diff --git a/lib/client/upload-with-retry.ts b/lib/client/upload-with-retry.ts
index 095bf703c..4690aad1c 100644
--- a/lib/client/upload-with-retry.ts
+++ b/lib/client/upload-with-retry.ts
@@ -10,6 +10,7 @@ const CLIENT_UPLOAD_ID_FIELD = "clientUploadId";
 const DIRECT_UPLOAD_INITIATE_TIMEOUT_MS = 3 * 1000;
 const DIRECT_UPLOAD_ACTION_TIMEOUT_MS = 15 * 1000;
 const DIRECT_UPLOAD_ABORT_TIMEOUT_MS = 8 * 1000;
+const DIRECT_UPLOAD_STALL_TIMEOUT_MS = 10 * 1000;
 const XHR_UPLOAD_TOTAL_TIMEOUT_MS = 6 * 60 * 1000;
 const XHR_UPLOAD_STALL_TIMEOUT_MS = 30 * 1000;
 
@@ -336,6 +337,7 @@ async function fetchWithControlTimeout(
   const controller = new AbortController();
   let timeout: ReturnType<typeof setTimeout> | null = null;
   let timedOut = false;
+  let settled = false;
 
   const onAbort = () => {
     controller.abort();
@@ -344,30 +346,44 @@ async function fetchWithControlTimeout(
   signal?.addEventListener("abort", onAbort, { once: true });
 
   try {
-    timeout = setTimeout(() => {
-      timedOut = true;
-      controller.abort();
-    }, timeoutMs);
-
-    return await fetch(input, {
+    const request = fetch(input, {
       ...init,
       signal: controller.signal,
+    }).catch((error) => {
+      if (signal?.aborted) {
+        throw createAbortError();
+      }
+
+      if (timedOut) {
+        throw createTimeoutError(
+          `Direct upload control request timed out after ${Math.round(
+            timeoutMs / 1000
+          )}s`
+        );
+      }
+
+      throw error;
     });
-  } catch (error) {
-    if (signal?.aborted) {
-      throw createAbortError();
-    }
 
-    if (timedOut) {
-      throw createTimeoutError(
-        `Direct upload control request timed out after ${Math.round(
-          timeoutMs / 1000
-        )}s`
-      );
-    }
+    const timeoutPromise = new Promise<never>((_, reject) => {
+      timeout = setTimeout(() => {
+        timedOut = true;
+        controller.abort();
+        if (!settled) {
+          reject(
+            createTimeoutError(
+              `Direct upload control request timed out after ${Math.round(
+                timeoutMs / 1000
+              )}s`
+            )
+          );
+        }
+      }, timeoutMs);
+    });
 
-    throw error;
+    return await Promise.race([request, timeoutPromise]);
   } finally {
+    settled = true;
     if (timeout) {
       clearTimeout(timeout);
     }
@@ -547,7 +563,8 @@ async function fetchDirectPartWithRetry(
   },
   maxRetries: number,
   signal?: AbortSignal,
-  onProgress?: (loaded: number, total: number) => void
+  onProgress?: (loaded: number, total: number) => void,
+  options?: { stallTimeoutMs?: number }
 ) {
   for (let attempt = 0; ; attempt += 1) {
     try {
@@ -557,6 +574,7 @@ async function fetchDirectPartWithRetry(
         {
           onProgress,
           signal,
+          stallTimeoutMs: options?.stallTimeoutMs,
         }
       );
 
@@ -667,7 +685,8 @@ async function uploadMultipartParts(params: {
         params.signal,
         (loaded, total) => {
           reportPartProgress(part.partNumber, loaded, total || body.size);
-        }
+        },
+        { stallTimeoutMs: DIRECT_UPLOAD_STALL_TIMEOUT_MS }
       );
 
       if (!response.ok) {
@@ -731,6 +750,9 @@ async function fetchDirectUpload(
     );
 
     if (upload.mode === "single") {
+      emitUploadProgress(onProgress, 0, file.blob.size, "direct", {
+        percent: 2,
+      });
       const response = await fetchDirectPartWithRetry(
         upload.url,
         {
@@ -744,7 +766,8 @@ async function fetchDirectUpload(
         signal,
         (loaded, total) => {
           emitUploadProgress(onProgress, loaded, total || file.blob.size, "direct");
-        }
+        },
+        { stallTimeoutMs: DIRECT_UPLOAD_STALL_TIMEOUT_MS }
       );
 
       if (!response.ok) {
@@ -774,6 +797,9 @@ async function fetchDirectUpload(
     }
 
     multipartUpload = upload;
+    emitUploadProgress(onProgress, 0, file.blob.size, "multipart", {
+      percent: 2,
+    });
     const parts = await uploadMultipartParts({
       file,
       upload,