diff --git a/Rosetta/Core/Layout/MessageCellLayout.swift b/Rosetta/Core/Layout/MessageCellLayout.swift
index a4d6d8b..7856a87 100644
--- a/Rosetta/Core/Layout/MessageCellLayout.swift
+++ b/Rosetta/Core/Layout/MessageCellLayout.swift
@@ -211,9 +211,21 @@ extension MessageCellLayout {
         // Tiny floor just to prevent zero-width collapse.
         // Telegram does NOT force a large minW — short messages get tight bubbles.
         let minW: CGFloat = 40
+        let mediaWidthFraction: CGFloat
+        let mediaAbsoluteCap: CGFloat
+        if config.imageCount == 1 {
+            mediaWidthFraction = 0.64
+            mediaAbsoluteCap = 288
+        } else if config.imageCount == 2 {
+            mediaWidthFraction = 0.67
+            mediaAbsoluteCap = 300
+        } else {
+            mediaWidthFraction = 0.7
+            mediaAbsoluteCap = 312
+        }
         let mediaBubbleMaxWidth = min(
             effectiveMaxBubbleWidth,
-            max(220, UIScreen.main.bounds.width * 0.78)
+            min(mediaAbsoluteCap, max(200, UIScreen.main.bounds.width * mediaWidthFraction))
         )
 
         var bubbleW: CGFloat
@@ -390,14 +402,14 @@ extension MessageCellLayout {
     /// Photo collage height — same formulas as C++ MessageLayout & PhotoCollageView.swift.
     private static func collageHeight(count: Int, width: CGFloat) -> CGFloat {
         guard count > 0 else { return 0 }
-        if count == 1 { return min(width * 0.75, 320) }
+        if count == 1 { return max(180, min(width * 0.93, 340)) }
         if count == 2 {
             let cellW = (width - 2) / 2
-            return min(cellW * 1.2, 320)
+            return min(cellW * 1.28, 330)
         }
         if count == 3 {
             let leftW = width * 0.66
-            return min(leftW * 1.1, 320)
+            return min(leftW * 1.16, 330)
         }
         if count == 4 {
             let cellW = (width - 2) / 2
diff --git a/Rosetta/Features/Chats/ChatDetail/ChatDetailView.swift b/Rosetta/Features/Chats/ChatDetail/ChatDetailView.swift
index 2630f16..9e4d47f 100644
--- a/Rosetta/Features/Chats/ChatDetail/ChatDetailView.swift
+++ b/Rosetta/Features/Chats/ChatDetail/ChatDetailView.swift
@@ -129,9 +129,9 @@ struct ChatDetailView: View {
     private var maxBubbleWidth: CGFloat {
         let w = UIScreen.main.bounds.width
         if w <= 500 {
-            return max(240, min(w * 0.78, w - 86))
+            return max(224, min(w * 0.72, w - 104))
         }
-        return min(w * 0.72, 520)
+        return min(w * 0.66, 460)
     }
 
     /// Visual chat content: messages list + gradient overlays + background.
diff --git a/Rosetta/Features/Chats/ChatDetail/NativeMessageCell.swift b/Rosetta/Features/Chats/ChatDetail/NativeMessageCell.swift
index 837f66a..f27ec60 100644
--- a/Rosetta/Features/Chats/ChatDetail/NativeMessageCell.swift
+++ b/Rosetta/Features/Chats/ChatDetail/NativeMessageCell.swift
@@ -163,7 +163,10 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
     private var photoTileImageViews: [UIImageView] = []
     private var photoTilePlaceholderViews: [UIView] = []
     private var photoTileActivityIndicators: [UIActivityIndicatorView] = []
+    private var photoTileErrorViews: [UIImageView] = []
     private var photoTileButtons: [UIButton] = []
+    private let photoUploadingOverlayView = UIView()
+    private let photoUploadingIndicator = UIActivityIndicatorView(style: .medium)
     private let photoOverflowOverlayView = UIView()
     private let photoOverflowLabel = UILabel()
 
@@ -195,6 +198,7 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
     private var photoLoadTasks: [String: Task<Void, Never>] = [:]
     private var photoDownloadTasks: [String: Task<Void, Never>] = [:]
     private var downloadingAttachmentIds: Set<String> = []
+    private var failedAttachmentIds: Set<String> = []
 
     // MARK: - Init
 
@@ -230,8 +234,9 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
         bubbleView.addSubview(textLabel)
 
