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Not all screen readers speak the <legend> text for each input in the <fieldset>, NVDA speaks it only once for each group when entering the <fieldset>, same with TalkBack/Firefox. VoiceOver OS X speaks it once for each input in the group only if you're TABing but if you're using VO+arrow keys or VO+CMD+J it does not speak the <legend> for each input. VoiceOver iOS does not speak the legend for any of the inputs, the legend is simply static text. JAWS speaks the <legend> for each input in the <fieldset>. This behavior could change as it has in VoiceOver over the years.
This behaves just like the default visible legend for a screen reader user when TABing through each input. Screen reader users can now also use heading element quick navigation commands.