Tax Day 2019: Money-Saving Tips for Everybody (Even If You've Already Filed)

Our hosts Ryan Ermey and Sandy Block walk you through all the last-minute advice you need to file your taxes -- from common errors to avoid to filing an extension to free filing software. The pair also discuss Tax Day consumer deals and freebies you don't want to miss.

Ryan Ermey: Well, it's April 15th. Have you filed your taxes yet? Don't worry, we've got you covered. On today's Tax Day extravaganza, Sandy and I discuss filing for an extension, free last-minute software options and common procrastinator mistakes, before wrapping up with a collection of Tax Day deals and freebies. That's all ahead on this episode of Your Money's Worth. Stick around.

Ryan Ermey: Welcome to Your Money's Worth. I'm Kiplinger staff writer Ryan Ermey, joined by senior editor Sandy Block -- and Sandy, we finally made it. It is Tax Day, at last. We're going to try to get this show up as early as we can, so you can listen and then go file your taxes.

Sandy Block: Do your taxes. That's right.

Ryan Ermey: That's exactly right, but I guess we wanted to kick things off here with -- just in case you're not going to make it under the deadline today -- what's going on with filing an extension.

Sandy Block: That's right. If you absolutely cannot get your taxes done by midnight tonight and you don't owe, there's no need to panic. You can file for an extension and you'll get an automatic extension until October 15th. It's not like when you hand in your homework late and you have to give a reason.

Ryan Ermey: Right.

Sandy Block: The IRS will do-

Ryan Ermey: Right. Sure.

Sandy Block: ... you know, the dog didn't ... you know, the IRS will give you an extension. Now, the most important thing to remind people is that an extension does not give you more time to pay. If you owe, you should pay as much as you can by midnight tonight or interest and penalties will start to accrue, but if you're like most people and you're going to get a refund and you really don't have it together, maybe there's some form you haven't found or you just haven't gotten around to doing it, you're much better off filing for an extension and getting it right than rushing to file at the last minute and potentially overlooking some valuable deduction or credit or leaving out some taxable income that could get you a letter from the IRS. Filing an extension can be a smart thing and as I said, you get six months. You could do it next week, but you can wait until October.

Ryan Ermey: Logistically what does that look like? Does it make sense to file electronically, to mail something in?

Sandy Block: You can do either way. I would say electronically is faster and more efficient and there are lots of ways you can do that. Tax preparation software will file the form, you can go to and find the form on the free-file site, so there's lots of ways you can do it electronically. The form specifically is 4868. If you must use a paper version, you have to have it postmarked by the original deadline, which is today, and you have to use the US Postal Service to mail the form. Don't get UPS or something like that. That won't work. Basically, as I said, it's pretty easy, it's seamless, and as long as you don't owe, why not give yourself a little more time and go to bed early.

Ryan Ermey: We did want to make a mention of some content that we have on as we speak. There are nine states, from what I understand, where the filing deadline isn't actually April 15th for the state taxes.

Sandy Block: That's right. Now, we recommend that you file your federal and state tax returns at the same time. Most tax software programs will do both and a concern is if you do wait to file your state tax returns, you might forget, but if for some reason you just can't get it together for your state, depending on where you live, you might have more time. In some cases, it's just a few days. If you live in Maine or Massachusetts, your taxes are due April 17th, Hawaii and Oklahoma, April 22nd. If you live in Virginia, and I do, you have until May 1st.

Ryan Ermey: Hey.

Sandy Block: Hey, yeah, and last but not least, if you live in Louisiana and you've just spent too much time partying in New Orleans, you have until May 15th to file your Louisiana taxes. Again, we don't really recommend this. It's better to just get it all out of the way today, but it is helpful to know that in some cases you have a little more time to file your state tax return.

Ryan Ermey: Is there a reason behind any of these things? Like rhyme or reason?

Sandy Block: No, I don't think so. I think in Maine and Massachusetts it has to do with Patriot's Day.

Ryan Ermey: I think it might as well, yeah.

Sandy Block: Right?

Ryan Ermey: Boston Marathon's usually right around this time. It's always on Patriot's Day.

Sandy Block: Yeah, you've got to run the marathon. You don't have time to do your taxes or go out and cheer for people who are running it, whatever.

Ryan Ermey: Sure, absolutely.

Sandy Block: I don't know why the other states give more time. I think it leads to potential for more confusion and more forgetting, but it is out there and for some reason you need to take advantage of it, we'll post the whole list on our show notes.

