Repro Steps:

1) Create a Page
2) Introduce a Button to the Page, and size it to 512x256.
3) Select the Button, and in its Transform Properties, set its Properties to be: Angle=30, SkewAngleX=30
4) Right-Click on the Button, and from the Templates section, select 'Create'. This will open the Template in the Template Dummy Editor.
5) Right-Click on the Button's default Root Border, and from the Context menu, navigate to Layout-->Replace With-->Grid
6) Select the newly-formed Grid, which will expose its Grid Definition Adorners.

Observe how the Adorners are skewed. In my mind, this is correct behaviour.

7) Right-Click on the '*' (star) unit of Measurement within the Adorner.

Observe how the Context-Menu displays at an angle.

Expected Results: Application Context Menus are always 'flat' in all circumstanced.