Send address to the car?
 

It always fails for me as well through Mercedes me. However, I just stopped using the Mercedes navigation system and instead just use WAZE or Google Maps. Only bad thing is you can't see the directions on the HUD.

this has been discussed in several threads already.

sending addresses is a hit & miss.

it definitely won't work when the car is not connected (underground parking) at the time the address was sent.

i'm not 100% sure, but time seems to be a factor as well.
the longer you wait between sending & getting in the car, the bigger the chance the address is lost.

what always seems to work is when you are in the car & then send.. but that defeats the purpose of course.

what ALWAYS worked was sending an address through the Mercedes me WEBSITE.

the address would be stored on a server which you could then call up in the POI app in the car. (you could make a list of addresses)

the POI app is still there in the car, but you can no longer send anything to it via the website ( (but on it, the feature is still described).
I've raised the question with Mercedes but so far have not got any constructive feedback as to why this feature is gone

I have had it work, when I use the iPhone Mercedes me app. In send to Benz, there is a space to input an address or use a connection address. When I select navigation in the car a screen appears that tells me the address was stored in previous destinations and do I want to navigate to it now.

I'm in the same boat you're in. It worked when I first got the app, but now it just does what yours shows. Says it was sent, when in reality it never pops up on the screen. Doesn't matter if I send it in the car or outside. Wish I could find a solution. Opened a complaint file with MB app.