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Almost a disastrous 1st trip (but it isn’t over)

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The OP said that he tried 4 different Superchargers and failed to get any of them to work. Granted, he's a new owner w/o experience, so it's not a huge red flag. But it's still not reassuring. Then another poster in this thread said that the trick to getting it to work it to push in the connector "quickly". This advice is far from intuitive or normal-sounding, so another worrying data point, IMO.
After over 56K miles and probably over 100 Supercharger sessions I have never had a problem connecting to a Supercharger stall and having charging start. I use no special "tricks".
 
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Wouldn't it still be a good idea to have your foot on the brake anyway in case someone rear ends you? Also, so your brake lights are on for traffic behind you? Unless the brake lights are on in that situation, I use creep so I don't know.

No. It actually doesn't matter, because "hill hold" keeps the brake lights on, as well as keeping the brakes locked. It shouldn't matter whether you use creep or not.
 
I drove my first Model S for 80,000 miles and have taken many long road trips. I can count the number of times I have had trouble getting a solid connection on the first try on one hand. On the other hand, I have had numerous problems plugging in my 6 year old LEAF using a ChaDeMo charger. This connector is very heavy and far more difficult to plug in. I would not worry about being able to use superchargers. There is a learning curve but it is not steep. As pointed out up thread, a child can do it.
 
When I first got my car I had a couple of instances where I din't get the charging connector in all of the way. I think the port was tighter in the beginning, or I figured out it that takes a little more force than I was expecting. I would think that you wouldn't have four fails with four attempts, but you never know. My guess is that there is something wrong with your cars charging system. Maybe just the charging port. I would take it to your service center and have it checked out before you go on your next road trip.
 
Update.... The good news is that we made it home without only a slight scare at Plymouth.
We stopped at the Plymouth charger but 20 mile rated spare get to Rocky Mount as our backup. 1st attempt to connect I got the dreaded Orange connection. My 2nd attempt I applied a little more force and held it in place longer and FINALLY got a good connection. It seems like this station just needs +20 seconds to fully connect.
When I 1st connected, I could hear the transformer relays click within 10 seconds like at the other 2 SC that I used. When I held it longer, I heard another relay click and that's when I got the Green connection. Rocky Mount and Burlington NC (previous weekend) took less than 15 seconds to make a good connection and it was more like 10.
It was also interesting that I was the only Tesla charging, and the SC only made it to 70kw of power during the charge and stayed around 65kw most of the charge. I have a software limited 60 and I was well below 80% of the 75kw battery during the charge and did not do a full charge. Rocky Mount hit a max of 93kw and stayed in the upper 80's. Same with Burlington. Both of these were full charge and I stayed in the upper 80's even to the end. I guess that Plymouth is just a lower powered station.
I didn't pay attention to the voltage level to see if that might be the difference. My work public charger and my home charger are both 30A (displayed on the screen and apps). My home always is at or slightly above 240v vs work typically around 225v, and I get 2 more miles/hour charge at home. Plymouth is a very rural area and our cell phones and the Tesla had extremely weak cell coverage over 5 miles of driving in that area.
While I am new to supercharging, I have 3 years of experience connecting to various public chargers with our previous Volt, and never had issues or delays connecting. At least now I know that I may need to just the SC more time to connect and not give up as quick as I did the 1st time when the relays clicked. It is much higher volts & amps to deal with than a normal charger, and it seems like it just takes longer than what I was previous use to.
 
I'm a local here too - glad you made it! Been thinking about adding some 14-50 outlets to my rentals - I have one on the beach road where I could loan you my 50amp extension cord to plug into the ground level stove outlet should you need it: The Sea Witch

OBX John, I wish I read your post earlier. We were just up the road at the Comfort Inn. This was a last minute getaway trip but we will keep your place in mind. Our friends are also interested in off-season weekend getaways.
 
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OBX John, I wish I read your post earlier. We were just up the road at the Comfort Inn. This was a last minute getaway trip but we will keep your place in mind. Our friends are also interested in off-season weekend getaways.

Sounds good - I have two vacation rentals here, and about to turn my old house into one and it already has a Tesla charger, so let me know if you plan to return!

That's strange the Plymouth supercharger is acting up - it actually charged my MS faster than the Rocky Mount station on my way home from picking it up in Raleigh. I'll make sure I leave the beach with a full charge if I head that way!
 
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After over 56K miles and probably over 100 Supercharger sessions I have never had a problem connecting to a Supercharger stall and having charging start. I use no special "tricks".

Just returned from a 2700 mile trip in my MS60(Cape Cod to Orlando and back) and never had a problem or used any "tricks". For those who don't have a Tesla, this process is as simple as "round peg into round hole" and that's it.

With that said, I recently helped a newbie with their first charge at our local SC on a freezing cold day. It was so cold the charger required a little extra pressure in make the connection(plastic gets a little "sticky" when super cold).
 
I'm a new owner ...

There are many things different about MS than an ICE car that take time to get used to. I still find myself holding the brake pedal while at a stop sign even though Creep Mode is turned off.
I've had mine about 6 months. I've had creep mode turned off the whole time... and I let the car just glide in, w/o brakes for the final 3 car lengths. Takes about 30 seconds to do it too, heh!
 
Never had anything but white/blue/green. I'm interested in these other colors for my chargport but they seem to be less desirable....

The Tesla Model S charging port is a bit harder to plug into than the LEAF which is super easy.
 
Same here.
Except when I did have charging problems, it was user error and I didn't insert the plug all the way or not enough force.
This was my experience, too. Early in my ownership (about 10 months ago), I had some problem to get the SC at Auburn to work. I moved the car to a different SC plug, and it worked the second time. I called Tesla service to advise them that maybe one of the SC units was having a problem; they looked on their network monitor and could not see one of the units being down (they monitor these); so I concluded that when I plugged, I didn't push hard enough. Since then I have not had a problem with the numerous SCs I have used.

Sometimes it just takes a little practice and patience. Regarding the charging plug itself - it appears that the contacts (both male and female) are silver-plated. This is good, because silver is unusual in that even when tarnished, it still conducts very well, because silver oxide is conductive. When people use their cotton swabs and other things for cleaning, I guess they are cleaning off dust and thin coatings of other contaminants; alcohol and contact cleaner will not remove silver oxide (but this doesn't matter due to its good conductivity).