I know that the ideal state would be to use positive connotation for checkbox labels as in
[✔️] do this
rather than
[✔️] don't do this
The system I am working on has many checkboxes in many different areas. Some of them with the ideal (positive) caption, most of them unfortunately with the not so ideal (negative) caption.
This has the following reason: In the past large sets of data were affected and all checkboxes which were implemented later either deactivated or at limited that data set. For example:
All images and their entire meta data are indexed.
[✔️] Don't index gps data
[✔️] Don't index caption date
Every time I bump in to a checkbox with negative caption a little kitten dies... It would be possible to negate all checkboxes and their states within the entire system. But I'm positive that
a) this would confuse existing power users and b) this would be technically quite time consuming
Shall we continue with this "system"? Shall we implement every checkbox with positive caption from now on? Should we negate all existing checkmark captions and states?
I'm not sure.
Answer
I would suggest that if a checkbox is used frequently and without little thought, either leave the label and its behavior unchanged or, if you do change it, make that change very prominent and easily noticeable. If the control looks the same at first glance apart from a slight text change, those regular users may not notice that the wording and the underlying logic has changed and will continue to rely on the same mental models and learnt behaviours.
If however a checkbox is buried away and used infrequently, perhaps in a settings or configuration interface, go ahead and change the label to use positive phrasing. Experienced users are less likely to have strict mental models about these areas and are more likely to pay attention to the labels when they do.
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