Arrrghhh ! Just taken me 5 tries to get that little bugger on, it defies belief that all those high powered engineers couldn't come up with something better, or guess what, just use a standard power jack or even make it out of plastic like the pen so it doesn't scratch the cr@p out of the surface. . How much do these people get paid to come up with such ingenious ways to mess such a simple thing up. Aaarrggh !
Rant over heh heh heh
It requires patience, calm and being polite with your device and power adapter. If you are a jerk with the plug, it will be in the mood of not being helpful and refuse to go in.
Go on a date and hug your power adapter will greatly help. Although, kissing it might result in shocking results, so perhaps best not to do that. I am no expert, but don't think it will make a Surface Mini a reality going further in the relationship
In all seriousness, what I do is position the device in laptop mode, and connect the power connector from the top.
They did fix it in the Surface Pro 3. The connector is longer, and in triangle shape, making it easier to align, and it is in plastic so it won't scratch the device. Sadly, you can't use it on the Pro 2.
It is also longer.
The connector of the Surface Pro 1/2 works well, but not so much if you trying to avoid scratching the device all over the place. If you try a Macbook Air or the latest MacBook pro, the connector is even harder to connect, despite similar in design. But it not an issue, as you can allow the connector magnetically connect wrong and you have to slide it in, in place, as the body is in aluminum with no paint. So it won't scratch, well not show them.