Credit Cards, Travel

Our First Travel Hack: Two Weeks in Greece Using Chase Ultimate Rewards Points

You guys have graciously followed my credit card journey for a year and a half now. You supported me when I departed from the anti-credit card stance that I had long held, learned with me as I adjusted to new ways of maintaining our budget now that almost every purchase was put on credit cards, watched our number of points grow each month, waited impatiently with me for my husband to choose our next travel destination, and you rejoiced with me when at long last, he announced that we were going to Greece.

And now, after booking three flights and five hotels for our two week stay, I’m excited to share with you our experience in redeeming those points for the very first time!

But first, let’s talk about the concept of travel hacking for anyone who isn’t very familiar with this term.

Travel Hacking

What is travel hacking?

While the strategies certainly can get complex depending on how much time and effort you’re willing to dedicate to travel hacking, the intent is simple: opening specific credit cards for the purpose of earning large signup bonuses, then redeeming the bonus points (as well as points earned along the way) for free/cheap travel. This encompasses flights, hotels, vehicle rentals and even activities.

You may be wondering, “But what’s the hack?” As sneaky, immoral or even illegal as it sounds, all that is being hacked is the game played by credit card companies. After all, they expect that you will end up paying them much more over time than they pay you initially through the form of signup bonuses – which brings us to our next point.

Who can benefit from travel hacking?

Keep in mind that I’m a debt-free, Dave Ramsey Baby Step Sevener, so I am extremely conservative when it comes to who I wouldn’t be concerned about experimenting with travel hacking for themselves. I word it this way because I do not recommend travel hacking for anyone. Only you can know if you have the extreme discipline, organization and habits required to win at this game.

Someone who has the potential to excel at travel hacking will need the following habits and qualities at the very least:

  • Responsible use of credit cards, or even better, someone who has never felt compelled to use credit cards. No carrying a balance, no paying even a penny of interest, and no temptation to overspend. If credit card debt or overspending in any form has ever been a struggle for you, I would not attempt travel hacking.
  • An excellent credit score.
  • Systems, organization, automation, planning, preventative financial maintenance and more systems, systems, systems.
    • Credit cards with high bonuses do not come with unlimited time to earn these bonuses. You have a certain amount of time to spend a certain amount of dollars, and if you live frugally like my husband and me, a certain amount of planning around large purchases will be necessary to meet these spending limits. You will need to keep up with how much is spent during this time limit to make sure you meet it. Otherwise, opening the card for the purposes we’re discussing is pointless.
    • To expand on the subject of intentional spending, your finances will need to be organized and maintained regularly in the form of a budget to ensure you are not overspending.
    • Most travel rewards cards come with annual fees, and you will have to plan for this upfront “expense.”
    • You will need to figure out a way to make sure you pay in full and on time every single month, whether that’s by simply setting up the card to be paid on the due date by automatically withdrawing the balance from your checking account once per month, using a free third-party service or by manually paying off the card in more frequent intervals such as biweekly, weekly or even daily.

Why did we decide to begin travel hacking?

I had come across the idea from time to time over the last few years, but it was something that sounded not only too complicated for me, it sounded risky. A decade of believing credit cards were evil led to my assumption that anyone who used credit cards for almost-free travel were being screwed in some way, in the forms of overspending, paying interest, or just overall creating a huge mess that they would eventually have to clean up.

However, after creating this blog and my subsequent Instagram account, I began to learn points of view from personal finance bloggers and podcasters that weren’t Dave Ramsey or his team, and I started to see that many people actually were successfully travel hacking – and it wasn’t as complicated as I had always brushed it off to be.

An early episode of ChooseFI sealed the deal for me one weekday morning while I was sitting in my cubicle at work. In the episode, aptly titled How to Travel the World for Free (The Easy Way), the hosts explain the concept, share their own unique experiences and reasons for utilizing travel rewards, as well as suggest a strategy for beginners.

