On the contrary, my first instinct is always “pushing a button”
Why is this? to avoid having holes in the enclosure? wouldn’t the external wire be vulnerable
now #fuckpushing has a new meaning also 
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Harder to waterproof, connectors are “easy”. Also with cables, if you don’t make sure it’s water proof on the other end, for example, inside the motor, water will enter the enclosure from inside the wires over the months and years
Ok but then how are you supposed to connect the battery/esc to the motors? Transmit the energy wirelessly? 
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Epoxy the male end (with the pins, not the holes) of a connector through the enclosure.
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Why this?
Is this true for all wires?
Interested to learn otherwise, but I find it difficult to believe enough water will travel the 6" -12" from motor to VESC, between the copper strands and insulation, to cause problems inside the enclosure. Especially if your wiring orientation isn’t a downward angle from motor to enclosure (i.e. the common vertical wiring from motor). And if this is a real concern, a dab of silicone sealant / potting compound at the VESC end should close up a possible opening, assuming abrasion doesn’t cause a break somewhere else.
If we’re just talking inside a loose jacket, totally plausible.
Has anyone had this happen to them?
Edit:
May be worth considering wet rated wire, i.e. MTW wire
Don’t know if all but probably, its the capillary effect that makes the water go, each strand is round, so you have plenty of space for the water
If you just ride once in a while in the rain of some small puddle probably won’t happen, but if you are a madman (@b264) it can happen
In a board I never had this happen, but on more than one RC car
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Maybe obvious, but an important note nonetheless -
Unless your enclosure/deck geometry doesn’t allow for some reason (pre-drilled), your screws (and mounting holes) need to go OUTSIDE your enclosure gasket. Otherwise you’ve sealed your electronics up all tidy… and then drilled 10 nice new ingress points
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I’ve had that happen not just on esk8s but also the house I used to own, water entered the main breaker box in the basement, by coming in through the power wire, between the conductors and the insulation around the cable.
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I used corrosion x waterproof spray on my previous board. I highly recommend. Watch this:https://m.youtube.com/watch?v=s4z8QMgTEA4 I also put a decadent pack inside the enclosure and silicone caulking around it and the wire holes. I went through lots of water no problem.
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What was it? Drugs? Loose morals?
Those packs are nefarious…be careful.
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I tried this before and recommend avoiding it. It’s too runny, it smells really bad and doesn’t seem to work super well, IDK.
If I could find mine, i’d offer it for free; I’ll definitely never use it again. Probably a moot point as shipping would overpower the purchase price, and I have no idea where it is and I’ve moved since I last saw it.
YMMV
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So water can’t penetrate the enclosure.
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Really? The smell isn’t too bad. It’s a spray it’s exactly what I expected. I just followed what they did in the video. What matters is if it makes electronics waterproof. From the video it is amazing and from my experience I say yes too. Before I added the silicone, I went through water for about month with just corrosion x and some water had gone in (watermark turned red) but nothing got damaged. Then I added silicone.
So to confirm, you’re saying put this end enclosure side.
If so, I didn’t realise that the female had any holes that went through the connector. As such, do you have any fears of the exposed pins being an issue on the male connector?
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Yes, the male end. Exactly.
The male side has pins and not holes.
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Question for those with top mounted enclosure boxes (MTB) -
If you’re mounting the box to the deck with fasteners, how are you sealing the fastener holes in the enclosure?
It seems like ratchet straps, velcro, or fasteners are the usual mounting options. Neither of the first two seems permanent or resistant enough to movement without eventually coming loose, via crash, jump, or something else.
How are people sealing fastener holes?
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i use a combo of high strength velcro (a 6x4” patch) and these straps:
VELCRO https://www.amazon.com/dp/B00404NIA6/ref=cm_sw_r_cp_api_glt_fabc_Q0YTFBAHAPTB1WQ1DYNS
Down Strap,
i promise even in tight situations, the velcro can hold the board (17kg) on it’s own
with rhe straps, it has no chance of moving in a crash
i can upload footage i have if you want