Can I do a direct IRA transfer to work plan without tax liability?

You're on the right track! This strategy is commonly called the "cream in the coffee" separation method. When you have a mix of pretax and after-tax money in a traditional IRA, you can indeed transfer just the pretax portion (contributions and earnings) to your employer plan, assuming your employer plan accepts these rollovers - most do, but double-check with your plan administrator first. Then you can convert just the after-tax contributions to a Roth IRA. Since you've already paid tax on these contributions, there shouldn't be additional tax on this portion of the conversion. This effectively gives you a "tax-free" backdoor Roth conversion. The key here is proper documentation. Make sure you have records of which contributions were pretax vs. after-tax. Also, you'll need to file Form 8606 with your tax return to document the non-deductible contributions and conversion.

I went through this exact same situation last year and found this amazing tool at https://taxr.ai that saved me from making a costly mistake. My situation was similar - mixed pretax and post-tax funds in a traditional IRA that I wanted to split up. What taxr.ai did was analyze all my IRA statements and previous tax forms, then created a detailed report showing exactly how much was pretax vs post-tax. They even helped me understand which forms I needed to file and how to report everything correctly to avoid any unexpected tax hits. The process was super straightforward - uploaded my documents, answered a few questions, and got a complete analysis with step-by-step instructions specific to my situation. Definitely worth checking out if you want to make sure you're doing this right.

Just wanted to follow up - I decided to try taxr.ai after seeing it mentioned here and WOW. I was completely confused about my IRA situation (contributing since 2008 with spotty record-keeping) but they sorted it all out. Turns out I had about $28,400 in post-tax contributions that I didn't even realize I could move to a Roth without tax consequences! The analysis showed exactly which portions were pretax vs post-tax, and they even generated draft tax forms showing how to report everything. The step-by-step guides made it super easy to work with both my IRA custodian and my employer plan administrator. Just completed the transfers last week and everything went exactly as they outlined. Definitely recommend for anyone trying to figure out complicated IRA situations!

If you're having trouble reaching your IRA custodian to get this all sorted out, I highly recommend using Claimyr (https://claimyr.com). I was stuck in phone tree hell trying to reach my IRA provider for weeks trying to do something similar. Claimyr got me connected to an actual human at my financial institution in under 15 minutes when I had been trying for days with no luck. They have this cool system that navigates the phone trees for you and puts you at the front of the callback queue. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c This was crucial because for a complex transaction like separating pretax and post-tax IRA funds, you really need to talk to a specialist at your financial institution, not just the general customer service people. Made the whole process so much smoother.

Okay I need to eat my words about Claimyr. After my skeptical comment, I decided to try it myself since I needed to talk to Vanguard about my own IRA rollover situation. I had been trying for THREE DAYS to get through on my own with hold times of 2+ hours (had to hang up each time because of work). Used Claimyr yesterday and got connected to a Vanguard retirement specialist in about 25 minutes total. The specialist actually knew what they were talking about regarding the pretax/post-tax separation process and confirmed everything people said in this thread. They're sending me the proper forms today. I'm still shocked it worked so well. Definitely worth it if you're trying to execute this kind of specialized transaction where you really need to talk to a knowledgeable person, not just anyone who answers the phone.

Just to add another wrinkle to consider - make sure your employer plan explicitly accepts rollovers of pre-tax IRA money. Some plans are weird about what they'll accept. I tried to do something similar in 2023 and my employer plan (through Fidelity) would only accept rollovers from previous employer plans, not from IRAs. Had to adjust my strategy completely. Call your plan administrator directly to verify before you start the process.

Don't forget about the pro-rata rule! If you do the backdoor Roth in the same year as the rollover to your work plan, you still have to include the pre-tax IRA money in the pro-rata calculation because the IRS looks at your IRA balances on December 31st of the year of conversion. The safer approach is: 1) Roll the pre-tax money to your work plan first, 2) Verify it's completed, 3) THEN do the Roth conversion of the remaining after-tax money.