We have been doing some work recently on the picker popup so maybe something has stopped working as expected. I added a feature where when inserting an image into your page it would automatically fill out the ALT text for you from the asset's description, but maybe this has done something odd with making links to documents.
Thanks for reporting it. I'll look into it and let you know when it's fixed.
SVH_Webmin - yes you're right that Voice is quite old, but it isn't obsolete or abandoned. We're actively looking for investment into the platform to improve it and sustain it long term. We are keen to make it as WCAG compliant as we can!
Joe - Voice Admin