I haven't filed the last 2 years, but did file for extensions. How do I proceed from here and get back into filing regularly again?

[dlumarque]

subject sums it up. I'm feeling a little daunted by going through a bunch of old documents and also acquiring income statements from all the jobs I've had in the last year (a layoff caused me to pursue an assortment of seasonal and short term work).  Is it as simple as filing by this year's extension date and then filing last year's report afterward? Or should I submit the oldest tax report first before filing this year's? 

[xmasbaby0]

If you are getting refunds, you have three years to file and still receive the refunds.   If you owed tax due for 2023, even if you requested an extension you were supposed to pay your estimated tax due by April 15, 2024.  An extension for 2024 gives you until October 15, 2025---but you were supposed to pay estimated 2024 tax due by April 15, 2025.    At this point,   you need to just get the returns filed.    The 2023 return cannot be e-filed; e-filing is permanently closed for 2023.   Your 2024 return can be e-filed until October 15; after that, 2024 will also have to be filed by mail.

It is up to you to seek W-2's from the employers from whom you received income; or to get the 1099NEC's from clients for whom you worked as an independent contractor.

 Some employers have payroll sites that will have your W-2. You might need to phone, text, drop in, email and/or snail mail an old employer to make sure they know where to send your W-2.

https://ttlc.intuit.com/turbotax-support/en-us/help-article/tax-forms/get-copy-w-2/L8FTim9MO_US_en_U...

You can get a wage and income transcript from the IRS:  It will not show the actual W-2, 1099’s, etc, but will show the income information the IRS received.  It will not, however, show your state information. It will only show the federal information.

https://www.irs.gov/individuals/get-transcript

Other ways to get W-2’s:

Pay Social Security $62 per tax year for your W-2’s.:

https://faq.ssa.gov/en-US/Topic/article/KA-02501

[xmasbaby0]

You cannot change the tax year.   The current online program is for 2024 only.   Only a 2024 return can be prepared online and only a 2024 return can be e-filed.

Online preparation and e-filing for 2021, 2022, and  2023 is permanently closed.

Note:  The desktop software you need to prepare the prior year return must be installed/downloaded to a full PC or Mac.  It cannot be used on a mobile device.

To file a return for a prior tax year

 If you need to prepare a return for 2021, 2022, or 2023  you can purchase and download desktop software to do it, then print, sign,  and mail the return(s)

https://turbotax.intuit.com/personal-taxes/past-years-products/

You may also want to explore purchasing the software from various retailers such as Amazon, Costco, Best Buy, Walmart, Sam’s, etc.

Remember to prepare your state return as well—if you live in a state that has a state income tax.

https://ttlc.intuit.com/turbotax-support/en-us/help-article/state-taxes/contact-state-department-rev...

When you mail a tax return, you need to attach any documents showing tax withheld, such as your W-2’s or any 1099’s.  Use a mailing service that will track it, such as certified mail so you will know the IRS/state received the return.

Federal and state returns must be in separate envelopes and they are mailed to different addresses.  Read the mailing instructions that print with your tax return carefully so you mail them to the right addresses.

[FranklinF]

it is recommended to file the oldest tax return first. This is because information from an older return, such as a carry-forward loss or credit, can affect a subsequent year's tax return. 

Here is a breakdown of the steps for filing overdue taxes:

Step 1: Request an extension and gather income documents

• File an extension for the current year tax return when applicable. An extension gives you an additional six months to file, but not to pay. You can request an automatic extension by filing Form 4868 by the April deadline.
• Gather past income statements. You will need your income information, such as W-2s and 1099s, for all unfiled years.
  • Contact former employers or payers. This is often the quickest way to get copies of lost tax forms.
  • Request an IRS transcript. The IRS can provide a Wage and Income Transcript for the past 10 tax years, free of charge. You can order it online, by phone, or by mail. A transcript is not a copy of your return but contains the necessary information from your W-2s, 1099s, and 1098s. 

Step 2: Prepare and file past-due returns

• Complete each year's tax return individually, in chronological order. You must use the tax forms specific to each year you are filing. You can find prior-year forms and instructions on the IRS website.
• File by mail. You cannot e-file past-due tax returns for most years.
• Address penalties. If you owe a tax liability, you should pay as much as you can to reduce penalties and interest. The IRS may be able to offer penalty relief for reasonable causes, such as a layoff or personal circumstances. 

Step 3: File this year's return

• File before the extended deadline. Since you already filed an extension, you must submit your return by the new, extended due date to avoid failure-to-file penalties.
• Pay any tax owed. Even with an extension, any tax due must be paid by the original April deadline to avoid interest and late-payment penalties. 

Why you should file chronologically

• Potential credits and deductions: Filing older returns first allows you to account for any credits, such as capital loss carryovers, that may reduce your tax liability in more recent years.
• Accuracy: Your prior year's adjusted gross income (AGI) may be needed to file electronically for a newer tax year. Filing chronologically ensures this figure is correct.
• Refunds: For any year you are owed a refund, you have a limited time to claim it. Generally, you must file within three years of the original due date. Filing older returns first helps ensure you don't miss out on a refund. 

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[dlumarque]

Thank you all for the detailed answers! Feel free to add more responses but this is exactly the guidance I was looking for.