After that episode, I began lurking in travel hacking groups on Facebook and absorbing as much information as I could from websites such as,, and just to name a few. I signed up for free courses, and a friend even mailed me a book to help me learn.

I was sold on the idea. I knew I could do it and do it well. Being only months away from becoming mortgage free and therefore 100% debt free, we had big dreams of saving more than 60% of our take-home pay to snowball the future purchases of free and clear rental properties, and if we wanted our dreams of traveling the world to come true without sacrificing chunks of our savings, I knew earning and redeeming travel rewards would be the way to do it. I hadn’t had a credit card since I was 18 and was a little freaked out by the idea of signing up for one, but I knew I was ready to overcome that decade-old fear.

My very risk-averse husband, on the other hand, was not as certain. It took multiple conversations over several months, but he finally agreed to let us try it out. Now, a year and a half later with our first travel hack successfully booked, I asked him how he feels about travel hacking. His answer, “It’s pretty cool.” (Anyone else out there married to a man of few words?)

What systems do we have in place?


Meeting the spending limit within the allotted time frame can be difficult when living frugally, especially when the limit is $4,000 or $5,000 in three months. We plan the opening of cards with larger spending limits around large purchases, such as buying tickets for the FIFA World Cup last year and home updates that we did this year. We also change all of our automatic bill payments to use the new card, and we use the card for every single purchase possible until the spending limit is met.

I have a spreadsheet dedicated to staying organized with my credit cards, especially when we have a new spending limit to meet. Each time I open a new card, I dedicate a new tab to that card. I list the following information for the card on each tab:

  • Date of approval (the clock starts on the date you’re approved, not the date you receive or activate the card!)
  • Amount of sign-up bonus points
  • Amount of spending limit
  • Spending limit timeline
  • Annual fee
  • Current amount of points
  • A running sum of our current amount spent. I keep a log of each transaction amount until the spending limit is met.

Having & Sticking to a Zero-Based Budget

Overspending in order to earn credit card points is not winning the travel hacking game. As I just mentioned, my husband and I live pretty frugally right now in order to save for our future goals, and to make sure we’re not overspending, we put together a zero-based budget at the beginning of each month. I maintain this budget every weekday thereafter by balancing it against our transactions and adjusting the amounts allocated to our chosen categories as needed.

While we may go over budget in a category, we rarely go over the $2,400 we base our budget on each month. If we overspend in a certain category, we then have to choose which category doesn’t get as much money as we originally planned.

To view our budget, click here. This is our real, live budget and includes three groups – bills, sinking funds and spending. If you like the way it’s laid out, you can also save a copy of the free template and customize it how you wish!

Sinking Fund for Annual Fees

Good travel rewards cards come with annual fees, and that’s okay with me. I’ll gladly accept the difference of $905 that comes from paying a $95 fee upfront for $1,000 worth of free travel three months later, which is what we did with the Chase Ink Business Preferred card that I’ll tell you about in a little while.

As with all bills that we pay once per year, we divide this fee by 12, which is $7.92, and we contribute this amount each month to our “Annual Funds” sinking fund. The money dedicated to this sinking fund is kept in a savings account at our local credit union, and when it comes time to pay the fee, we just transfer the $95 from that account to our checking account, then make the credit card payment for it.

If you’re unfamiliar with sinking funds and are intrigued by the idea, check out this post that I wrote a couple years ago that goes into much more detail about them.

Paying in Full & On Time

If you’re paying interest to the credit card provider, they’re winning. You have to make sure you have the discipline to pay in full and on time no matter what.

My husband and I used a free third party service to clear our card balance every two weeks during the majority of the time we’ve had credit cards. This service, Debitize, would take each transaction amount from our checking account the next weekday morning, hold that money in a reserve account, then pay off the card every two weeks. Debitize has since been bought by another company and is no longer operating in that form, but if you want more information about how it worked so that you can see if you might be interested in a similar service, you can check out my three month review here. I have downloaded an app for another company that seems to offer the same service, but they are still working on adding our credit union. I’ll let you guys know if and when it works out!

