If a guide is ctrl/cmd-dragged while a transform is in process, the guide creation is not added to History.
1. Create new document
2. Use marquee tool to select an area of the canvas
3. Select Free Transform
4. Ctrl/cmd-drag a guide onto the canvas
5. Enter a rotation value
6. Apply the transform
Result- transform is applied, new guide is added, guide creation not in history (see attached video)
Windows 10 Pro, PS 22.5.3