I have shed a grad student.
A person with lots of enthusiasm and a great idea for a thesis, but who struggled with writing and organization. A person who could not meet deadlines and who dropped out of contact for months on end. A person who spent a year learning an obscure language in order to be able to work with the required sources. A person whose personal life seemed to be a neverending series of crises, probably all quite real and serious, but all of which coincided with work deadlines.
I tried structure. I tried letting go and waiting. I mixed and remixed compassion and strict guidance. I sent a long, kind e-mail telling this student that a graceful exit was okay, and had no reflection on them as a person; that it was okay to admit they'd gotten in over their head; that there was no judgment. Finish if you can, but get out if you need to; there's no need to punish yourself. All to no avail. Even the impending seven-year up-or-out deadline (set by the university) had, in the end, no effect. There were apologies, and professions of really wanting to finish, but...
And now this student has realized this, just as s/he has run out of time. Yesterday, with my concurrence, the grad director sent a kind but firm "no" to a request for another extension. And I know that's the right thing to do. But I still feel rotten.