If you can provide those kinds of affordances to someone after they've informed you that they're "struggling, either professionally or personally", then you can do it without making them have that conversation as a precondition to your charity.

If someone is struggling, that means they're vulnerable. Forcing them to take a gamble by enlarging the "surface area" of the risk that they're exposed to (by advertising it to someone else) is shitty. It punishes people who can't take that risk (in other words, the people most in need of relief) and also (separately, possibly doubly) punishes the people who manage to successfully cover their own bases without slipping or otherwise indicating that any of this is coming at great cost.

Corollary: you should assume that anyone could be struggling at any time (or all the time), and default to giving everyone whatever latitude they've earned and deserve, whether they've had an intimate heart-to-heart with you beforehand or not.