diff --git a/setup/installer/osx/app/main.py b/setup/installer/osx/app/main.py
index e7c38b65fb..e21a66e510 100644
--- a/setup/installer/osx/app/main.py
+++ b/setup/installer/osx/app/main.py
@@ -654,8 +654,14 @@ class Py2App(object):
         shutil.copytree(d, appdir, symlinks=True)
         subprocess.check_call(['/Users/kovid/sign.sh', appdir])
         os.symlink('/Applications', os.path.join(tdir, 'Applications'))
-        subprocess.check_call(['/usr/bin/hdiutil', 'create', '-srcfolder', tdir,
-                               '-volname', volname, '-format', format, dmg])
+        size_in_mb = int(subprocess.check_output(['du', '-s', '-k', tdir]).decode('utf-8').split()[0]) / 1024.
+        cmd = ['/usr/bin/hdiutil', 'create', '-srcfolder', tdir, '-volname', volname, '-format', format]
+        if 190 < size_in_mb < 250:
+            # We need -size 255m because of a bug in hdiutil. When the size of
+            # srcfolder is close to 200MB hdiutil fails with
+            # diskimages-helper: resize request is above maximum size allowed.
+            cmd += ['-size', '255m']
+        subprocess.check_call(cmd + [dmg])
         shutil.rmtree(tdir)
         if internet_enable:
             subprocess.check_call(['/usr/bin/hdiutil', 'internet-enable', '-yes', dmg])