Let's assume that your question/objective is how to use the Opening Tool (not the Window tool) to correctly insert a Window into your Walls.
Or how to accomplish the same thing, via dragging out the Block into/onto a Wall.
As Nikki alluded to previously or straight-out said, it seems to be a Workplane issue.
Do this, to experiment and get a sense of what's going on:
>Up at the top Menu bar, click on Workspace
>Near the bottom, turn on by clicking on it-- User Coordinate Icon
>Activate the Workplane by Entity Tool. It should be in your Local Menu, available by right-clicking; or again go up there to the Workspace Menu and click on Workplane and proceed through the expansion fly-outs to get to and click on "Workplane by Entity".
>Start clicking on stuff, including that tall Wall in Figure-2.
>Keep an eye on the User Coordinate Icon as it moves around and rotates.
Also-- It seems that-- in Figure-2, in that tall Wall-- you did not insert correctly. That is why it is not behaving as you wish.
Since you rotated that wall (Z-axis is now pointing east, it should be up), the bottom of that wall is actually on the west side.
Don't know what I mean?-- Insert the window opening Block again, but this time drag it onto the west (left, in your initial view that you shared with us) edge of that Wall.
Better yet-- Simply rotate that Wall back to where it's Z is pointing up. Then insert the window opening Block.
TurboCAD is not going to create the "block-out" opening in that Wall if you insert the Opening in one of its sides; you have to insert it via the bottom of the Wall (which, as I said, since you rotated the Wall about its Y axis, is now to the west).