Cautionary Tale (and I knew better) - Always Have a Second Key
Symptoms were initially intermittent functionality of Keyless Go to lock/unlock the vehicle doors. That progressed to the Keyless Go start button for the ignition going inoperative (within only a day or so of the prior symptom) via the "Key Not Detected" warning on the dash, but we could still start the car in the key slot with the smart key fob. That then progressed within only 24 hours with the key no longer being detected or recognized by the car whatsoever.
After troubleshooting the key battery (first thing I tried), it became increasingly clear that our key fob had "bricked" itself either due to a bad board circuitry, antenna module or otherwise (I'll never know as I'm not handy enough to troubleshoot). I also attempted new battery replacement (both the primary and aux) in the off chance the key wasn't the problem.
If this happens, your only solution is to have the vehicle towed to your Mercedes dealer so that they can then open a ticket to order a "First Key," which is more expensive than a "Second" or replacement key (where you already have the primary key in hand that is working with the vehicle). The First Key ships from Mercedes Germany. I worked with Mercedes of Chantilly and they made quick work to get the keys ordered and programmed and all in all from the time I dropped my vehicle to the time I picked up my vehicle it was about 6 business days, which honestly isn't that bad. The total bill came to ~$1,100 for a first and backup key + programming. So an expensive mistake.
And before you say "well yeah, that's your fault," I totally recognize it is, but also wanted to pass along this experience as I had not dealt with it before and if this saves one forum member the hassle and money by causing them to pre-emptively buy that secon/backup key, I've accomplished my goal with this post.
Don't beat yourself up - these keys are absurdly marked up and not always the highest item on your priority list. $1100 for 2 keys sounds about right.
Now I just need to order an extra key for the Hyundai that we bought for my 16 year old...




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