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How do I redirect water to the gutter (as intended) and not behind the siding? Water is currently leaking behind the siding and exiting just below the gutter end cap. Gutter is clear, gutter pitch is good and gutter end cap seams are fully caulked.

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This isn't really a matter of siding, but of flashing. Siding (especially vinyl) is poor at this job.

You want a kick flashing, like this. It should be installed first, then the siding added around it.

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source

Here's how it might look with vinyl. Note the extra piece of vinyl cut to flash over the kick:

kick flashing vinyl example

And an option with full channel:

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Here's a good guide to step and kick flashing provided by Edward.

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    Thanks. So really a question of the j-channel, as this is an insufficient method of keeping the water from this location. In reviewing these instructions, the kicker flashing should install all the way up along the wall. hammerandhand.com/best-practices/manual/6-roofs/…
    – Edward
    Jul 26, 2023 at 16:09
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    I pulled the caulk from below the end-cap as well and can see to the backer board, which is soft and rotted of course. Sigh. This issue is bigger than the kicker, but the kicker needs to be installed as part of the fix. Thanks for your help.
    – Edward
    Jul 26, 2023 at 16:13
  • Not exactly. "Step flashing" needs to be interleaved with each row of shingles all the way up the slope to work properly. The kicker is just the bottom bit.
    – isherwood
    Jul 26, 2023 at 16:13
  • Yeah, not a pleasant discovery. I'd look into a vinyl removal tool and plan to peel it all back from that area. It's not as painful as it sounds, though.
    – isherwood
    Jul 26, 2023 at 16:16
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    Found one that reflects how I've seen it installed before. They use a diagonal cut and an extra overlap in the siding, which I don't hate. Swapping it in now.
    – KMJ
    Jul 26, 2023 at 19:03

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