diff --git a/chrome/browser/safe_browsing/download_protection_service.cc b/chrome/browser/safe_browsing/download_protection_service.cc
index ee01b97dc79e9..1460b2f7606f2 100644
--- a/chrome/browser/safe_browsing/download_protection_service.cc
+++ b/chrome/browser/safe_browsing/download_protection_service.cc
@@ -771,12 +771,12 @@ class DownloadProtectionService::CheckClientDownloadRequest
     request.mutable_signature()->CopyFrom(signature_info_);
     if (image_headers_)
       request.set_allocated_image_headers(image_headers_.release());
+    if (zipped_executable_)
+      request.mutable_archived_binary()->Swap(&archived_binary_);
     if (!request.SerializeToString(&client_download_request_data_)) {
       FinishRequest(UNKNOWN, REASON_INVALID_REQUEST_PROTO);
       return;
     }
-    if (zipped_executable_)
-      request.mutable_archived_binary()->Swap(&archived_binary_);
     service_->client_download_request_callbacks_.Notify(item_, &request);
 
     DVLOG(2) << "Sending a request for URL: "
diff --git a/chrome/browser/safe_browsing/download_protection_service_unittest.cc b/chrome/browser/safe_browsing/download_protection_service_unittest.cc
index bc1568f292abf..2044d65b5aecd 100644
--- a/chrome/browser/safe_browsing/download_protection_service_unittest.cc
+++ b/chrome/browser/safe_browsing/download_protection_service_unittest.cc
@@ -4,6 +4,7 @@
 
 #include "chrome/browser/safe_browsing/download_protection_service.h"
 
+#include <stdint.h>
 #include <map>
 #include <string>
 
@@ -279,6 +280,16 @@ class DownloadProtectionServiceTest : public testing::Test {
     return false;
   }
 
+  static const ClientDownloadRequest_ArchivedBinary* GetRequestArchivedBinary(
+      const ClientDownloadRequest& request,
+      const std::string& file_basename) {
+    for (const auto& archived_binary : request.archived_binary()) {
+      if (archived_binary.file_basename() == file_basename)
+        return &archived_binary;
+    }
+    return nullptr;
+  }
+
   // Flushes any pending tasks in the message loops of all threads.
   void FlushThreadMessageLoops() {
     BrowserThread::GetBlockingPool()->FlushForTesting();
@@ -1113,6 +1124,15 @@ TEST_F(DownloadProtectionServiceTest, CheckClientDownloadZip) {
 #if defined(OS_WIN) || defined(OS_MACOSX)
   // OSX sends pings for evaluation purposes.
   EXPECT_TRUE(HasClientDownloadRequest());
+  const ClientDownloadRequest& request = *GetClientDownloadRequest();
+  EXPECT_EQ(1, request.archived_binary_size());
+  const ClientDownloadRequest_ArchivedBinary* archived_binary =
+      GetRequestArchivedBinary(request, "file.exe");
+  ASSERT_NE(nullptr, archived_binary);
+  EXPECT_EQ(ClientDownloadRequest_DownloadType_WIN_EXECUTABLE,
+            archived_binary->download_type());
+  EXPECT_EQ(static_cast<int64_t>(file_contents.size()),
+            archived_binary->length());
   ClearClientDownloadRequest();
 #else
   EXPECT_FALSE(HasClientDownloadRequest());