I’d move these when they are as young as possible, if you have a crop of seedlings. The digitalis are basically biennial (or a short-lived perennial), so the parent plant doesn’t exactly come back with a 100 percent guarantee.
Here I would be more inclined to let it sow babies from its seed and move those…
The Amsonia will soon take over the universe, sowing EVERYWHERE. It seeds like mad, but is hard to dig out, I find, even when small-ish, hence my advice to move young babies if you can when you see them.
With transplanting in general, hottest/driest summer is the worst (other than winter) so wait until September.