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Yes, anything can be done outside. But, it is much easier to work inside on a dry sled. You don't have to worry about dropping bolts in the snow!

You will have to check and see if the new slide will fit through the track window first for Dan's method. Some of those older Ski Doo's had small windows and this trick would not work. We always had to pull the skid out of the sled to change the slides. The slides were snug on the rail and we would have to tap them off and on with a rubber mallet.

Check and see if there is any plastic left on the bottom of the slide. That looks like the side portion in your hand. If there is some left, then going slow to the garage will work.
 

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When they are on the rail, they curve over time. This is normal. As posted, you need to remove the bolt at the front of the rail and drive the old one off the rail. Then slide the new one on. You will have to hit the end of the slider with a rubber or dead blow hammer to get it over the curve on the front of the rail.
 
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