diff --git a/web/src/api/chats.ts b/web/src/api/chats.ts
index d65c6e6..cfec78f 100644
--- a/web/src/api/chats.ts
+++ b/web/src/api/chats.ts
@@ -104,17 +104,32 @@ export async function uploadToPresignedUrl(
   uploadUrl: string,
   requiredHeaders: Record<string, string>,
   file: File,
-  onProgress?: (percent: number) => void
+  onProgress?: (percent: number) => void,
+  retries = 2
 ): Promise<void> {
-  await axios.put(uploadUrl, file, {
-    headers: requiredHeaders,
-    onUploadProgress: (progressEvent) => {
-      if (!onProgress || !progressEvent.total) {
-        return;
+  let attempt = 0;
+  while (attempt <= retries) {
+    try {
+      await axios.put(uploadUrl, file, {
+        headers: requiredHeaders,
+        onUploadProgress: (progressEvent) => {
+          if (!onProgress || !progressEvent.total) {
+            return;
+          }
+          onProgress(Math.round((progressEvent.loaded * 100) / progressEvent.total));
+        }
+      });
+      return;
+    } catch (error) {
+      const status = axios.isAxiosError(error) ? error.response?.status : undefined;
+      const retryable = status === undefined || status >= 500;
+      if (!retryable || attempt >= retries) {
+        throw error;
       }
-      onProgress(Math.round((progressEvent.loaded * 100) / progressEvent.total));
+      attempt += 1;
+      await new Promise((resolve) => window.setTimeout(resolve, 400 * attempt));
     }
-  });
+  }
 }
 
 export async function attachFile(messageId: number, fileUrl: string, fileType: string, fileSize: number): Promise<void> {
diff --git a/web/src/components/MessageComposer.tsx b/web/src/components/MessageComposer.tsx
index 7a20f06..320c145 100644
--- a/web/src/components/MessageComposer.tsx
+++ b/web/src/components/MessageComposer.tsx
@@ -77,7 +77,21 @@ export function MessageComposer() {
     const replyToMessageId = activeChatId ? (replyToByChat[activeChatId]?.id ?? undefined) : undefined;
     addOptimisticMessage({ chatId: activeChatId, senderId: me.id, type: "text", text: textValue, clientMessageId });
     try {
-      const message = await sendMessageWithClientId(activeChatId, textValue, "text", clientMessageId, replyToMessageId);
+      let message = null;
+      for (let attempt = 0; attempt < 2; attempt += 1) {
+        try {
+          message = await sendMessageWithClientId(activeChatId, textValue, "text", clientMessageId, replyToMessageId);
+          break;
+        } catch (error) {
+          if (attempt === 1) {
+            throw error;
+          }
+          await new Promise((resolve) => window.setTimeout(resolve, 250));
+        }
+      }
+      if (!message) {
+        throw new Error("send failed");
+      }
       confirmMessageByClientId(activeChatId, clientMessageId, message);
       setText("");
       clearDraft(activeChatId);
@@ -110,8 +124,12 @@ export function MessageComposer() {
         clientMessageId
       });
       const message = await sendMessageWithClientId(activeChatId, upload.file_url, messageType, clientMessageId, replyToMessageId);
-      await attachFile(message.id, upload.file_url, file.type || "application/octet-stream", file.size);
       confirmMessageByClientId(activeChatId, clientMessageId, message);
+      try {
+        await attachFile(message.id, upload.file_url, file.type || "application/octet-stream", file.size);
+      } catch {
+        setUploadError("File sent, but metadata save failed. Please refresh chat.");
+      }
       setReplyToMessage(activeChatId, null);
     } catch {
       removeOptimisticMessage(activeChatId, clientMessageId);