answer:TL;DR – It depends, but probably. Rules vary a ton between plans. They’re always going to ask and there are some good, helpful, reasons for them to. There are also a few steps to getting a straight withdrawal from a 401k and generally you’ll need to identify why you want the money at some point. But not always. The helpful reasons to ask - There are withdrawals that are “exempt” from the tax penalties (and withholding), so they’ll usually ask to make sure you’re not going to be taxed without it being necessary. (IRS link) – It’s sometimes possible to take a loan from your 401k and pay it back, so they want to make sure people are aware of those options. There’s no withholding or tax penalties on a loan. And the steps (which are completely dependent on the plan rules for your particular plan) - Some plans don’t offer a way to get at your retirement money while still employed with the company that sponsors the plan, so that might be a good first question – Plans that do allow for withdrawals sometimes require you to take a loan first instead – Almost all plans consider withdrawals to be “hardship withdrawals” so require that you either need the money for reasons laid out in the plan rules or some other process to prove hardship. Whoever takes care of your account should be able to identify who makes a decision if there is one. – If you get a distribution/withdrawal, the IRS is notified and you get tax form at the end of the year, but no one else is involved as far as beneficiaries or things along those lines. If you don’t want to discuss your situation with the person on the phone, you can just request paperwork and a list of suitable reasons usually. They’ll send it without you needing to share too much there. The best first step is probably to give them a call and just ask questions until you know all your options.