11 +1869,17 @@ const DesktopWorkspaceView = () => {
     closeOverlay,
     overlayOriginRect,
     overlayOriginTransform,
+    docSizeVersion,
   } = useDesktopContext();
 
   const { handlePointerDown, handlePointerMove, handlePointerUp, handlePointerCancel } =
     useDocumentDrag();
 
+  const allSizesReady = useMemo(
+    () => items.every((doc) => ensureDocumentSize(doc)),
+    [items, ensureDocumentSize, docSizeVersion],
+  );
+
   return (
     <>
       <div className="skeuo-shell">
@@ -1741,13 +1890,20 @@ const DesktopWorkspaceView = () => {
           onDragLeave={handleCanvasDragLeave}
           onDrop={handleCanvasDrop}
         >
-          {items.length === 0 ? (
+          {!allSizesReady ? (
+            <div className="skeuo-empty">
+              <p>Loading previews…</p>
+            </div>
+          ) : items.length === 0 ? (
             <div className="skeuo-empty">
               <p>No documents to show here yet. Drop files to make this space come alive.</p>
             </div>
           ) : (
             items.map((doc) => {
               const sizeInfo = ensureDocumentSize(doc);
+              if (!sizeInfo) {
+                return null;
+              }
               const { width: cardWidth, height: cardHeight } = sizeInfo;
               const layout = layoutSnapshot.get(doc.id) ?? layoutRef.current.get(doc.id);
               if (
@@ -1824,7 +1980,7 @@ const DesktopWorkspaceView = () => {
                   }}
                 >
                   <div className="skeuo-item__body">
-                    <SkeuoPreviewCard
+                    <DesktopPreviewCard
                       doc={doc}
                       title={title}
                       ensureAssetUrl={ensureAssetUrl}
diff --git a/frontend/src/desktop/useDocumentDrag.js b/frontend/src/desktop/useDocumentDrag.js
index 7f58792..c310ce5 100644
--- a/frontend/src/desktop/useDocumentDrag.js
+++ b/frontend/src/desktop/useDocumentDrag.js
@@ -75,7 +75,6 @@ const useDocumentDrag = () => {
         layoutRef.current.set(docId, { ...entry, centerX, centerY });
       }
 
-      bringToFront(docId);
       const capturedTarget = event.currentTarget instanceof HTMLElement ? event.currentTarget : null;
       if (capturedTarget && typeof capturedTarget.setPointerCapture === 'function') {
         try {
@@ -100,6 +99,7 @@ const useDocumentDrag = () => {
         dragScale: 1,
         baseScale: normalizedBaseScale,
         capturedTarget,
+        raised: false,
       };
       setDraggingId(docId);
     },
@@ -175,6 +175,11 @@ const useDocumentDrag = () => {
         return;
       }
 
+      if (!state.raised) {
+        bringToFront(state.docId);
+        state.raised = true;
+      }
+
       const updated = { ...entry, centerX: clampedCenterX, centerY: clampedCenterY };
       layoutRef.current.set(state.docId, updated);
 
@@ -210,24 +215,26 @@ const useDocumentDrag = () => {
     (event) => {
       const state = dragStateRef.current;
       if (state && state.pointerId === event.pointerId) {
-        const moved = Boolean(state.moved);
-        const docId = state.docId;
-        const shouldOpen = !moved && event.detail >= 2;
-        finishDrag(event.pointerId);
-        if (shouldOpen) {
-          const originInfo = {
-            rotation: state.rotation || 0,
-            scale: state.baseScale || 1,
-            width: state.width,
-            height: state.height,
-          };
-          openOverlayForDoc(docId, originInfo);
+        if (state.moved) {
+          finishDrag(event.pointerId);
+          return;
         }
+
+        const docId = state.docId;
+        bringToFront(docId);
+        const originInfo = {
+          rotation: state.rotation || 0,
+          scale: state.baseScale || 1,
+          width: state.width,
+          height: state.height,
+        };
+        finishDrag(event.pointerId);
+        openOverlayForDoc(docId, originInfo);
         return;
       }
       finishDrag(event.pointerId);
     },
-    [finishDrag, openOverlayForDoc],
+    [bringToFront, finishDrag, openOverlayForDoc],
   );
 
   const handlePointerCancel = useCallback(