Problem Building Dormers

@TiggerIsMyCat24 I'm so sorry but I cannot seem to reproduce the issue on my computer. Is it possible for you to upload your lot to the gallery with a name something like 'Dormer Error', then let me know, plus let me know if your name is different in the gallery? This way I can download and test it in my game. Thank you!

@TiggerIsMyCat24 

What is the squiggly line in the floor in the left dormer location?  It looks like it may be the top of a curtain below protruding up.  Try removing that to see if it helps.

You can also use the point to point wall tool and go around the entire space that includes the dormers.  Basically redraw all the walls.

Another thing you can do is rather than use a large roof, try using separate roof segments around the problem dormer.

Also, if you have any fences (I don't see any) roofs and fences can be a pain and do what you show in the 3rd picture.  

And sometimes a lower roof intruding into a room like that will fix itself if you apply a room to the dormer.

I don't know if any of these will work but it might be worth a try.

You need to move the bay window or the dormer, I think the bay window is interfering with the dormer, another way is to remove the roof and floor for that room only you can always add it back, also that is not a complete room complete rooms would fix the dormer problem.  you need a wall on that one side, than the roof will disappear in that area.

@TiggerIsMyCat24 Wow. I may be wrong about this, but it's been bothering me that I couldn't reproduce the issue to test it in my game, then I realized something. I feel like I missed the elephant in the room... Please check this video that I made and see if it covers what's happening in your lot.  I was bothered especially by:

1. That you said on the one side that does clip you hear/see the 'thunk' when drawing walls, but not on the other side that does not clip, and...
2. I see that on both sides your dormer window 'small rooms' do not have a ceiling. 

Several things perplexed me in your pictures, but those two were key in my end hypothesis... I'm wondering if part of the wall(s) in your room are created by the roof rather than by the wall tool. I'm guessing that something in the method you used caused the missing ceilings in those areas, but it seems that at some point your area on one side did become seen by the game as a room (thus why you see/hear the 'thunk'), bot not on the other side.

You could re-trace all areas and make sure they are sealed rooms (as @CGrant56 mentioned). Select the side of each room and go up a floor and click the yellow rim to create ceiling also. I think that doing both of these things may solve the issue. Please check the video out to see what I mean: https://youtu.be/dY8mBwnEqNA