I've tried to play with Smalltalk on my vacation and I've had some troubles with Squeak and Pharo.

Surprisingly, everything worked out of the box with Cuis and its vector graphics rendering makes the experience much more pleasant. I'm impressed!

For the record, on my Linux box, Squeak would have troubles with my keyboard input (I can't type a caret!) and Pharo had DPI scaling issues where everything becomes blurry, as well as some crashes here and there.