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@sboyd992 Could you make a screenshot of the situation and may be tell a little bit more of the place of this room? It can happen that when the room is on top of another one not every room will be tiled.
For instance when there are other room boundaries and ceilings beneath it.
Instead of using the shift click option you can also use the option I marked in the red square on the screenshot.
When that doesn't work for you please let us know.
Have fun playing. 😉
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