For the sake of any newcomers to this thread, I ordered a new key fob for my '99 E300D. After going through a vigorous search for a dealer that wouldn't take me for a ride and steal some of my money, I found a dealer at ome distance that was not going to charge me for a programming fee.
I plunked down close to $250 and in 3 or 4 days they called and said my key was ready to be picked up.
I drove down and got my nice beautiful new key fob and thought what a nice deed I had done, my wife could use the new fancy key fob with its chrome logo on glossy black background with a panic button and all. I kept the old original key, a flat leather like thing that showed significant wear and I was afraid if it failed or got lost I would be in a really bad place if I didn't have a backup key.
Then the KEY FROM HELL made its way into my life.
the new key flaked on me a few days later, I stuck it in and after the glow lite extinguished I turned it to the start position - and NOTHING! switched back to pos 1 then repeated the sequence - NADA!
Removed the key from the EIS reinserted it and voila! it started!
My first reasoning was like maybe the EIS had to get to know the serial string transmitted by the new key? something technical like that might explain why it was stubborn like it was.
The key worked fine for a week of intermittent use, I actually went to using the old key and my wife used the new one, then crimeee! she comes home telling me how the key would not start the car at the supermarket and she was about to call me to come get her when she tried it a third time and it started the car.
I had a friend who had never driven a Mercedes diesel and he is into racing cars (was/is a referee at some events) so I drove some 100+ miles and stopped by to see him and asked if he wanted to drive a nice 20 year old diesel car with less than 50K miles on it. My ulterior motive was he knew his way around the town where he lives and we were going to find a place for lunch so I let him be my chauffeur. Well, it worked but when we got to where we were going he couldn't remove the key from the EIS. I thought one had to be sure the transmission was in park, etc and pressing the brake pedal, anyhow it was a ***** to turn all the way left (CCW) and yank on the key and it came out.
I decided it was time to exercise the 2 year warranty on the key so I drove down to the dealer I bought it from and the parts counter man told me he had not seen a bad key before but he tested the battery and it was fine so he introduced me to the service dept receptionist who wanted to make an appointment for me to drop the car off.
Before hand I understood the dealers might need to verify the EIS was working and if not they would charge me more than what the car was worth to replace it.
Not being a novice with these matters, I didn't let on that I knew a lot about how dealers make money - lots of it - off dumb car owners. I made an appointment for 10:20 the coming Friday.
On Friday I arrived at 10:15 and discovered a long trail of parked cars at the side entrance where the big SERVICE sign is located.
There was at least a dozen cars, all of them much newer than my 20 year old diesel, but the center lane was open and there was a parked SUV at the end.
Someone motioned for me to drive down and shut off my engine.
A Sprinter came in and parked behind me.
I will chronicle the series of events that followed.
While waiting there with nobody around I was thinking how dumb to schedule appointments to drop off a car in 5 or 10 minute increments. I had a dentist that did that trick and I still had to wait a half hour to be called in for whatever.
A service rep came out to the Sprinter and they start talking about something, he raised the hood, blah blah blah so I switched on my CD and listened to some music.
10:25 a service rep comes over and wanted to know the name of my rep and I said it was so and so and I had a 10:20 appt. He said my rep was helping someone behind me

The rep disappears with the driver of the Sprinter to inside the bldg.
10:32 my service rep came over and introduced himself and in the same breath asked why I was here (don't they print out some kind of service document?) and I told him basically the key from Hell was intermittently disfunctional. The he asked if I bought it there at the dealership (WTF man, yes

I produced the sales receipt and he asked me to let him try it. I had been using the old key so I stepped out and gave him the "bad" key. He tried it, it worked. He tried it again and I noted he failed to wait for the glow light to go out. Probably unaware my car had a diesel engine
4 maybe 5 times it started then AHA! after the last start he went to remove the key and it was stuck!
I said let me try it, I got in pushed the brake peal turned the key hard CCW and yanked and it come out.
Now remember what I was saying about the EIS issue? He said "well, you have a bad EIS" and then I broke into his canned dialog about how it was going to have to analyzed and before he said it was going to cost me $1500 plus labor I said hold on here and tell me why the old key works 100%, its never failed it ALWAYS starts and it NEVER sticks in the EIS and I wasn't going with his diagnosis.
He said well OK, it might take a few hours for their technician to analyze the key on their "reader" and I said fine I will just hang out inside while they checked it over and BTW I needed the car by 1:30 drop dead in order to keep another appointment 40 miles away. I sorta wondered if he was going to offer a loaner car, but no such luck.
10:53 he drives the car off and I went in and found a nice comfy chair away from the big screen TV that other customers were watching. I had brought some Italian Biscotti and grabbed a cup of their free fresh ground coffee and opened my laptop.
I watched as about a dozen service reps stationed in their desktops with a telephone and their smartfones in hand as they gabbed with each other. After the Sprint I saw only one other car arrive for service.
At some prearranged moment as if on-cue the reps began carrying their waste paper cans to a big plastic receptacle that had been wheeled out. In a short time it was nearly full. so much for the paperless office concept
11:50 my rep come over to let me know they were still checking it but it seems to be a bad key!
He said it will be a while longer though.
12:00 noon I got another cup of coffee and then noticed the reps - all twelve of them with only two exceptions - disappeared for lunch.
Now it was dead! a janitor came around to clean the swinging glass doors, blew some dust off the walkway into the driveway with a leaf blower than it got so quiet one could hear a pin drop.
A big black S55 pulled in and the driver walked in didn't find the service receptionist in (presumably at lunch) so he walked one way then the other until he found one of the older reps that decided to sit at their desk and watch their screens. Said he needed a battery, they said something I couldn't hear then he walked back out and sped off. Obviously not the time or place for a quick battery replacement.
I stopped keeping track of time but service reps started returning from lunch with a few of them so chatty I couldn't continue napping.
It was around 1:15 when the rep showed up and said yes the key was defective

He said it would be reordered under warranty but I could keep the old key until the new one arrives and they would call me when it was available some time next week.
I asked if it was coming from Houston and he said why yes how did you know that? I said something like I wasn't born yesterday I had been buying keys from Mercedes for over 25 years and I knew they made them in Houston.
Feeling like I was inflated again after the near 3 hour ordeal at least they didn't mention anything about the EIS again. I was prepared to ask for the manager to escalate my case if they said I needed an EIS.
If anyone ever experiences this type of issue with a new key ordered from a dealer I hope they read this. And I hope their wait time is not as long as mine.
I will post the outcome of the new key and hopefully its fine, if not then I will be here to let you know....
DDH