Dear John,
Since I last waited for a response from Microsoft Answers, I have invited my MS Guru buddies over to troubleshoot this problem. This is what we determined:
- the touchscreen area within the boundary of the square box 🗒 is too tiny for a simple finger touch to land in that space. The touch is instead connecting somewhere around the square which in turn causes the selection action not to work as expected. Microsoft will need to correct this in the manner consistent with their business and technology plans.
- In the meantime, we have found that a functioning Surface Pen correctly selects the boxes each time, since the end of the Pen is smaller than the checkbox boundary. This would be an adequate solution if every Surface were shipped with a Pen. I don't think they are. I paid extra for mine.
Until Microsoft addresses this issue, the Pen is the best way to consistently select the checkboxes. Of course this would be true for a keyboard or mouse add on as well.
Hope this helps your readers!
You're Welcome,
V and the ad hoc troubleshooting team.