When selecting a task, pressing "p" to get the planning window, writing "now" only sometimes gives a result of a selectable time of the current time to plan the current task.

Other times as in the image attached, the planning window will be empty. Second attached image is showing the working case when there is a selectable item in the planning window which will move the task to "now" in the calendar, when selected.

When this happens it seems the sneak peek window to the side will show the previously shown time e.g. in the example it's a task that is already planned to "now", but if it's a task from the inbox I've seen that it shows 1st of November in the sneak peek window when the planning window is empty in "now" search.

Don't know if this is happening with other planning types as well e.g. tomorrow or others, so might make sense to look into those as well.