My mom hasn’t filed taxes in nine years. Is it better to start with old taxes to catch up? Or should I start with newer ones where we can get a refund?

[Critter-3]

Depends ... if there will be carryforwards on the older returns that affect  the more recent returns then start with the older ones.  Was she even required to file those past tax years ?   If she has refunds coming to her then file the 2019 thru 2021 now.  Refunds on older years are forfeited but balance dues still need to be paid. 

[NCperson]

@marcgunnfamily - does she even need to file? what is here income level?  did she work or just receive social security and pension income? is she a dependent of someone else? did she receive the 3 stimulus payments? 

as stated above, assuming no carryforwards, the IRS is not going to refund anything from 2018 on back.  

just because she hasn't filed in 9 years doesn't mean she had a requirement to file. Not everyone needs to file.

need to hear more of the story here. 

[marcgunnfamily]

@NCperson 
We are working on 2013 taxes. I think that year at least She DID need to file. She has lots of medical expenses which used to reduce her taxable income a lot. She used to get refunds. Not sure now. 

she retired in 2014 and is now on pension and social security. she has several rental properties. 

[marcgunnfamily]

@Critter-3 

Because of her medical expenses, she assumes she will get a refund for the past three years taxes

[Critter-3]

I highly recommend you seek local professional assistance  due to the complicated returns and the age of the unfiled returns  so that any late filing penalties can be mitigated if needed.  

[SweetieJean]

Right, agree that pro helped is needed, especially since she has rental properties.

[xmasbaby0]

Understand this --- she cannot get tax refunds for any tax years earlier than 2019, but if she owes tax for any of the tax years in which she did not file, she still has to pay the tax due.   Any refunds from 2018 or earlier have been forfeited.   Tax "due" never goes away, and could be owed with penalties and interest.

You say that she thinks she will get refunds for the past several years because she had medical expenses.   Refunds come from paying in more tax than you owe.   Her medical expenses may not generate refunds.   it is very difficult to get a refund based on medical expenses.    Only the amount that is over 7.5% of your adjusted gross income can be used as a medical deduction.   If she has not paid tax or had tax withheld from any income, there is nothing from which to issue a refund.

You say that she receives Social Security.   Did she receive the stimulus checks?   Recipients of SS were supposed to receive those automatically, so she should have received the 1st one of $1200, the 2nd one of $600, and the 3rd one of $1400.   If she did not receive them, she can get them on tax returns for 2020 and 2021 by using the recovery rebate credit.

Software is available for the 2018 onward, but the online software is only for the current tax year of 2021.   Any earlier years must be prepared using download desktop software on a full PC or Mac.   Only a 2021 return can be e-filed.   Other years can only be filed by mail, which takes a very long time (6-9 months) to be processed.  Other years would have to be prepared by hand, using the paper forms.

You say she has been receiving Social Security and a pension, as well as rental income.   It would be better for her to seek help from a paid tax professional in your area.   She may need help in gathering together all of the records she will need to provide.    This does not sounds like a good do-it -yourself project.