Pressing the up arrow key while your selection is on the first child block of another block should navigate to the parent block. At some point this behavior seems to have been broken and no longer works properly in master. This was working properly in Gutenberg 7.0.0.
I suspect this issue may be related to #18780 and #18881.
master as of https://github.com/WordPress/gutenberg/commit/49dac29050c054056746cd861c0d2c2e2146d68aWhatever fixes it should add an e2e test.
Appears to have been introduced by #18379
Fix proposed at #19135.
Whatever fixes it should add an e2e test.
As noted in the description of #19135, we do have an end-to-end test which attempts to verify this behavior (source). However, because it relied on the DOM as the source of truth, and because the active element in the DOM _was_ correct (despite it showing the wrong block's toolbar), the tests would pass. In #19135, I've updated the test to assert against both the DOM and the block editor state.