For now, I pay off each card that has a balance every weekday when I’m balancing our budget. I simply cannot stand seeing more money in our checking account than we actually have (which is why I loved Debitize so much), so even if the balance is a dollar for a candy bar I bought the previous day, I’m paying it off. Doing this keeps me from feeling behind, which leads to me feeling in control and on top of our finances.

Some people clear their credit card balance each week, every two weeks or even just on the due date each month. Do whatever works for you – just make sure you’re never late and never pay interest.

Now that I’ve told you a bit about travel hacking, why wanted to start doing it and some of the systems we use, I want to share my reasoning for starting off with Chase cards, the type of rewards we earned and redeemed for our first hack, as well as how we used each card.

Chase Ultimate Rewards

Why Did We Start with Chase?

Remember that ChooseFI podcast episode I mentioned? Yep, that episode alone is why I chose to start out with Chase cards. I’m a faithful fan of Brad and Jonathan and trust them when they offer suggestions, so after listening to that episode, I decided that if I could get Ron on board, I would follow the strategy they suggested for beginners.

The Chase Gauntlet Strategy

Chase has what is very commonly referred to as the “5/24 rule.” What this rule entails is that Chase will automatically decline you if you have opened five or more personal credit cards issued by any bank in the last 24 months. Because of this rule, ChooseFI recommends starting out with Chase before any other bank, and in that episode, they list a sequence of suggested cards to open.

My First Two Cards

Being so new to credit cards, I was grateful to have a suggested plan, so I rolled with it. I started with the Chase Sapphire Preferred in December 2017, then the Chase Ink Business Preferred in February 2018. I earned a total of 130,000 Ultimate Rewards points (~$1,625 worth of travel) in signup bonuses alone from these two cards. You can learn about the signup processes and more about my reasoning for choosing these cards by reading the blog posts I wrote after I signed up for each one:

It has now been 17 months since I took out that first card. I have only signed up for three more cards since then, all of which are Chase and only two of which are personal cards, so I haven’t and won’t run into any issues with the 5/24 rule any time soon.

What are Ultimate Rewards?

Chase’s Ultimate Rewards program is a highly valuable and flexible transferable points currency. In addition to the ability to transfer points to several airline and hotel partners, Chase provides its own travel portal, which allows you to not only book flights and hotels but cruises, car rentals and experiences too.

Ultimate Rewards points are valued at 1.25 cents per point when redeeming them through Chase’s travel portal. This means that in addition to receiving free travel for money you would have spent anyway, you also get a 25% discount on that travel. The points may be worth even more when transferring them to one of Chase’s travel partners.

There are currently three Chase cards that offer Ultimate Rewards points that are transferable to travel partners:

The points from these cards, as well as from Chase cards that earn non-transferable Ultimate Rewards points, can also be combined. This is done by sending points in the amount of your choosing to another one of your eligible cards.

I transferred the points I earned on my Chase Ink Business Preferred card to my Chase Sapphire Preferred (I could have transferred to and from either card) so that all my points were together in one place when booking our flight and hotels. You can also transfer Ultimate Rewards points to an account belonging to a member of your household, or in the case of business cards, a fellow owner of your company.

How Did We Use Our Cards to Earn Points?

As I mentioned earlier, we put every single transaction possible on each new card until each spending limit was met. Afterwards, we chose the card based on which one will give us the most bang for our buck for the specific type of transaction.

We use the Chase Sapphire Preferred (which I will refer to as CSP) at restaurants since we earn double the points per dollar spent, and we use the Chase Ink Business Preferred (which I will refer to as CIBP) for our internet, phone and some business expenses since we earn triple the points for each dollar spent. Plus, my cell phone is insured by this card since we use it to pay the bill. And while the CSP doubles the points for travel purchases, the CIBP triples the points, so it is the card we choose to use for this purpose.

