The 25K loan scenario described is definitely a quid pro quo prohibited transaction. Yes, the likelihood of getting caught is very low. But why risk it? Also, the whole idea is moot. There are at least two ways to take money out of a Roth IRA or Roth 401K without penalty or risk of audit. You can't take out gains without penalty, but you can take out any contributions you have made to Roth accounts. Since this was "already taxed" money you can take it out of the account and use it for whatever you want. So, if you want to take 25K to "sink into a custom 82 Jeep Scrambler diesel conversion", as long as you have 25K or more in contributions, you can take it out without worry of audit or penalty or need to pay back the withdrawal. The other option, if one is willing to pay back the withdrawal,(and assuming it's a Roth 401K, which I prefer) is to do a participant loan. In the 25K scenario as long as the participant had at least 50K in the account they can make the loan to themselves and pay it back over time. There are just too many ways to do things legitimately. Don't risk your hard-earned savings on bad ideas.