While you cannot place a wooden ladder on one side of a roof (no intersecting with the roof margin allowed), you can place the same ladder on the other side, as in those 2 pics.
https://files.facepunch.com/forum/upload/132559/151d8ef2-0b86-4bfa-b467-0e0b9a90215a/woodstair2.jpg
https://files.facepunch.com/forum/upload/132559/671c3444-faa7-4bb2-8204-43b097501757/woodstair1.jpg
Q is: intentional or loose end ?
In picture 1 (blue - allowed) the ladder is being placed on the wall, which is allowed. It sticks through to (and above) the roof, but that's just how it is. Middle of the ladder is what decides how and where it "clips".
In picture 2 (red - not allowed) the ladder is being placed on the roof (roof side of the wall), and since no placement on the roof is allowed, its of course shown in red.
If you want to place it in pic 2 - you have to drop it lower, so that it clips onto the wall thats in the building block below it.
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