<prompt> Human: Shortly after starting out as a computer repair guy 1099 back in the mid 2000s, I went off the rails. Addiction, divorce, homelessness, no record keeping and no filing of taxes. I think I was in some sort of payment plan with the IRS in 08, when I hit the bottle hard and started to live a blurry life. All my income from then until now was 1099, not W2, so while I never made bank, Im pretty sure I owe.Ive recently a few months ago sobered up. If I can keep straight, Id like to take my lumps and re-enter the system if I can do it without going to jail. Is there a way to do this?If so, I would like to use the GI Bill benefits I never used to go to school and learn some sort of trade. Would my tax situation interfere with this?I know Ive screwed up and Id like to make it right, but I just cant volunteer for prison. Is there another way?Thanks to anyone who can point me in the right direction.Assistant: GI Bill income is not subject to taxes, and the only requirement be that you still qualify for it, you get certified by the school you attend, and you get passing grades. It is not like VA disability, in that the GOVT can take your VA Disability if you owe money.As far as your other question, you need to talk to a tax lawyer ASAP. They would be able to give you the best answer to your question about re-entering the system.Human: I have to dig in and see if I still qualify for the GI Bill program. I remember I paid 100 per month into the program for a year while I was active duty, but I dont remember if there was a deadline for using it. Thanks for your reply. Assistant: There is a deadline. You are probably under the montgomery GI Bill. When was your ETS date month and year?Q: How long do I have to use my benefits?A: Once you have separated from the service you have 15 years to use your Post-911 GI Bill benefits and 10 years to use your Montgomery GI Bill benefits. Although separating from service starts the clock on your time limit, you should know that if you rejoin active-duty service for more than 90 days your eligibility clock is reset. In other words, you get 15 or 10 years from your last discharge.Human: I was honorably discharged from active duty in 1990 and from USAR in 1994. Looks like I missed the 10 year window. Thanks for your reply.Assistant: You can also rejoin for 90 days to reset the clock. Human: I didnt realize that was even possible. Do you have a link or any other info for this program? Thanks!Edit: look like I would have had to do this while still in the 10 year window. Ive missed it.  <response>: You cant just go rejoin the military. Budget cuts have made it a lot harder to reenlist, much less get back in. Youve missed the boat on the gi bill. 