Other than having our phone and internet auto-paid with the CIBP, this card didn’t get much use along the way. I had the CSP connected to the free service, Debitize, that I mentioned earlier, so it was easiest to use it for everyday purchases. The CIBP was mostly used for larger purchases that required money to be transferred to our checking account from sinking funds.

There are numerous ways to optimize points per purchase, and some people get pretty fancy with this. For example, since the CIBP gives five times the points per dollar spent at Staples, there are people who buy gift cards for other retailers there to maximize the points on purchases they plan to make anyway. I haven’t done anything like this (yet), so I don’t have any experiences to share, but there are plenty of resources online that you can check out if you’re interested in this.

These two cards also come with referral links that friends can use when signing up for the cards. The referral bonus for the CSP recently increased, so if a friend uses your link to fill out the application for the card and is approved, that’s 15,000 extra Ultimate Rewards points for you, for up to 75,000 extra points per year. The same goes for the CIBP, which gives 20,000 extra points per approval for up to 100,000 extra points per year.

Hopefully I’ve covered all you need to know about the concept of travel hacking and Chase Ultimate Rewards points. So let’s talk about Greece!


Why Greece?

You may have noticed at the beginning of this post that I mentioned my husband got to choose our destination. I’ve actually received some pretty snarky messages on Instagram when I’ve mentioned this without providing more context. But it’s true, I had no idea where we would end up going for our very first travel hack.

As we got closer to paying off our house, we began talking more about what we wanted out of our upcoming debt free life, and we decided to take at least one major vacation each year. And since I knew Ron would just agree to go anywhere I wanted to go, I suggested that we take turns choosing the destination each year from there on out. Since it was 2018 and I had always dreamed of sitting in the stands at the FIFA World Cup, this new tradition started off with my pick, and off to Russia we went.

I started bugging Ron about his choice as soon as we got back from Russia at the very end of June, but it wasn’t until Christmas night that he surprised me with his decision by announcing our destination to the debt free community of Instagram. I couldn’t have been happier with his choice!

When I began writing this post, I asked him why he chose Greece, and in typical Ron fashion, he shrugged and responded, “I don’t know, it looked cool.” So there you have it!

We quickly decided to go for two weeks, just like we did with Russia, so that we could experience it without feeling rushed. Spending time in Athens was a given, so from there, we just needed to figure out how many islands we wanted to visit in the remainder of that two week time frame. We ended up settling on three islands so that we could have three days in each island and four days in Athens.

That left Ron with the decision of which three islands we would visit- after all, this is his trip – and he took a few days to think about it before deciding on Crete, Rhodes and Santorini.

Figuring out when we wanted to go was a little more difficult. We knew we wanted to avoid the super busy tourist (and hot) season, but we also knew that many of the businesses close in the off season. In the end, we finally chose the last two weeks of September, the 16th through the 29th. We chose these two specific weeks for two reasons – the ocean would still be warm from heating up all summer, and more importantly, UT has an away game followed by an off week for the two Saturdays we’re gone.

I hope you’re not bored by me taking the time to explain the reasoning behind these decisions, because I’m telling you all of this for a reason. Saving money in the form of redeeming the least amount of points possible or by trying to avoid paying any cash was never a factor when choosing our destination, sub-destinations, length of the trip or travel dates.

I’m sure we could have saved a lot of points for future use by factoring in cost when planning, but it was more important to us to do exactly what we wanted and when we wanted. I’ll talk about this a little more in a few minutes.

Below is the basic itinerary of our trip if you’re interested. It just shows flights and hotels, because we don’t pre-book activities; we prefer to explore and wing it while on vacation!

