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For me, this site is a place to learn, get answers, vent or commiserate, or just take a break during the day. It continues to be an invaluable resource that's been a part of my daily routine for 17 years. Eric has taken care of us from the site's inception, mostly unseen, and his work is ongoing. Soon he will migrate the forum to a new host and is waiting for us to get through the 15th before doing so. I've made a donation today and hope others here will consider that as well.

All you can do is file a zero-information federal extension. Gives him 6 months on the SOL to claim any refund, if he finally gets his docs to you next year. We are not their mommies and can't make them do anything. Nor can we allow ourselves to care more about their own taxes than they do. If he has late penalties and interest it's not your fault and there's nothing you could have done to fix it.

I have a client who essentially refuses to make the Jan 15th payment. Now I just give him 3 coupon payments and skip that one.

So many transactions on brokerage statements are clearly motivated by the commissions or bonuses the financial advisor receives. The transactions are relatively small in comparison to the size of the portfolio, so even large gains on a few trades would not move the needle significantly on the whole portfolio. Plus, a disproportionate number of the trades either lose money or eke out tiny gains at best, especially after transaction costs. I’ve always suspected that numerous transactions in a managed account when the client isn’t an active investor are often simply to confuse the client regarding actual performance. It’s pitched as maintaining a “diversified portfolio”, but in fact the best method of diversification is buying and holding the broadest index available with low transaction costs. Rather than looking for needles in a haystack, just buy the haystack.

File an extension and hope for the best. I have a client who brought in his jump drive with all of his bookkeeping and it is a total scrambled useless mess. We asked for his inventory and we got a number three times more than his purchases for the year. A blind man would know that his COGS would be way off. And, of course, even though he is retired from law enforcement, he is far busier than I am and doesn't have the time to get it together and hates bookkeeping and blah, blah, blah. He hasn't gotten his refund yet from last year. I wonder why, even though we tried to work a miracle. I just finished another one tonight who knows far more about taxes than I do. Of course, he went gambling and won a pretty small jackpot (but he can wipe it out with his losses) Nope! You know the rest of the story. If he picks it up tomorrow, he, (rather SHE) is FIRED.

I have a client who doesn't want to mess with making 4 different estimated payments, so I combine her estimates and she makes one payment on April 15th.

Yes, and the earnings are prorated. See Pub. 970, chapter 7 for the calculation.

Not only is there a perceived risk on your behalf if the payment doesn't get made (maybe you typed it wrong?), there is also the problem for people who don't have a lot of money that a withdrawal will get bounced for insufficient funds and then a fee is charged. Who's going to get blamed if there is a problem?

There is also EFTPS that allows scheduling the current and/or future payments at one time. It does give the ability to cancel or change those not yet paid, but the limitations are that it must be linked to one bank account and does not have the other functions that having an IRS account has.

Yep, I have a 95 year old client whose broker is following her conservative risk tolerance but then purchased an oil and gas PTP. No way this woman would ever understand this investment; she hasn't even been able to recognize the 1099-SSA for the last 2 years and was in tears yesterday over the "lost" 1099 that she had all along after we requested a duplicate. She found it today.

We have to be careful with comments on clients' investments. I tell the client do not tell your advisor that your accountant thinks this is a terrible investment (learned the hard way). But I will speak my piece on Limited Partnerships and Publicly Traded Partnerships that brokers buy for a client without running it past them first and with no regard for the tax preparation consequences. I just told a client with what should be a simple return that last year their broker had invested $3,500 of their money in a PTP that generated a -$400 loss and about $1,000 worth of tax forms. Another PTP they owned had $30 income but about 20 entries on the K-1.

I tell them they can lower the amount if they want, but to write it down on the list I gave them &/or make a copy. I push DirectPay and the state equivalent, because they get instant confirmation. I tell them to save the confirmation AND to send it to me each time they pay an estimate. That way I have amounts and dates. If I haven't gotten 3 confirmations from a client by December, I remind them and adjust their 4Q amount if needed. I also strongly suggest the 4Q be paid by 15 December (instead of 15 January the next year) so when they look for all their 2024 expenses, that 4Q shows up as 2024.

I just had an extension. She never makes the estimated payments. Just one big one with the extension.

^ This, or if client changes bank accounts.

That is how I pay our personal estimates.

Never any bad experience. They get vouchers, envelopes, and a payment schedule.

The purpose of the worksheet is to help you determine the net amount on line 2, it is not part of the tax return. The IRS is not watching for an itemized list. As far as that goes, you can just over ride line 2 of schedule SE.

If I reported a single figure I fear it may increase the possibility of getting increased IRS scrutiny.

Since it is just a "worksheet" you don't need to itemize anything. Just put in the total expense and move on.

I had a recently widowed client several years ago with an investment account and so, so many st transactions that had never happened when spouse was alive. I believed the client was being taken advantage of and suggested that she interview a couple of other investment firms to ask how they would manage her account. She swapped brokers within months. Sometimes you just have speak up to alert folks to the possible ramifications of what is happening. It is then their decision to do nothing or take a more active interest. Horse to water, etc.

I also leave the amounts blank on the vouchers in case they want to change the payment amount.

I give my clients a memo with dates and estimated amounts for the four quarterly payments. I print the vouchers for them and even give them envelopes with the address printed. That's it for me. They're on their own the rest of the year. I remind them to make photo copies of both check and voucher. If they want to do direct payments, they're on their own. But I remind them to get some kind of printed confirmation.

Never had a problem with Drake. In fact, I endorse direct debits for estimated taxes instead of relying on voucher coupons for that purpose. My experience with the coupons has been very bad due to the clients. When reviewing for the succeeding year, the conversations go something like this: Frog: "Did you mail in the payments with the coupons I sent you? What about June 15th? Client: "uh, no. Took the kids to Disney World." Frog: "What about September 15th? Client: "uh, no. Our lawnmower broke down and we had to buy a Cub Cadet." Frog: "What about January 15th? Client: "no way. Had to pay credit cards for all those Christmas presents." Frog: "Sorry to hear all that. Looks like you will have to pay (again) this year." Client: "OMG!! Don't tell me that!!! You've got to do something to help me....."

What am I going to do with this guy?! It's every year and getting worse. It's not like April 15th isn't a new date to anyone. The other day I was in the area of his business and managed to pick up his and wife's W-2s from a manager of his business that happened to have copies of the forms. That's another story. He thinks he may have given all his tax documents to his new loan officer at the bank who was going to help him prepare his personal financial statement that the bank requires to renew his business line of credit. He mistakenly thought he'd given me documents. I've asked and reminded him multiple times that I have not received anything from him for 2023 tax year. Today on the phone I had to repeat 3 times that I needed all documents with withholding on them (two 1099-SSAs and 1099Rs for their numerous IRA distributions and wife's pension). He also has a few investment accounts too. He is 80 and a long-time client. I know he's overworked and also in the early stages of cancer treatment, but seriously, what can I do? What would you do?