         // Timestamp
-        statusBackgroundView.backgroundColor = UIColor.black.withAlphaComponent(0.32)
-        statusBackgroundView.layer.cornerRadius = 6
+        statusBackgroundView.backgroundColor = UIColor.black.withAlphaComponent(0.3)
+        statusBackgroundView.layer.cornerRadius = 7
+        statusBackgroundView.layer.cornerCurve = .continuous
         statusBackgroundView.isHidden = true
         bubbleView.addSubview(statusBackgroundView)
 
@@ -281,6 +286,11 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
             indicator.isHidden = true
             photoContainer.addSubview(indicator)
 
+            let errorView = UIImageView(image: Self.errorIcon)
+            errorView.contentMode = .center
+            errorView.isHidden = true
+            photoContainer.addSubview(errorView)
+
             let button = UIButton(type: .custom)
             button.tag = index
             button.isHidden = true
@@ -290,9 +300,20 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
             photoTileImageViews.append(imageView)
             photoTilePlaceholderViews.append(placeholderView)
             photoTileActivityIndicators.append(indicator)
+            photoTileErrorViews.append(errorView)
             photoTileButtons.append(button)
         }
 
+        photoUploadingOverlayView.backgroundColor = UIColor.black.withAlphaComponent(0.22)
+        photoUploadingOverlayView.isHidden = true
+        photoUploadingOverlayView.isUserInteractionEnabled = false
+        photoContainer.addSubview(photoUploadingOverlayView)
+
+        photoUploadingIndicator.color = .white
+        photoUploadingIndicator.hidesWhenStopped = true
+        photoUploadingIndicator.isHidden = true
+        photoContainer.addSubview(photoUploadingIndicator)
+
         photoOverflowOverlayView.backgroundColor = UIColor.black.withAlphaComponent(0.45)
         photoOverflowOverlayView.layer.cornerCurve = .continuous
         photoOverflowOverlayView.layer.cornerRadius = 0
@@ -516,11 +537,23 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
         bubbleLayer.shadowPath = bubbleLayer.path
         bubbleOutlineLayer.frame = bubbleView.bounds
         bubbleOutlineLayer.path = bubbleLayer.path
-        if layout.hasTail {
+        let hasPhotoContent = layout.hasPhoto
+        if hasPhotoContent {
+            bubbleLayer.shadowOpacity = 0.04
+            bubbleLayer.shadowRadius = 0.4
+            bubbleLayer.shadowOffset = CGSize(width: 0, height: 0.2)
+            bubbleOutlineLayer.strokeColor = UIColor.clear.cgColor
+        } else if layout.hasTail {
             // Tail path is appended as a second subpath; stroking it produces
             // a visible seam at the junction. Keep fill-only for tailed bubbles.
+            bubbleLayer.shadowOpacity = 0.12
+            bubbleLayer.shadowRadius = 0.6
+            bubbleLayer.shadowOffset = CGSize(width: 0, height: 0.4)
             bubbleOutlineLayer.strokeColor = UIColor.clear.cgColor
         } else {
+            bubbleLayer.shadowOpacity = 0.12
+            bubbleLayer.shadowRadius = 0.6
+            bubbleLayer.shadowOffset = CGSize(width: 0, height: 0.4)
             bubbleOutlineLayer.strokeColor = UIColor.black.withAlphaComponent(
                 layout.isOutgoing ? 0.16 : 0.22
             ).cgColor
@@ -732,6 +765,7 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
             task.cancel()
             photoDownloadTasks.removeValue(forKey: attachmentId)
             downloadingAttachmentIds.remove(attachmentId)
+            failedAttachmentIds.remove(attachmentId)
         }
 
         for index in 0..<photoTileImageViews.count {
@@ -739,6 +773,7 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
             let imageView = photoTileImageViews[index]
             let placeholderView = photoTilePlaceholderViews[index]
             let indicator = photoTileActivityIndicators[index]
+            let errorView = photoTileErrorViews[index]
             let button = photoTileButtons[index]
 
             button.isHidden = !isActiveTile
@@ -749,29 +784,42 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
                 placeholderView.isHidden = true
                 indicator.stopAnimating()
                 indicator.isHidden = true
+                errorView.isHidden = true
                 continue
             }
 