Ryan Ermey: Yeah. Like we said, if you need more time to figure it out, especially if you don't owe money, go ahead and take the extension. It's easier if you ... like we said, if you're hung over from drinking hand grenades in New Orleans, take your time getting that state tax return in, but otherwise, we're gearing the show, the bulk of the show, for people who are paying on time. Hopefully, all of you have paid months ago and don't even have to worry about it. Well, hopefully not because hopefully you're listening, but the bulk of our segment is going to be for people who are paying today, so we'll have that right after the break.

Ryan Ermey: Coming up, don't fall prey to last-minute tax mistakes that will cost you money. Don't go anywhere.

Ryan Ermey: All right. We are back, so for the people who are paying today, obviously, they've waited until the last second to do it, but I think that's what a lot of Americans do. We wanted to go over a couple things. The first being common last minute errors and how to avoid them.

Sandy Block: That's right, Ryan, and the takeaway here is just as your school teacher said, when you do your taxes, check your work because mistakes can really cost you a lot of problems. One, and I'll just kind of go down the list of common tax payer errors that could derail your tax return, get it bounced back, or actually cost you some money, the first one I'll mention is wrong Social Security number. Now, you might think, I know my Social Security number, I'm not going to get that wrong, but what happens a lot of times is people's Social Security numbers do not match their name. If you got married and changed your name, but you didn't file with the Social Security Administration, your tax return could bounce back because that's one of the things that the IRS uses to protect against fraud.

Ryan Ermey: What do you mean by bounce back?

Sandy Block: It will be ... well, assuming you're filing electronically here.

Ryan Ermey: Right.

Sandy Block: You file electronically and it gets rejected-

Ryan Ermey: Oh, I see.

Sandy Block: ... because it doesn't match up or you get something later saying your tax return was rejected because your name doesn't match your Social Security number.

Ryan Ermey: Then, in that case, does that mean that you're going to accrue penalties for late payment?

Sandy Block: Right, if you owed. If you owed and-

Ryan Ermey: Oh, I see.

Sandy Block: ... if you have a refund, you're just not going to get your money, which is bad, too. If you have kids, you need to include Social Security numbers for them and any other dependents that you have otherwise you might have some valuable child tax credits disallowed or reduced, so make sure that those numbers are right, too.

Sandy Block: The second one I'm going to mention is really important and I have to confess that I did make this mistake. That's if you file electronically and have your refund deposited in your bank account or you owe and you have your bank account debited, make darn sure that you use the right account number, and that's an easy mistake to make because if you look at a check, you've got the whole account number and the routing number that you have to enter in your program. I did this wrong once and fortunately, in my case, actually I owed, so I ended up, it was like a bounced check. I got a note from the IRS saying you didn't pay.

Ryan Ermey: Right.

Sandy Block: Think about if you have a refund, and you put in the wrong account number, and it goes out, you think that they're going to call you up or the ... the IRS isn't going to go looking for your refund for you. You're going to have to go find it, so double, triple, quadruple check your bank account number if you have a question about what is the account number and what is the routing number. You can go to your bank website or just Google and it will show you.

Ryan Ermey: Yeah, I copy and paste them in.

Sandy Block: That's not a bad idea because it's really easy to get ... I mean, there's a lot of numbers there and like I said, the mistake here could be really, really dramatic. You have to sign and date your return and if you're filing jointly, your spouse has to sign, too. If you're doing this electronically, there's a method to do that.

Ryan Ermey: Sure.

Sandy Block: The last thing I'll mention is just to make sure that you report all of your income. A lot of people might be lured into complacency when they see these numbers about how few people get audited by the IRS-

Ryan Ermey: Right.

Sandy Block: ... but what they may not realize is an enormous amount of the work that the IRS does is automatic. It gets forms from your banks, maybe even someplace where you won gambling money. It gets 1098s and 1099s from all these institutions and then, when you file your tax returns, it looks to see if you reported this income to match it up. If it doesn't, you will hear from them, so make sure that you report all of your income. If you think that you might have overlooked something, maybe there's a 1098 or 1099 out there from your brokerage account that you can't find or you're not sure about, that's a good reason to file for an extension because that could cause problems for you.

Ryan Ermey: Yeah, you hear that, Dad? My dad's been cheating on his taxes for years. No, this actually isn't true. Not true at all, but the last couple times I've talked to my parents, all they ... they give me so much trouble for saying, "You talk about us on the podcast. Why do you always bring us up?" I'm like, "It's completely harmless." Like, they're going to be embarrassed in front of their friends, like oh, I said that my dad cleans out his garage. Listen, this is what it could be Mom and Dad. I could be telling the world that you cheat on your taxes, so back off. I'll mention you whenever I want.

