diff --git a/build/vs_toolchain.py b/build/vs_toolchain.py
index b754f6edd7f52f..2ebd520102be97 100755
--- a/build/vs_toolchain.py
+++ b/build/vs_toolchain.py
@@ -408,7 +408,9 @@ def _CopyDebugger(target_dir, target_cpu):
 
   # List of debug files that should be copied, the first element of the tuple is
   # the name of the file and the second indicates if it's optional.
-  debug_files = [('dbghelp.dll', False), ('dbgcore.dll', True)]
+  debug_files = [('dbghelp.dll', False), ('dbgcore.dll', True),
+                 ('api-ms-win-downlevel-kernel32-l2-1-0.dll', False),
+                 ('api-ms-win-eventing-provider-l1-1-0.dll', False)]
   for debug_file, is_optional in debug_files:
     full_path = os.path.join(win_sdk_dir, 'Debuggers', target_cpu, debug_file)
     if not os.path.exists(full_path):
@@ -418,7 +420,7 @@ def _CopyDebugger(target_dir, target_cpu):
         # TODO(crbug.com/773476): remove version requirement.
         raise Exception('%s not found in "%s"\r\nYou must install the '
                         '"Debugging Tools for Windows" feature from the Windows'
-                        ' 10 SDK.'
+                        ' 10 SDK, the 10.0.19041.0 version.'
                         % (debug_file, full_path))
     target_path = os.path.join(target_dir, debug_file)
     _CopyRuntimeImpl(target_path, full_path)
@@ -438,12 +440,11 @@ def _GetDesiredVsToolchainHashes():
   * //docs/windows_build_instructions.md mentions of VS or Windows SDK.
     Keeps the document consistent with the toolchain version.
   """
-  # VS 2019 Update 9 (16.3.29324.140) with 10.0.18362 SDK, 10.0.17763 version of
-  # Debuggers, and 10.0.17134 version of d3dcompiler_47.dll, with ARM64
-  # libraries and UWP support.
+  # VS 2019 16.61 with 10.0.19041 SDK, and 10.0.17134 version of
+  # d3dcompiler_47.dll, with ARM64 libraries and UWP support.
   # See go/chromium-msvc-toolchain for instructions about how to update the
   # toolchain.
-  toolchain_hash = '9ff60e43ba91947baca460d0ca3b1b980c3a2c23'
+  toolchain_hash = 'a687d8e2e4114d9015eb550e1b156af21381faac'
   # Third parties that do not have access to the canonical toolchain can map
   # canonical toolchain version to their own toolchain versions.
   toolchain_hash_mapping_key = 'GYP_MSVS_HASH_%s' % toolchain_hash
diff --git a/build/win/BUILD.gn b/build/win/BUILD.gn
index e4902041a0d506..d449f592519daf 100644
--- a/build/win/BUILD.gn
+++ b/build/win/BUILD.gn
@@ -79,6 +79,7 @@ if (is_win) {
         "$root_out_dir/cdb/api-ms-win-crt-string-l1-1-0.dll",
         "$root_out_dir/cdb/api-ms-win-crt-time-l1-1-0.dll",
         "$root_out_dir/cdb/api-ms-win-crt-utility-l1-1-0.dll",
+        "$root_out_dir/cdb/api-ms-win-downlevel-kernel32-l2-1-0.dll",
         "$root_out_dir/cdb/api-ms-win-eventing-provider-l1-1-0.dll",
         "$root_out_dir/cdb/ucrtbase.dll",
       ]
@@ -162,6 +163,8 @@ if (is_win) {
           "$root_out_dir/api-ms-win-crt-string-l1-1-0.dll",
           "$root_out_dir/api-ms-win-crt-time-l1-1-0.dll",
           "$root_out_dir/api-ms-win-crt-utility-l1-1-0.dll",
+          "$root_out_dir/api-ms-win-downlevel-kernel32-l2-1-0.dll",
+          "$root_out_dir/api-ms-win-eventing-provider-l1-1-0.dll",
         ]
         if (!is_debug) {
           data += [ "$root_out_dir/ucrtbase.dll" ]