diff --git a/engine/src/flutter/tools/mojo_cache_linker.py b/engine/src/flutter/tools/mojo_cache_linker.py
index d848ecdf84..783377479e 100755
--- a/engine/src/flutter/tools/mojo_cache_linker.py
+++ b/engine/src/flutter/tools/mojo_cache_linker.py
@@ -9,6 +9,7 @@ import os
 import sys
 import subprocess
 import json
+import platform
 
 
 def library_paths(build_dir):
@@ -44,10 +45,14 @@ def compute_path_to_app_id_map(paths, cache, cache_mtime):
     for path in paths:
         app_id = get_cached_app_id(path, cache, cache_mtime)
         if not app_id:
-            logging.info('sha256sum %s' % path)
+            if platform.system() == 'Darwin':
+                logging.info('shasum -a 256 %s' % path)
+                output = subprocess.check_output(['shasum', '-a', '256', path])
+            else:
+                logging.info('sha256sum %s' % path)
+                output = subprocess.check_output(['sha256sum', path])
             # Example output:
             # f82a3551478a9a0e010adccd675053b9 png_viewer.mojo
-            output = subprocess.check_output(['sha256sum', path])
             app_id = output.strip().split()[0]
         path_to_app_id_map[path] = app_id
     return path_to_app_id_map
diff --git a/engine/src/flutter/tools/skydb b/engine/src/flutter/tools/skydb
index faac8bac7c..e99509d762 100755
--- a/engine/src/flutter/tools/skydb
+++ b/engine/src/flutter/tools/skydb
@@ -18,6 +18,7 @@ import subprocess
 import sys
 import time
 import urlparse
+import platform
 
 SUPPORTED_MIME_TYPES = [
     'text/html',
@@ -531,9 +532,14 @@ class SkyDebugger(object):
             symbol_search_paths = system_lib_dirs + symbol_search_paths
 
             # TODO(eseidel): We need to look up the toolchain somehow?
-            gdb_path = os.path.join(SRC_ROOT, 'third_party/android_tools/ndk/'
-                'toolchains/arm-linux-androideabi-4.9/prebuilt/linux-x86_64/'
-                'bin/arm-linux-androideabi-gdb')
+            if platform.system() == 'Darwin':
+                gdb_path = os.path.join(SRC_ROOT, 'third_party/android_tools/ndk/'
+                    'toolchains/arm-linux-androideabi-4.9/prebuilt/darwin-x86_64/'
+                    'bin/arm-linux-androideabi-gdb')
+            else:
+                gdb_path = os.path.join(SRC_ROOT, 'third_party/android_tools/ndk/'
+                    'toolchains/arm-linux-androideabi-4.9/prebuilt/linux-x86_64/'
+                    'bin/arm-linux-androideabi-gdb')
 
         # Set solib-search-path after letting android modify symbol_search_paths
         eval_commands.append(