Sandy Block: Don't cheat on your taxes.

Ryan Ermey: Well, no, and they don't.

Sandy Block: They don't cheat-

Ryan Ermey: They're outstanding people.

Sandy Block: Again, like I said, this is one thing that you do need to make sure that anything and even something maybe ... a lot of times people have bank account and their interest is so small that they think, they forget about it.

Ryan Ermey: Negligible.

Sandy Block: That interest has been reported to the IRS, so the IRS might come after you for those $35 that you have in your bank account in interest over the last year that you didn't report. Make sure you report everything to them that has been reported from someone else.

Ryan Ermey: Okay. Then, the other thing we wanted to talk about was that maybe it's too late for you to get professional help doing your taxes, so where should people be looking for last-minute free, online resources.

Sandy Block: Yeah, I would be a little ... I think any tax preparer at this late date is either going to charge you a lot of money or not do a very good job, so I think it's kind of, that train has left the stations in terms of getting professional help. You'd probably want to file for an extension, but say you do want to file your taxes, you don't want to pay for it there are still lots of free options. We mentioned them on our website, so we'll put them in the show notes, but a few that I'd like to point out is H&R Block Free, that's H&R Block's online program. If you have W-2 income, claim the standard deduction, pretty straightforward return, you can use that. Credit Karma Tax, which we've mentioned before is available. There are a few forms it doesn't support, but not many, so even if you have a complex tax return, you can use them. The last one I want to mention that is so often overlooked, IRS Free File.

Ryan Ermey: Right.

Sandy Block: If you have, which Ryan, as you've said, you've used. If your income was $66,000 or less, you can go to, look up Free File and there will be 12 options available to you. You may not be eligible for all of them, but you should be able to find one or two that you can use. Some charge you for a state tax return, others don't. You don't have to have a simple return. They'll basically support most tax returns and there's all kinds of political and interesting reasons for this, but this is really not used by very many people and one of the sort of unfortunate circumstances I think is because there are other free programs out there. They tend to show up higher on Google search than Free File.

Ryan Ermey: Oh, I see.

Sandy Block: Some of these other free programs, it can be very ... find yourself being forced to upgrade very easily and Free File really is free, at least for your federal tax return, so go there.

Ryan Ermey: Yeah, and it's not like off-brand stuff either. I use Free File and I use H&R Block through Free File.

Sandy Block: Yeah. I mean, and Turbo Tax, as I said, they have different criteria, but there's a tool there that you can use to find a program that suits you. You may have to pay for a state tax return, you may not, but it is available. It will be there for you all night long, right up through the deadline. I actually think at this point it probably is a better bet than trying to find someone to do your taxes for you.

Ryan Ermey: All right. There you have it. Get on the stick, folks. After the break, Sandy and I pit the best Tax Day promotions against one another to find out who offers the very best deal. Come on back.

Ryan Ermey: Okay. Before we go, if you've stuck around this long, you deserve to be treated to something nice and after years of doing the financial calendar in the front of the magazine-

Sandy Block: Doing it really well.

Ryan Ermey: ... thank you very much ... I have learned all sorts of different Tax Day freebies and discounts. I've narrowed them down to my eight favorites for a small bracket-style tournament.

Sandy Block: April madness.

Ryan Ermey: Yeah, exactly. Well, and I favored ones that were legitimately free. Like, I don't consider like, oh, if you buy this, you also get ... that's not really free.

Sandy Block: No.

Ryan Ermey: You still have to purchase stuff. I mean, just missing the cut on that front, if you buy an adult meal, you can get a free kid's meal on Tax Day at Hooters.

Sandy Block: Who's going to take their-

Ryan Ermey: I've always wondered.

Sandy Block: I want to see who takes their kid to Hooters.

Ryan Ermey: Son, spent all night crunching the numbers-

Sandy Block: ... and it's time for you to learn what it's like to be as an adult.

Ryan Ermey: It's time to go to take your children to Hooters. That didn't make the cut.

Sandy Block: Good.

Ryan Ermey: We had just an eight-deal bracket-

Sandy Block: Okay.

Ryan Ermey: ... that we're going to go through here.

Sandy Block: Get this party started.

Ryan Ermey: We're going to start in the food region.

