What is the Simple IRA Contribution Deadline for 2023 paychecks received in 2024?

Thanks for the quick response! So even if the pay period was entirely in 2023 (December 16-31), if I don't physically receive the money until January 2024, then any Simple IRA contributions from that check would count toward 2024? That's disappointing - I was really hoping to max out 2023. Would it make any difference if my employer were to process the payroll earlier? Like if they could somehow get the 12/31 paycheck to me on 12/31 instead of mid-January?

Yes, it's all about when you actually receive the payment, not when you earned it. The IRS is pretty clear that Simple IRA contributions through payroll deduction happen when the money is paid to you. If your employer could process the payroll earlier and actually pay you in December, then yes, it would count for 2023. However, many companies have fixed payroll schedules that are difficult to change, especially around year-end when they're dealing with W-2 preparation and other tax matters. It doesn't hurt to ask, but don't be surprised if they say it's not possible.

Does taxr.ai actually connect you with real tax professionals, or is it just some AI thing that spits out generic advice? I've been burned before by "tax help" websites that just regurgitate IRS publications without actually addressing my specific situation.

Sounds interesting but I'm wondering how personalized the advice really is. Like, would it know about specific rules for someone who's partially self-employed and also works for a company with a Simple IRA? My situation is complicated and I'm trying to maximize contributions across different retirement accounts.

It connects you with actual tax professionals who review your specific situation after the AI does an initial analysis. I was skeptical too, but they helped me understand exactly how my December pay affected both my Simple IRA limits and what other options I had. For self-employed situations, they're actually really good at that. My spouse has a side business along with a regular job, and they provided detailed guidance on how to handle contributions across different retirement vehicles to maximize tax advantages while staying within limits. They walked us through exactly what forms we'd need and the timing requirements for each account.

How does this actually work? Do they have some special access to the IRS phone lines or something? Seems kinda sketchy that they could get through when everyone else is stuck on hold for hours.

Yeah right. There's no way this works. I've called the IRS like 30 times this year and NEVER got through to anyone. If this service actually worked, everyone would be using it. I'm betting it's either a scam or they just take your money and you still end up waiting forever.

They don't have special access - they use technology to continuously call and navigate the IRS phone tree until they get a spot in line, then they connect you. It's all above board - you're still talking directly to the IRS, they just handle the waiting part. It's not a scam at all. The way it works is pretty straightforward - they have systems that keep calling and navigating the phone menus until they finally get in queue, then they call you to connect. You're still talking directly to an official IRS agent, just without the hours of waiting. I was skeptical too until I tried it.

I didn't even think about that! Do you know if I can have both a Simple IRA through my employer AND contribute to a separate Traditional IRA? Is there any impact to the deductibility of Traditional IRA contributions if you also have a workplace retirement plan?

You can definitely have both a Simple IRA and a Traditional or Roth IRA. However, being covered by a workplace retirement plan (like your Simple IRA) does affect the deductibility of Traditional IRA contributions based on your income. For 2023, if you're covered by a workplace plan, the deduction for Traditional IRA contributions starts to phase out at $73,000 for single filers and $116,000 for married filing jointly. If your income is above those thresholds, you might want to consider a Roth IRA instead (which has its own income limits) or a non-deductible Traditional IRA contribution that could potentially be converted to a Roth later (the "backdoor Roth" strategy).

My company does this too! We specifically asked about it a few years ago because several employees wanted to max out their retirement contributions, and now they just automatically process the last paycheck of the year earlier. It might be worth asking - the worst they can say is no.

That's a great idea! I just called my payroll department and asked about this. They said they normally don't change their schedule, but since there are several employees in my situation, they're going to bring it up with management to possibly process the final 2023 payroll on December 29th instead of waiting until January. Fingers crossed this works out - thanks for the suggestion!