You can't hold SHIFT before holding on one of transformation corners to keep the proportions, To make it work you have to already hold one of the corners THEN you have add SHIFT to make it keep proportions. Reproducible: Always Steps to Reproduce: 1. Hold SHIFT before click and holding one of transformation corners Actual Results: Transformation is not happening. Expected Results: It shouldn't matter whenever you hold shift before or after holding on one of transformation corners Windows 8
Same goes for rotation, basically every operation requires you to hold any of transformation squares before holding shift to snap to degrees.
Yes, this is a known limitation of our current tool system. We want to fix it, but it's unlikely to be fixed before the 2.8 release.
*** This bug has been marked as a duplicate of bug 317200 ***