diff --git a/common.gypi b/common.gypi
index 9861a1bcb493..d153c79d3e32 100644
--- a/common.gypi
+++ b/common.gypi
@@ -186,5 +186,16 @@
         ],
       },
     }],  # msvs_express==1
+    # The breakdpad on Windows assumes Debug_x64 and Release_x64 configurations.
+    ['OS=="win"', {
+      'target_defaults': {
+        'configurations': {
+          'Debug_x64': {
+          },
+          'Release_x64': {
+          },
+        },
+      },
+    }],  # OS=="win"
   ],
 }
diff --git a/script/bootstrap.py b/script/bootstrap.py
index 4ee47787effe..10dfde5b3dd4 100755
--- a/script/bootstrap.py
+++ b/script/bootstrap.py
@@ -58,7 +58,7 @@ def bootstrap_brightray(url):
 def update_apm():
   ## NB: Without this, subprocess incorrectly searches for npm.exe
   npm_cmd = 'npm'
-  if sys.platform == 'win32':
+  if sys.platform in ['win32', 'cygwin']:
     npm_cmd += '.cmd'
 
   with scoped_cwd(os.path.join('vendor', 'apm')):