Do this in the morning while both flowers are freshly open, since the receptive window is short.
Utah State University Extension guidance on vegetable pollination confirms that hand-pollination is most useful when female flowers are present but insect visits are unreliable.
The important limit to understand is that this technique cannot solve a situation where the plant is only producing male flowers during a heat episode, or where the underlying problem is disease, insect damage, root stress, or severe water stress.
Colorado State University Extension’s cucurbit guide reinforces that female
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