             let attachment = photoAttachments[index]
             if let cached = AttachmentCache.shared.loadImage(forAttachmentId: attachment.id) {
+                failedAttachmentIds.remove(attachment.id)
                 setPhotoTileImage(cached, at: index, animated: false)
                 placeholderView.isHidden = true
                 indicator.stopAnimating()
                 indicator.isHidden = true
+                errorView.isHidden = true
             } else {
                 setPhotoTileImage(Self.blurHashImage(from: attachment.preview), at: index, animated: false)
                 placeholderView.isHidden = imageView.image != nil
-                if downloadingAttachmentIds.contains(attachment.id) {
+                let hasFailed = failedAttachmentIds.contains(attachment.id)
+                if hasFailed {
+                    indicator.stopAnimating()
+                    indicator.isHidden = true
+                    errorView.isHidden = false
+                } else if downloadingAttachmentIds.contains(attachment.id) {
                     indicator.startAnimating()
                     indicator.isHidden = false
+                    errorView.isHidden = true
                 } else {
                     indicator.stopAnimating()
                     indicator.isHidden = true
+                    errorView.isHidden = true
                 }
                 startPhotoLoadTask(attachment: attachment)
             }
         }
         layoutPhotoOverflowOverlay()
+        updatePhotoUploadingOverlay(
+            isVisible: layout.isOutgoing && message.deliveryStatus == .waiting
+        )
     }
 
     private func layoutPhotoTiles() {
@@ -783,7 +831,19 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
             photoTilePlaceholderViews[index].frame = frame
             photoTileButtons[index].frame = frame
             photoTileActivityIndicators[index].center = CGPoint(x: frame.midX, y: frame.midY)
+            photoTileErrorViews[index].frame = CGRect(
+                x: frame.midX - 10, y: frame.midY - 10,
+                width: 20, height: 20
+            )
         }
+        photoUploadingOverlayView.frame = photoContainer.bounds
+        photoUploadingIndicator.center = CGPoint(
+            x: photoContainer.bounds.midX,
+            y: photoContainer.bounds.midY
+        )
+        photoContainer.bringSubviewToFront(photoUploadingOverlayView)
+        photoContainer.bringSubviewToFront(photoUploadingIndicator)
+        photoContainer.bringSubviewToFront(photoOverflowOverlayView)
         layoutPhotoOverflowOverlay(frames: frames)
     }
 
@@ -795,14 +855,21 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
 
         let inset: CGFloat = 2
         let r: CGFloat = max(16 - inset, 0)
-        let s: CGFloat = max(8 - inset, 0)
+        let s: CGFloat = max(5 - inset, 0)
+        let tailJoin: CGFloat = max(10 - inset, 0)
         let rect = photoContainer.bounds
         let (tl, tr, bl, br): (CGFloat, CGFloat, CGFloat, CGFloat) = {
             switch layout.position {
-            case .single: return (r, r, r, r)
+            case .single:
+                return layout.isOutgoing
+                    ? (r, r, r, tailJoin)
+                    : (r, r, tailJoin, r)
             case .top: return layout.isOutgoing ? (r, r, r, s) : (r, r, s, r)
             case .mid: return layout.isOutgoing ? (r, s, r, s) : (s, r, s, r)
-            case .bottom: return layout.isOutgoing ? (r, s, r, r) : (s, r, r, r)
+            case .bottom:
+                return layout.isOutgoing
+                    ? (r, s, r, tailJoin)
+                    : (s, r, tailJoin, r)
             }
         }()
 
@@ -950,6 +1017,17 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
         photoOverflowLabel.frame = photoOverflowOverlayView.bounds
     }
 
+    private func updatePhotoUploadingOverlay(isVisible: Bool) {
+        photoUploadingOverlayView.isHidden = !isVisible
+        if isVisible {
+            photoUploadingIndicator.isHidden = false
+            photoUploadingIndicator.startAnimating()
+        } else {
+            photoUploadingIndicator.stopAnimating()
+            photoUploadingIndicator.isHidden = true
+        }
+    }
+
     private func tileIndex(for attachmentId: String) -> Int? {
         photoAttachments.firstIndex(where: { $0.id == attachmentId })
     }
@@ -972,10 +1050,12 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
                       let loaded else {
                     return
                 }
+                self.failedAttachmentIds.remove(attachmentId)
                 self.setPhotoTileImage(loaded, at: tileIndex, animated: true)
                 self.photoTilePlaceholderViews[tileIndex].isHidden = true
                 self.photoTileActivityIndicators[tileIndex].stopAnimating()
                 self.photoTileActivityIndicators[tileIndex].isHidden = true
+                self.photoTileErrorViews[tileIndex].isHidden = true
             }
         }
     }
@@ -986,14 +1066,22 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
         guard !tag.isEmpty,
               let storedPassword = message.attachmentPassword,
               !storedPassword.isEmpty else {
+            failedAttachmentIds.insert(attachment.id)
+            if let tileIndex = tileIndex(for: attachment.id), tileIndex < photoTileErrorViews.count {
+                photoTileActivityIndicators[tileIndex].stopAnimating()
+                photoTileActivityIndicators[tileIndex].isHidden = true
+                photoTileErrorViews[tileIndex].isHidden = false
+            }
             return
         }
 
