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Originally Posted by Leeper
It seems the rubber boot is too small to carry any additional wires and I am having a tough time trying to figure out how to get into the cabin without having to take off the whole fender (I really prefer not to do that).
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Seems like I remember this same question a few month back. You've answered your own question and didn't realize it.

If the stock route is too tight for the wire(s) / size(s) chosen you have to run a second sealed path in the joor jamb. Or oversize the existing one (requires an oversize sealing conduit too).
I've seen such done many times. Any custom audio shop should be able to do it. Its an advanced skills task. The very fact that your asking how implies you should probably consider paying to have it done (no insult intended).
Depending on many specifics of wire size and available space for routing, removal of the fender to perform the task is well within the realm of possibility.
HTH!