how to get voice alerts to work on nuvi2589 using a MacBook pro

Try following the instructions here http://www.poi-factory.com/node/25730 although it may be best if you explain what you want these 'voice files' for?

The nuvi 2589 lmt comes with Foursquare poi's. I am trying to get a .wav audio file to play when I get near these that are already on the gps.
I downloaded some wav files from here and used POI installer to put them on my SD card. They will not upload to the card.
I downloaded the list of rest areas from here an the wav voice file, but the only thing that plays when I approach the rest area is a beep alert not the voice alert.
No joy here. I must be doing something wrong.
Any help appreciated.

Custom .wav alerts only play on custom POI files (.csv or .gpx) that are loaded with POI Loader. They do not play on Foursquare poi's or on the built-in poi's included with the map data.

Here is a video on setting up custom POIs with WAV files https://m.youtube.com/watch?v=Fhhb5FPyLW0 see if that helps. Other videos that may help. http://www.poi-factory.com/node/45601

Note. Mac users have reported that the sox.exe is not required as a part of the process for the Mac's to get voice alerts.

This is very helpful.

Thank you very much.
After reviewing your videos I got it to work great.
One more question, can you change the icons on the built in poi’?
I uploaded some icons likc MacDonalds and Arbys but the did not show on my maps.
I guess they only work when you add custom poi’s. Thanks again for your info.

No you can't change the icons for the built in poi's. Check this out for icons pay close attention to "To enable the Up Ahead Places map layer" https://support.garmin.com/faqSearch/en-US/faq/content/BCnvn...

You can edit and changed the icons for favorites or saved places.You are limited to the built in icons. http://www.poi-factory.com/node/40052

One other note by Garmin. Although POI icons will be visible in all three map views, the zoom level will only be shown in the North Up and Track Up views.