When a user arrives to the "add/upgrade" plan section coming from them "Install plugin" link, they should only be offered a Business or Ecommerce plan.
I expected to be offered only the plan I need to install plugins, taking into account where I was coming from.
I was offered a lower plan which will not let me install plugins and, if I try again, I will probably be asked a further payment, causing quite a but of frustration and confusion.
MacOS 10.13.6 (17G2307)
Google Chrome 79.0.3945.88

This is somewhat related to this other issue https://github.com/Automattic/wp-calypso/issues/15671
Hmm, I think this nudge is meant to send you directly to the Checkout.
But this is still an issue with other nudges where you're not redirected directly to the Checkout. I'll open a PR soon. :)
PR in #41044 for this issue. :)
Seems this was regressed in #41002. #41115 should have fixed it.