A few quotes from the Rabbi on 'Tzedakah and Healing'
in which he instructs to be more compassionate towards orphans and widows than towards others
A person must be thoughtful of orphans and widows even if they happen to be wealthy. It is an outright transgression to mock them or cause them any anger or sorrow, and all the more so to curse them. It is, however, permissible to be persevering with them in what concerns teaching them Torah, craft or the right path. Mocking, angering or cursing any Jewish person is a transgression, but doing so to orphans or widows counts as two transgressions. In any case, one is not to treat them as one might anyone else, but one is to differentiate and act with great compassion, whether the orphan has lost his or her mother or father. The saying that "orphan" refers only the loss of a mother… actually means that the loss of a mother is more obvious that the loss of a father. How long are we, on this matter, to consider someone to be an orphan? Until the person does not require support from others and can take care of themselves, as do adults.
Mizmor Le'Assaf, Ethics for Sunday, p. 128b, Livorno, 1864