Sandy Block: Okay, because you're hungry after doing those taxes.

Ryan Ermey: We have the food and the non-food region.

Sandy Block: Okay.

Ryan Ermey: Four options in each. In the food region, our first match-up is what I call the treats match-up, so on one side we have Kona Ice, which is-

Sandy Block: Like, shaved ice?

Ryan Ermey: Yes. Delicious ... tropical shave ice. It's available ... it's trucks that sell them. On Tax Day, you'll get one free shaved ice, your flavor of choice, available in 48 states, so that's one option.

Sandy Block: Okay. Not Hawaii where shaved ice comes from. That's weird.

Ryan Ermey: Well, I don't know if Hawaii's one of the 48. I just know that there are 48.

Sandy Block: Okay, I'm guessing it's not.

Ryan Ermey: I mean, it might be, you know, Alaska and Hawaii might be in and like Jersey and Nebraska might be out. Who knows?

Sandy Block: All right.

Ryan Ermey: The other is, you know, I combined a couple of these for what I'm calling mall treats. One is Great American Cookie is giving one free chocolate chip cookie to everyone on Tax Day. These seem to be abundant in shopping malls sort of like Nebraska and east.

Sandy Block: Yeah, yeah, yeah.

Ryan Ermey: Then, on the West Coast and the Southwest, we have a chain that I had never heard of called Hot Dog On a Stick-

Sandy Block: I've never heard of it.

Ryan Ermey: ... which is giving away one free turkey or veggie, I believe, corn dog. What are we thinking?

Sandy Block: Oh, I've got to go with the cookie, Ryan.

Ryan Ermey: Wait, a cookie/dog or shaved ice?

Sandy Block: Oh, oh, right, right. Okay. Oh, cookie.

Ryan Ermey: All right we're going to go with the cookie/hot dog depending on where you are in the country.

Sandy Block: Not the hot-

Ryan Ermey: Yeah. I mean, you got a raw deal over there. I'm sorry. Alright. Second food match-up in the savory category.

Sandy Block: Oh, okay.

Ryan Ermey: Now, between 7:00 and 10:00 AM, so you better be listening to this podcast early and-

Sandy Block: Or West Coast.

Ryan Ermey: ... step on it. Yeah, that's right.

Sandy Block: West Coast.

Ryan Ermey: West Coast. You can get a free sausage biscuit at Hardee's. You just have to say the phrase, "Made from scratch," when you go in.

Sandy Block: Not, "I did my taxes?"

Ryan Ermey: Nope, made from scratch.

Sandy Block: Okay.

Ryan Ermey: That's one option. The other ... now, see, I was going to do one here, but a lot of these restaurants are kind of sketchy about their deals, and one kind of fell through here, but one that is lasting from April 15th to the 21st is at Walmart. If you clip a coupon from and buy a dozen eggs at Walmart, they're free with the coupon. You just have to submit your receipt for reimbursement, so free sausage biscuit sandwich or free dozen eggs.

Sandy Block: I'm going with the sausage biscuit sandwich-

Ryan Ermey: Yeah, me too.

Sandy Block: ... because if I buy the eggs, I've got to make my own sausage biscuit sandwich.

Ryan Ermey: You're quite right.

Sandy Block: Yeah.

Ryan Ermey: Alright, so those two moving on. Now, into the non-food region. We have what I'm calling the practical matchup. One is something that we just talked about and this might be possible. It started back in February, but it does go through April 15. The AARP Foundation provides free, in-person tax assistance and preparation through its Tax Aide Program.

Sandy Block: Right.

Ryan Ermey: You can find someone through the AARP website. If you make it there today, it's very possible that you could get some free, in-person tax assistance, which is-

Sandy Block: I bet you'd have to wait in line, though.

Ryan Ermey: Probably.

Sandy Block: Yeah, it's April 15th.

Ryan Ermey: Well, although, maybe not. Maybe it's like, maybe you beat the rush, who knows? The other option is a classic Office Depot and Office Max, you get up to five pounds of free paper shredding through April 27th.

Sandy Block: Oh, I've got to go with the paper shredding.

Ryan Ermey: Yeah, me too. It's a good deal.

Sandy Block: Yeah, that's a lot.

Ryan Ermey: Five pounds, that seems to me to be a lot of paper.

Sandy Block: What do they ...? I want to go down there and see what they do with it.

Ryan Ermey: It's like a real sort of like Watergate kind of scenario. Destroy a lot of documents. Okay, then the last one I'm calling unwind. A lot of these deals are supposed, you know, they're kind of advertised as-

Sandy Block: You're tense. Yeah.