         let attachmentId = attachment.id
+        failedAttachmentIds.remove(attachmentId)
         downloadingAttachmentIds.insert(attachmentId)
         if let tileIndex = tileIndex(for: attachmentId), tileIndex < photoTileActivityIndicators.count {
             photoTileActivityIndicators[tileIndex].startAnimating()
             photoTileActivityIndicators[tileIndex].isHidden = false
+            photoTileErrorViews[tileIndex].isHidden = true
         }
 
         photoDownloadTasks[attachmentId] = Task { [weak self] in
@@ -1011,9 +1099,14 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
                         return
                     }
                     if let image {
+                        self.failedAttachmentIds.remove(attachmentId)
                         AttachmentCache.shared.saveImage(image, forAttachmentId: attachmentId)
                         self.setPhotoTileImage(image, at: tileIndex, animated: true)
                         self.photoTilePlaceholderViews[tileIndex].isHidden = true
+                        self.photoTileErrorViews[tileIndex].isHidden = true
+                    } else {
+                        self.failedAttachmentIds.insert(attachmentId)
+                        self.photoTileErrorViews[tileIndex].isHidden = false
                     }
                     self.photoTileActivityIndicators[tileIndex].stopAnimating()
                     self.photoTileActivityIndicators[tileIndex].isHidden = true
@@ -1023,12 +1116,14 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
                     guard let self else { return }
                     self.photoDownloadTasks.removeValue(forKey: attachmentId)
                     self.downloadingAttachmentIds.remove(attachmentId)
+                    self.failedAttachmentIds.insert(attachmentId)
                     guard let tileIndex = self.tileIndex(for: attachmentId),
                           tileIndex < self.photoTileActivityIndicators.count else {
                         return
                     }
                     self.photoTileActivityIndicators[tileIndex].stopAnimating()
                     self.photoTileActivityIndicators[tileIndex].isHidden = true
+                    self.photoTileErrorViews[tileIndex].isHidden = false
                 }
             }
         }
@@ -1046,7 +1141,9 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
         }
         photoDownloadTasks.removeAll()
         downloadingAttachmentIds.removeAll()
+        failedAttachmentIds.removeAll()
         photoContainer.layer.mask = nil
+        updatePhotoUploadingOverlay(isVisible: false)
         photoOverflowOverlayView.isHidden = true
         photoOverflowLabel.isHidden = true
         photoOverflowLabel.text = nil
@@ -1057,6 +1154,7 @@ final class NativeMessageCell: UICollectionViewCell, UIContextMenuInteractionDel
             photoTilePlaceholderViews[index].isHidden = true
             photoTileActivityIndicators[index].stopAnimating()
             photoTileActivityIndicators[index].isHidden = true
+            photoTileErrorViews[index].isHidden = true
             photoTileButtons[index].isHidden = true
         }
     }
@@ -1271,7 +1369,7 @@ extension NativeMessageCell: UIGestureRecognizerDelegate {
 final class BubblePathCache {
     static let shared = BubblePathCache()
 
-    private let pathVersion = 7
+    private let pathVersion = 8
     private var cache: [String: CGPath] = [:]
 
     func path(
@@ -1296,7 +1394,7 @@ final class BubblePathCache {
     private func makeBubblePath(
         in rect: CGRect, position: BubblePosition, isOutgoing: Bool, hasTail: Bool
     ) -> CGPath {
-        let r: CGFloat = 16, s: CGFloat = 8, tailW: CGFloat = 6
+        let r: CGFloat = 16, s: CGFloat = 5, tailW: CGFloat = 6
 
         // Body rect
         let bodyRect: CGRect