Pay Taxes by Debit Card and Earn 5X Points
Rewards Credit Cards
Hilary Stockton

My Award Booking Service helps travelers book first class and business class with miles and points. As an independent affiliate of Cadence, I also have access to Virtuoso, Four Seasons Preferred Partner, Peninsula Hotels PenClub, Dorchester Diamond Club, Belmond Bellini Club, Ritz-Carlton STARS, Starwood Luxury Privileges, Rocco Forte and other 5-star hotel partners, so I can book, for no extra cost, your perfect luxury hotel or luxury cruise with VIP amenities not available anywhere else. Become a client and upgrade your stay!

Have a travel question we haven't covered yet? Want to share your secrets for traveling well for less?
It's time to start thinking about taxes, if you haven't paid them already. And as little fun as paying taxes is, getting 5X points for paying them can mitigate some of the sting. Here's one option, which makes use of the Chase Freedom 5X bonus, MyVanilla Debit Card and Vanilla Reload cards.
1. Activate Chase Freedom 5X for January-March 2013

Don't forget to activate your Freedom 5X bonus for January-March 2013 before making your 5X purchases.
Note that up to $1500 in spend per card January-March 2013 receives the 5X bonus, so if your partner and you each have the card, that's up to $3000 in spend that you can get 5X on.
2. Buy a MyVanilla Debit Card and load $500 at CVS

The MyVanilla debit cards are as shown below. I wouldn't recommend them for regular purchases, as there's a per transaction fee and even a monthly inactivity fee. Their best use is for a single large transaction that liquidates the entire card. A number of folks simply get a free cash advance or deposit funds into their bank account, for this reason. For purposes of paying taxes, the ideal is finding Vanilla reloads so you can load this card up with enough to pay your taxes.
Here's what the MyVanilla Debit Card looks like:
Debit Card Taxes - MyVanilla Debit Card
3. Buy Vanilla Reload Cards at $500 each, Load onto MyVanilla Debit Card

Note that CVS generally restricts you to 2 reload or prepaid cards per transaction, so make your purchases of $500 reload cards in increments of 2 cards each time.
4. Pay Taxes
Select which payment processor you want to use. The IRS Web site has a handy chart of the different processors and the fees they charge. As you can see, it's best if you use a debit card to pay, since it just incurs a flat fee, whereas credit cards take a percentage of the transaction.
Use Debit Card to Pay Taxes - Choose Payment Processor
If you and your partner each have the Freedom and max out your 5X bonus at CVS buying the MyVanilla Debit card and reloads, you'll earn 15,000 points for your $3000 in spend.
Your cost to do this will be:
  • $3.95 for MyVanilla Debit Card
  • $3.95 per Vanilla Reload card
  • $2.99-$3.95 flat fee to pay taxes by debit card
  • 2 x 50 cents, because debit card flat fee and actual tax payment billed as 2 different transactions and MyVanilla charges 50 cents per transaction
Let's say your tax bill is $3000. That would equate to $27.69-$28.65 in fees, so 0.92%-0.96%--not bad.
How will you be paying taxes this year to maximize miles and points, at a reasonable fee?
Related Posts


Make Your Own 100,000 Credit Card Bonus Offer


Need Award Booking Help? Our fee is as low as $75 per ticket if you book your hotel through us.

If you enjoyed this, please follow TravelSort on Twitter or  like us on Facebook to be alerted to new posts. 

Become a Member to find your perfect luxury or boutique hotel at up to 50% off: TravelSort Hotels

  • |
  • Print
    print |
Related Articles
Picture?type=large John M. commented 22 Jan 2013
Wow, that's an awesome idea. I'm just not sure which card to put it on. I don't have any cards with a spend requirement left. I suppose it'll be on my SPG Amex. With Amex getting ready to axe the 20% point refund on travel booked with points, I'm angry with them.
Avatar_60_img_0373 NATE S. commented 05 Feb 2013
IS 'MyVanilla Debit Card' a real debit card with a PIN number? I noticed that a lot of prepaid cards although they have 'debit' printed on the card, can't be used as debit but more like a credit card.
Avatar_60_hilary Hilary Stockton commented 06 Feb 2013
Nate, the MyVanilla Debit Card is a real debit card--you get the PIN after registering it (you have to provide your SSN--you can register a maximum of 3 cards to one SSN). Keep in mind though that you'll be charged $1.95, plus whatever the ATM charges--so you'll only want to do this with a large withdrawal, and preferably at an ATM that charges no or low fees.
Leave a Comment
Rewards Credit Cards
Get Free Email Blog Updates
Popular Articles
  Will 10X at Amazon with the Chase Freedom return for Q4 2016? Per a Reddit poster's Chase banker, it will, although so far this is still a rumor: "I was in a branch talking with my [Chase] banker...and I...
  AMEX Small Business Saturday will return on November 26, 2016 (the Saturday after Thanksgiving) but we don't yet know if there will be AMEX targeted offers for statement credit. Previously, 2010-2012, there was $25 statement credit for $25 in small...
  Amazon Fresh can be a new 5X opportunity for grocery shopping, to increase the Ultimate Rewards points you earn from natural spend. 5X on Amazon spend is a significant part of how we earn Ultimate Rewards points via spend...
  Activate your Chase Freedom 5X for Q4, 2016 for the following categories: Drug Stores (including CVS, Walgreens, Duane Reade, Long's Drugs, Rite Aid) Wholesale Clubs (including Costco, BJ's, Sam's Club, Texas Jasmine) Department Stores (Bergdorf Goodman, Bloomingdale's Nordstrom, Macy's,...
  JetBlue is offering 25% Off TrueBlue Awards booked by August 4 for travel September 7 - November 16, although exceptions apply. Here are the details: 25% off JetBlue TrueBlue award travel September 7 - November 16, 2016 Valid for...
  AMEX is offering 2X points at small businesses through the end of 2016, after you enroll your card. Best of all, the offer applies to SPG AMEX cards, as well as AMEX Membership Rewards cards such as the AMEX...
  You can earn 40 AAdvantage miles per dollar at, using the American AAdvantage eShopping Portal. While there have been better deals in the past, of 60X and 50X, 40X isn't bad if you just need to top off...