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I saw that you started to implement PEP585 support in mypy with python#9564 and you mentioned having some difficulties with the tests. Since I'm looking forward to mypy supporting it, I though I could help by writing them. Mostly I extended upon those already written for python#7963. If you want, you can copy my changes or merge this PR into your branch. Thanks for all the work you've already put into it 👍
If you have any questions let me know.