I do like Option #1 since the checkbox inside a dropdown is a bit strange.

@bettes, what do you think?

My two cents: I prefer option 2. I think it's awkward either way, but there isn't much precedent for a context menu item toggling a setting (instead of taking some action, e.g. "Move up" or "Delete"). At least having it be a checkbox makes it clear what it does, so I would vote to keep the checkbox and just leave the menu open when tapping it.

BTW, this affects "Display Google Chrome in this language" too (Windows/CrOS). For that, a checkbox never made sense to me because turning the option off deosn't make much sense -- i would almost like option 1 for that one...

Last update... just dug up this: https://drive.google.com/a/google.com/file/d/0B6HSBrih6pNUNWFESGhheDZ3dm8/view?usp=sharing

In this experiment, the Translate checkbox is unchanged (closes the menu instantly), but the Display checkbox has a 100ms delay before the menu closes. It's enough for you to witness the checkbox changing state. I asked bettes@ about this, it's one of the unresolved questions in the PREVIEW-Language-1 mocks.

The delay is a nice touch and actually consistent with the cros System UI as well. If you could apply that 100ms delay on both checkboxes, that'd be the preferred course of action. 

I want to keep the checkboxes in place to minimize the iterations to this UI. There are discussions around the performance and UI benefits of "removing inline/dynamic content" from the main page which would effectively move this UI to a subpage. This isn't a launch-blocking effort at the moment, but if there's convincing wins to doing so then I'd like us to invest in that effort instead. Thank you both! 

https://folio.googleplex.com/chrome-ux-specs-and-sources/Chrome%20Inner%20Pages/03-Settings/notes/remove-inlineEditing#%2F07-LAI-languages.png%3Fz=width

We already had subpage editing for language detail, but removed it because it was weird having a subpage with 1-2 checkboxes. We want to add it back now?

michaelpg@: no, there is no consensus about moving inline UIs yet.  starting on this bug without consensus is a possible waste of your time.

#9: i already wrote the code for the demo in #5 (it's just a setTimeout). https://codereview.chromium.org/2627973008/

I just wouldn't recommend making the "detail" sub-page until we have consensus (and approved mocks).

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/c5bbdca617d68284f396f83f6294179cff4d8854

commit c5bbdca617d68284f396f83f6294179cff4d8854
Author: michaelpg <michaelpg@chromium.org>
Date: Wed Jan 18 02:59:37 2017

Language settings: Wait 100ms to close language action menu on checkbox change

Provide feedback to the user by keeping the language detail menu open briefly
when the user toggles a checkbox inside the menu.

BUG= 654964 
R=dschuyler@chromium.org
CQ_INCLUDE_TRYBOTS=master.tryserver.chromium.linux:closure_compilation

Review-Url: https://codereview.chromium.org/2627973008
Cr-Commit-Position: refs/heads/master@{#444254}

[modify] https://crrev.com/c5bbdca617d68284f396f83f6294179cff4d8854/chrome/browser/resources/settings/languages_page/languages_page.js
[modify] https://crrev.com/c5bbdca617d68284f396f83f6294179cff4d8854/chrome/test/data/webui/settings/languages_page_browsertest.js

it's not as bad now. future UI improvements should be tracked in their own bugs once UX makes the relevant decisions.