Ryan Ermey: Yeah, yeah, yeah, yeah, you're stressed, how do you unwind? One is Planet Fitness offering use of its hydromassage chairs for members and non-members for free through April 20th.

Sandy Block: Okay.

Ryan Ermey: Now, I don't know about you, but I used to go sit in the ones in Brookstone or whatever in the mall. I feel like a massage chair is never really as satisfying.

Sandy Block: Did you ever try the ones in the airport? They have those in the airport sometimes.

Ryan Ermey: Yes, and you know what? That's actually not bad. I actually, once in the Amsterdam airport I sat in one, it was like a chamber that you lie down in with water up to your ears and you're on your back. Then, there was some sort of felt like water. You weren't getting wet, but it was like you were compressed in like a chamber.

Sandy Block: Oh, man.

Ryan Ermey: When you have six hours to kill in the Amsterdam airport, you go to the casino, you get the massage.

Sandy Block: Alright.

Ryan Ermey: Although, don't go to the casino.

Sandy Block: No.

Ryan Ermey: Dealers win pushes on Blackjack in the casino.

Sandy Block: Sideways tip there, pal.

Ryan Ermey: I mean, really rough. Yeah, tax tips and international gambling tips. All right, so our second option in the unwind section is Applebee's for, you know, your local Applebee's, for the month of April is rolling out the new Strawberry Dollarita, which is a 10-ounce strawberry flavored margarita in a mug that, you guessed it, cost a dollar. Times vary on when it may be offered at your local Applebee's, but regardless, each of them is served in lieu of a straw is a strawberry Twizzler that you drink out of just in case it wasn't enough sugar in the drink.

Sandy Block: Clever.

Ryan Ermey: Alright, so we going for massage or Dollaritas?

Sandy Block: Oh, that's a tough one. The Dollarita just makes my head ... it sounds like something that gives you one of those headaches. You know?

Ryan Ermey: Yeah.

Sandy Block: I think I'd go with the massage.

Ryan Ermey: Okay.

Sandy Block: Seems less dangerous.

Ryan Ermey: Going back to the top of our bracket, I believe we have the biscuit versus the cookie/hot dog.

Sandy Block: Yeah, I'm going for the cookie.

Ryan Ermey: Yeah, alright. Mall treats.

Sandy Block: Yeah.

Ryan Ermey: Mall treats advances to the final.

Sandy Block: Cookie, cookie.

Ryan Ermey: Then, we have massage or shredding.

Sandy Block: Oh, shredding.

Ryan Ermey: Shredding?

Sandy Block: Shredding, yeah, shredding.

Ryan Ermey: Alright, well, then finally, shredding or cookie?

Sandy Block: Shredding.

Ryan Ermey: Alright.

Sandy Block: Five pounds.

Ryan Ermey: I mean, it really is a lot.

Sandy Block: That's a lot.

Ryan Ermey: It is a lot.

Sandy Block: Of course, you've got to get it there.

Ryan Ermey: Yeah, and I also don't know, like I have no concept of what that costs normally.

Sandy Block: Well, all right. Even if you have a shredder, and I do, five pounds is going to stop your ... I mean, unless you've got a really good shredder, mine tends to freeze up after half a dozen sheets.

Ryan Ermey: Oh, I see.

Sandy Block: Five pounds would blow that thing out.

Ryan Ermey: This is industrial grade shredding.

Sandy Block: I want an ... Yeah, I think the lure here is having an industrial size shredder to get rid of ... We'll talk about this at some point, but you don't have to keep a lot of these tax documents forever-

Ryan Ermey: Right.

Sandy Block: ... and sometimes it's a good idea to get rid of some of them just to make room and get more organized. This sounds like a good idea to get rid of stuff you don't need anymore.

Ryan Ermey: All right, so there you have it, folks. I mean, let us know if you agree or disagree with our bracket. We did the best we can out here, but take advantage of any and all deals you can. You've worked hard all year, you've finally paid your taxes, you made it, sit back and relax and enjoy one or two or 12 Dollaritas, responsibly of course.

Ryan Ermey: That will do it for this episode of Your Money's Worth. For show notes and more great Kiplinger content on the topics we discussed on today's show, visit You can stay connected with us on Twitter, Facebook or by emailing us at If you like the show, please remember to rate, review, and subscribe to Your Money's Worth wherever you get your podcasts. Thanks for listening.

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