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This doesn’t answer your main question but did you enter each W2 separately?   Just checking.  They probably needed to go on 1 W2.   If the EIN number is the same and you work in more than 1 state or city, sometimes they will give you another W2 with the extra state information on it and the top part the same or not filled in.  If this is the case, list one W-2 but include both state or local  taxes on it.  It will let you type in more than one line for boxes 15-20.  Don't add the boxes together.  

Contribution to retirement will depend on whether you filed an extension or not and the type of the account. If there was no extension filed, then you cannot contribute to any retirement plan but if there was an extension filed, you can still contribute to  Self Employed retirements plans. The exact date and which contributions are allowed depend on your business structure and when the plan was established.    Some of the most common retirement plans for self-employed are Solo 401k, SEP IRA and SIMPLE IRA.  Deadline to open Solo 401k is Dec 31st in the year you want to contribute so for 2024 tax year, that deadline has passed.  The deadline to establish and contribute to a SEP IRA is your business's tax filing deadline, including any extensions. You can set up a SIMPLE IRA plan effective on any date between January 1 and October 1, provided you (or any predecessor employer) didn't previously maintain a SIMPLE IRA plan. This plan also has to be opened during the tax year in order to contribute.     Three are also some other retirements plans. See below for more info. about different types of plan.  https://www.irs.gov/retirement-plans/retirement-plans-for-self-employed-people   Thanks for participating in TurboTax's Ask the Expert event today. I hope this information was helpful! **Please cheer or say thanks by clicking the thumb icon in a post **Mark the post that answers your question by clicking on "Mark as Best Answer" Regards, TurboTax Expert

You may not have received a Schedule K-1 if you were just distributed assets from the estate.  The estate should have reported the income and paid the taxes in which case you would not receive a K-1.   You should contact the entity for which you should be receiving this Schedule K-1.  It may be that they extended their tax return.     If this is the case then they have until September 15th to file their return.  You will also need to file an extension for your Individual Tax Return.  When you do this, you will then have until October 15th.   If you're thinking of filing before you get a certain form: do not do it. You should not file a return when you know that it is missing information.   The IRS specifically prohibits tax preparers from filing tax returns unless all W-2, W-2G, and 1099-R forms are received. Furthermore, filing without all the proper forms could trigger an audit. If you should have received a form already and haven't, then you should continue to contact the company that was supposed to issue it. I hope that you do receive your K-1 before the October 15 deadline.   Helpful links: File An Estate Tax Income Tax Return   

So, "investment" -- maybe.  Investment losses are deductible against investment gains.  Theft losses are not deductible.  Sometimes it is difficult to determine whether a loss is from a theft or an investment loss.  The IRS recently issued some new rules.  If you have questions, it would be best to discuss with your own tax professional with whom you share all the details.   https://www.slatterycpa.com/irs-clarifies-theft-fraud-loss-deductions-scams/   https://www.taxpayeradvocate.irs.gov/news/nta-blog/irs-chief-counsel-advice-on-theft-loss-deductions-for-scam-victims/2025/04/   https://www.thetaxadviser.com/issues/2025/feb/taxpayer-denied-theft-loss-deduction-for-investment-loss/   https://www.forbes.com/sites/matthewroberts/2025/03/19/irs-surprises-taxpayers-with-new-ruling-on-theft-losses-after-tcja/

The TurboTax user license allows one user to install copies of TurboTax on up to five computers that the user owns. When you initially install the software, the product code is tied to your TurboTax account. The same account must be used for each install. If you have not exceeded the 5 installs, and have verified the product key and account being used are correct, your next best step is to contact TurboTax Support for further troubleshooting: How do I contact TurboTax? 

This seems strange. It sounds like I could convert a taxable transaction into a nontaxable one simply by not selling shares from my portfolio and instead transferring them into my Roth IRA and selling them from there. Am I missing something?

Sorry---by saying that you were "Head of Household" on your W-4, you had too little tax withheld from your paychecks.  Filing as head of household requires you to have a qualified dependent that you support.   By using HOH as a filing status on your W-4, you told your employer to withhold less than than the employer would have withheld if you had said you were single.  There is no "fix" that will lower your tax due now.      Correct your W-4 going forward to prevent this from happening again.   W-4 https://turbotax.intuit.com/tax-tools/calculators/w4/  https://www.irs.gov/individuals/tax-withholding-estimator         Am I Head of Household?   https://ttlc.intuit.com/turbotax-support/en-us/help-article/tax-filing-status/qualify-head-household-2021/L0NxUtVc2_US_en_US?uid=m5x19jkx What is a "qualifying person" for Head of Household?   If you qualify as Head of Household, when you enter your marital status (single or married filing separately) into MyInfo, and then enter your qualifying dependent, TurboTax will offer HOH as your filing status.     To apply for a payment plan with the IRS   Apply Online for a Payment Plan https://www.irs.gov/pub/irs-pdf/fw4.pdf  

FYI- And even if the IRS allows efiling for 2022 & 2023,  Turbo Tax only lets you efile the current year 2024.  To efile prior years you would have to find someone else.  Probably a local accountant.