diff --git a/packages/web/src/components/chat/Message.tsx b/packages/web/src/components/chat/Message.tsx
index 61b0dfb8..fc7c27e3 100644
--- a/packages/web/src/components/chat/Message.tsx
+++ b/packages/web/src/components/chat/Message.tsx
@@ -132,6 +132,13 @@ export function Message({ message, isCompact, isFirstInGroup, previousMessageId
   const pending = isPendingMessage(message) ? message.__pending : null;
   const showInteractions = !pending;
 
+  const transfersForRow = useTransferStore((s) => s.transfers);
+  const anyTransferTerminallyBad = !!pending && pending.transferIds.some((tid) => {
+    const t = transfersForRow.get(tid);
+    return t && (t.state === 'failed' || t.state === 'aborted');
+  });
+  const showRetryDiscardRow = pending?.state === 'failed' || anyTransferTerminallyBad;
+
   const channelKey: string = isPendingMessage(message)
     ? message.channelId || message.dmChannelId || ''
     : message.channelId || (message as MessageWithUser & { dmChannelId?: string }).dmChannelId || '';
@@ -503,7 +510,7 @@ export function Message({ message, isCompact, isFirstInGroup, previousMessageId
             )}
 
             {/* Failed-state retry/discard row */}
-            {pending?.state === 'failed' && (
+            {showRetryDiscardRow && pending && (
               <div className="mt-1 flex gap-2 px-2 py-1 rounded-md bg-accent-rose/15 text-xs">
                 <button
                   onClick={async () => {
diff --git a/packages/web/src/stores/pendingMessageRehydrate.ts b/packages/web/src/stores/pendingMessageRehydrate.ts
index 1d456fe4..c0583d26 100644
--- a/packages/web/src/stores/pendingMessageRehydrate.ts
+++ b/packages/web/src/stores/pendingMessageRehydrate.ts
@@ -43,6 +43,23 @@ export function startPendingMessageOrchestrator(): void {
     if (sig === lastStateSig) return;
     lastStateSig = sig;
 
+    // Mark bubbles as 'failed' when any of their transfers are in a terminal-failure
+    // state (aborted or failed). This surfaces the retry/discard row in Message.tsx
+    // instead of leaving the bubble stuck in 'sending' forever.
+    const allTransfers = useTransferStore.getState().transfers;
+    for (const list of usePendingMessageStore.getState().bubbles.values()) {
+      for (const b of list) {
+        if (b.state !== 'sending') continue;
+        const anyBad = b.transferIds.some((tid) => {
+          const t = allTransfers.get(tid);
+          return t && (t.state === 'failed' || t.state === 'aborted');
+        });
+        if (anyBad) {
+          usePendingMessageStore.getState().markFailed(b.clientId);
+        }
+      }
+    }
+
     const fresh = usePendingMessageStore.getState().listReadyForDeferredSend();
     for (const b of fresh) {
       if (!sentClientIds.has(b.clientId)) {
diff --git a/packages/web/src/stores/transferStore.ts b/packages/web/src/stores/transferStore.ts
index f38d1ea4..48eb20be 100644
--- a/packages/web/src/stores/transferStore.ts
+++ b/packages/web/src/stores/transferStore.ts
@@ -87,6 +87,12 @@ function uuid(): string {
 // Live tus Upload instances — keyed by transferId. Not serializable, never persisted.
 const liveUploads = new Map<string, Upload>();
 
+// Original File/Blob references — keyed by transferId. Survive pause; cleared
+// on abort or success. Used for in-session resume when no FileSystemFileHandle exists
+// (file picker, paste, or drag-drop on Firefox/Safari). Cross-reload resume still
+// requires a handle — that path uses idbHandles.
+const liveUploadFiles = new Map<string, Blob>();
+
 // Live download AbortControllers — keyed by transferId. Not serializable, never persisted.
 const liveDownloads = new Map<string, AbortController>();
 
@@ -254,6 +260,7 @@ export const useTransferStore = create<TransferStore>()(
               get().setError(id, { message: msg, permanent: true });
             } finally {
               liveUploads.delete(id);
+              liveUploadFiles.delete(id);
             }
           },
           onError: (err: Error) => {
@@ -267,6 +274,7 @@ export const useTransferStore = create<TransferStore>()(
 
         const upload = new Upload(file as File, tusOpts);
         liveUploads.set(id, upload);
+        liveUploadFiles.set(id, file);
         upload.start();
         return id;
       },
@@ -279,6 +287,7 @@ export const useTransferStore = create<TransferStore>()(
           void u.abort(true).catch(() => { /* server may be unreachable; that's OK */ });
           liveUploads.delete(id);
         }
+        liveUploadFiles.delete(id);
         get().setState_(id, 'aborted');
       },
 
@@ -310,9 +319,12 @@ export const useTransferStore = create<TransferStore>()(
           return;
         }
 
-        // Try to reacquire the file via the persisted FileSystemFileHandle.
-        let blob: Blob | undefined;
-        if (t.fileHandleId) {
+        // Try in-memory File (same-session resume — file picker, paste, browsers
+        // without getAsFileSystemHandle).
+        let blob: Blob | undefined = liveUploadFiles.get(id);
+
+        // Fall back to persisted FileSystemFileHandle (cross-reload resume on Chrome/Edge).
+        if (!blob && t.fileHandleId) {
           const { getHandle, ensurePermission } = await import('../utils/idbHandles');
           const handle = await getHandle(t.fileHandleId);
           if (handle) {
@@ -327,7 +339,9 @@ export const useTransferStore = create<TransferStore>()(
         }
 
         if (!blob) {
-          // No handle path — UI surfaces "re-pick to resume". Stay paused.
+          // No handle, no in-memory file — surface "re-pick to resume" to the user.
+          // (Cross-reload on Firefox/Safari or after MessageInput unmount that cleared
+          // its preview-URL ref will land here.)
           get().setState_(id, 'paused');
           return;
         }
@@ -354,6 +368,7 @@ export const useTransferStore = create<TransferStore>()(
               get().setError(id, { message: msg, permanent: true });
             } finally {
               liveUploads.delete(id);
+              liveUploadFiles.delete(id);
             }
           },
           onError: (err: Error) => {