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I am bit confused while showing help text in a lengthy form. Please refer to the image for below query:

Where we can show user initiated static help (left side of the mock):

  1. How to show help icon for radio buttons placed horizontally? If its placed right to last radio button, won't that mean that its just related to last radio button? (which is not the case)?
  2. Same problem exists if radio button placed vertically.
  3. Where to show the help icon if drop down has optional fields (help text cover details with respect to that as well)?

Where we can show dynamic help (right side of the mock):

  1. This help text is hidden unless user interacts with the radio buttons. But even in this case, when to show it and where to point the help box?
  2. same problem exists with radio buttons placed vertically, If I point it for any of the radio buttons, it will look like its meant for that only.
  3. This becomes more problematic when it comes to drop down with additional optional field. When to show the help and where is the question?

What needs to be done in these cases? Whether to go for user initiated (static) or dynamic help will depend partly on these issues in my case.

enter image description here

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I would rarely recommend "dynamic help", if I understand your explanation correctly: Popping up additional information on every field while the user goes through the form will likely create so much noise that the user is distracted from his main task (filling in the form).

A use case where "dynamic help" might be of help is very low frequency (once a year) and where labels cannot be translated into user terminology. My tax statement comes to my mind. But from a design perspective, at this point I'd try to eliminate this UI entirely (which of course only works for my tax statement if I pay a consultant to do it - what I actually do).

Aside from these, there is the issue that a radio button or a checkbox only gets focus if you click it (as long as you don't use TAB). So the user must make a choice to get information on which choice he should make - wrong sequence. Finally, I've never seen this, so it is likely to be uncommon and thus surprising to your users.

Regarding placement of "user-initiated help", you have a point here. I do not think it is very serious, though: Even if the user thinks only one radio button option is explained, and he is looking for an explanation of the entire radio button choice, it's near enough to be found, and once visible, the explanation should make it clear it's about all choices. Regardless of vertical or horizontal layout of the radio button options, I'd put the (i) in the row of the label, to the right of the radio buttons (so one row higher than your vertical example).

For the DDLB with "optional text field" (which needs not be optional, so your term is a little confusing), the placement is clear, I think: To the right of the DDLB, if the help explains the choices in the drop-down box, and to the right of the input field, if the help describes which values go into the input field.

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