diff --git a/app/(chat)/api/files/direct-upload/route.ts b/app/(chat)/api/files/direct-upload/route.ts
index dff8785bd..af795c131 100644
--- a/app/(chat)/api/files/direct-upload/route.ts
+++ b/app/(chat)/api/files/direct-upload/route.ts
@@ -29,6 +29,10 @@ const DEFAULT_PART_SIZE_BYTES = 8 * 1024 * 1024;
 const PRESIGNED_URL_EXPIRES_SECONDS = 15 * 60;
 const DIRECT_UPLOAD_PREFIX = "uploads/direct";
 
+function elapsedMs(startedAt: number) {
+  return Date.now() - startedAt;
+}
+
 const allowedDirectUploadTypes = new Set([
   "image/jpeg",
   "image/jpg",
@@ -141,6 +145,7 @@ async function createPartUrls(params: {
 }
 
 export async function POST(request: Request) {
+  const requestStartedAt = Date.now();
   const session = await auth();
   if (!session?.user?.id) {
     return NextResponse.json({ error: "Unauthorized" }, { status: 401 });
@@ -159,6 +164,16 @@ export async function POST(request: Request) {
     );
   }
 
+  logger.info("direct_upload_request_start", {
+    action: payload.action,
+    size: "size" in payload ? payload.size : null,
+    contentType: "contentType" in payload ? payload.contentType : null,
+    purpose: "purpose" in payload ? payload.purpose || null : null,
+    clientUploadId:
+      "clientUploadId" in payload ? payload.clientUploadId || null : null,
+  });
+
+  const resolveStartedAt = Date.now();
   const target = await resolveS3UploadTarget().catch((error) => {
     logger.error("resolve_storage_target_failed", error);
     return null;
@@ -170,6 +185,13 @@ export async function POST(request: Request) {
       { status: 409 }
     );
   }
+  logger.info("direct_upload_storage_target_resolved", {
+    action: payload.action,
+    elapsedMs: elapsedMs(resolveStartedAt),
+    provider: target.config.provider || "s3",
+    bucket: target.config.bucket,
+    hasPublicUrl: Boolean(target.config.publicUrl),
+  });
 
   const client = createS3Client(target.config);
   const bucket = target.config.bucket;
@@ -203,6 +225,7 @@ export async function POST(request: Request) {
       );
 
       if (payload.size < MULTIPART_THRESHOLD_BYTES) {
+        const presignStartedAt = Date.now();
         const command = new PutObjectCommand({
           Bucket: bucket,
           Key: key,
@@ -213,6 +236,13 @@ export async function POST(request: Request) {
         const url = await getSignedUrl(client, command, {
           expiresIn: PRESIGNED_URL_EXPIRES_SECONDS,
         });
+        logger.info("direct_upload_single_presigned", {
+          elapsedMs: elapsedMs(presignStartedAt),
+          totalElapsedMs: elapsedMs(requestStartedAt),
+          size: payload.size,
+          contentType,
+          clientUploadId: payload.clientUploadId || null,
+        });
 
         const headers: Record<string, string> = {
           "Content-Type": contentType,
@@ -232,6 +262,7 @@ export async function POST(request: Request) {
         });
       }
 
+      const multipartStartedAt = Date.now();
       const createResult = await client.send(
         new CreateMultipartUploadCommand({
           Bucket: bucket,
@@ -256,6 +287,15 @@ export async function POST(request: Request) {
         uploadId,
         partCount,
       });
+      logger.info("direct_upload_multipart_prepared", {
+        elapsedMs: elapsedMs(multipartStartedAt),
+        totalElapsedMs: elapsedMs(requestStartedAt),
+        size: payload.size,
+        partCount,
+        partSize,
+        contentType,
+        clientUploadId: payload.clientUploadId || null,
+      });
 
       return NextResponse.json({
         mode: "multipart",
@@ -271,6 +311,7 @@ export async function POST(request: Request) {
 
     if (payload.action === "abort") {
       const key = assertUserOwnedKey(payload.key, session.user.id);
+      const abortStartedAt = Date.now();
       await client.send(
         new AbortMultipartUploadCommand({
           Bucket: bucket,
@@ -278,6 +319,11 @@ export async function POST(request: Request) {
           UploadId: payload.uploadId,
         })
       );
+      logger.info("direct_upload_multipart_aborted", {
+        elapsedMs: elapsedMs(abortStartedAt),
+        totalElapsedMs: elapsedMs(requestStartedAt),
+        clientUploadId: payload.clientUploadId || null,
+      });
       return NextResponse.json({ ok: true });
     }
 
@@ -291,6 +337,7 @@ export async function POST(request: Request) {
     }
 
     if (payload.uploadId) {
+      const completeMultipartStartedAt = Date.now();
       const parts = [...(payload.parts || [])].sort(
         (a, b) => a.PartNumber - b.PartNumber
       );
@@ -311,14 +358,25 @@ export async function POST(request: Request) {
           },
         })
       );
+      logger.info("direct_upload_multipart_completed", {
+        elapsedMs: elapsedMs(completeMultipartStartedAt),
+        partCount: parts.length,
+        clientUploadId: payload.clientUploadId || null,
+      });
     }
 
+    const headStartedAt = Date.now();
     const head = await client.send(
       new HeadObjectCommand({
         Bucket: bucket,
         Key: key,
       })
     );
+    logger.info("direct_upload_head_object_completed", {
+      elapsedMs: elapsedMs(headStartedAt),
+      uploadMode: payload.uploadId ? "multipart" : "single",
+      clientUploadId: payload.clientUploadId || null,
+    });
 
     const actualSize =
       typeof head.ContentLength === "number" ? head.ContentLength : null;
@@ -329,6 +387,7 @@ export async function POST(request: Request) {
     const url = buildS3PublicUrl(target.config, key);
     const resolvedContentType =
       head.ContentType || contentType || getContentType(payload.filename);
+    const assetStartedAt = Date.now();
     const asset = await upsertMediaAsset({
       userId: session.user.id,
       mediaType: "image",
@@ -349,6 +408,13 @@ export async function POST(request: Request) {
         clientUploadId: payload.clientUploadId || null,
       },
     });
+    logger.info("direct_upload_asset_registered", {
+      elapsedMs: elapsedMs(assetStartedAt),
+      totalElapsedMs: elapsedMs(requestStartedAt),
+      uploadMode: payload.uploadId ? "multipart" : "single",
+      assetId: asset?.id ?? null,
+      clientUploadId: payload.clientUploadId || null,
+    });
 
     await maybeEnqueueStorageMigrationTask({
       uploaded: { url, pathname: key },
diff --git a/lib/client/upload-with-retry.ts b/lib/client/upload-with-retry.ts
index b18bb82c6..095bf703c 100644
--- a/lib/client/upload-with-retry.ts
+++ b/lib/client/upload-with-retry.ts
@@ -7,6 +7,7 @@ const SERVER_UPLOAD_MAX_BYTES = 50 * 1024 * 1024;
 const DIRECT_UPLOAD_PART_CONCURRENCY = 4;
 const DIRECT_UPLOAD_SUPPRESS_MS = 2 * 60 * 1000;
 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 XHR_UPLOAD_TOTAL_TIMEOUT_MS = 6 * 60 * 1000;
@@ -725,7 +726,8 @@ async function fetchDirectUpload(
         purpose: file.purpose,
         clientUploadId: file.clientUploadId,
       },
-      signal
+      signal,
+      DIRECT_UPLOAD_INITIATE_TIMEOUT_MS
     );
 
     if (upload.mode === "single") {