Hello, I wanted to follow up on the question that a user posted in an old thread. I'm having an identical problem and wanted to see if any resolution was found. The thread is here. https://forum.parallels.com/threads/shift-key-temporary-ortho-mode-autocad-2016-windows-10.329191/ And makes mention report ID # 71847396 I have been in touch with AutoDesk support and have found they have suggested the following work arounds. However, because I normally use this AutoCAD on my Windows desktop, and this shift/ortho issue is one of the most basic and commonly used functions, I would really prefer it to have the exact same functionality I am used to on a my full Windows desktop. This article suggests creating a keyboard shortcut in Parallels that will work instead of SHIFT. (It incorrectly notes that this is an AutoCAD bug - it is not, since this works properly in a supportedWindows environment. There was a known issue with the Mac version of AutoCAD, but it has been fixed.) This article describes how to get the function keys working properly within Parallels. It also looks like other users have reported this issue to Parallels. It may be a good idea to contact them directly to see if they've fixed the issue or found a workaround for it. Thanks!