Sunday, September 15

  • ✈️ Depart Atlanta 3:15 PM
  • ✈️ Arrive in Chicago 4:14 PM
  • ✈️ Depart Chicago 5:25 PM

Monday, September 16

  • ✈️ Arrive in Athens 11:45 AM
  • ✈️ Depart Athens 4:00 PM
  • ✈️ Arrive in Crete 5:00 PM
  • 🏨 Check into Hotel in Heraklion

Tuesday & Wednesday, September 17-18

  • 🌄 Fun in Crete

Thursday, September 19

  • 🏨 Check out of hotel
  • ✈️ Depart Crete 11:20 AM
  • ✈️ Arrive Athens 12:10 PM
  • ✈️ Depart Athens 1:10 PM
  • ✈️ Arrive Rhodes 2:10 PM
  • 🏨 Check into hotel in Rhodes

Friday & Saturday, September 20-21

  • 🌄 Fun in Rhodes

Sunday, September 22

  • 🏨 Check out of hotel
  • ✈️ Depart Rhodes 9:50 AM
  • ✈️ Arrive in Athens 10:50 AM
  • ✈️ Depart Athens 1:30 PM
  • ✈️ Arrive in Santorini 2:25 PM
  • 🏨 Check into hotel in Firostefani

Monday & Tuesday, September 23-24

  • 🌄 Fun in Santorini

Wednesday, September 25

  • 🏨 Check out of hotel
  • ✈️ Depart Santorini 11:55 AM
  • ✈️ Arrive in Athens 12:50 PM

Thursday-Saturday, September 26-28

  • 🌄 Fun in Athens

Sunday, September 29

  • 🏨 Check out of hotel
  • ✈️ Depart Athens 11:35 AM
  • ✈️ Arrive in Philadelphia 3:50 PM
  • ✈️ Depart Philadelphia 6:15 PM
  • ✈️ Arrive in Atlanta 8:47 PM
  • 🏨 Check into hotel in Atlanta

Monday, September 30

  • 🏨 Check out of hotel
  • 🏠Head home

Alright, let’s talk points.

As a reminder, the two cards we used to earn the points redeemed for this trip are listed below.

Points Breakdown


All of the flights that we booked are economy. After the 10 hour flight from Toronto to Istanbul last year, we definitely considered booking at least Premium Economy seats for our long round trip flight from Atlanta to Athens. However, after looking at the major increase in points that would be required, we decided pretty easily that we just don’t care enough about that aspect of travel right now to justify using the extra points.

Our trip contains a total of five flights, three of which were booked with points. The amount of points and equivalent dollar amounts listed are totals for both of us together, so just divide them in half if you’re looking to get an idea of the cost for a single passenger. Dollar amounts listed are US dollars.

  • ATLATH (Round trip)
    • Date Booked: 2/9/19
    • Class: Economy
    • Airline: American Airlines
    • Points: 162,732
    • Equivalent Dollar Amount: $2,034.16
  • ATHHER (One way)
    • Date Booked: 3/17/19
    • Class: Economy
    • Airline: Sky Express
    • Points: 16,118
    • Equivalent Dollar Amount: $201.48
  • ATHJTR (One way)
    • Date Booked: 3/19/19
    • Class: Economy
    • Airline: Sky Express
    • Points: 22,209
    • Equivalent Dollar Amount: $277.62

Flights Total

  • Points: 201,059
  • Equivalent Dollar Amount: $2,513.26
  • Value per Point: 1.25 Cents


We selected nice hotels for this trip – not super luxurious, because that’s just not our style – but very nice. One of the hotels is all-inclusive (our first ever!) and only one of the five rooms we booked is a standard room. The most important factors to us were location, the view and the quality of service. We used TripAdvisor when choosing all of our hotels.

And interestingly enough, the only little tiff that Ron and I had during the entire process of booking this trip was when it came to our very last hotel – the one we booked for one night in Atlanta since our flight gets back so late. I didn’t need anything more than a bed and wanted to conserve as many leftover points as we could, but Narcotics Detective Mondelli has much higher concerns and standards than I do. We ended up compromising by staying in a nicer hotel than I thought necessary, but not in as nice of a part of town as he thought necessary.

  • Heraklion, Crete
    • Date Booked: 3/17/19
    • Rating: 4 Stars
    • Room Type: Standard
    • Number of Nights: 3
    • Points
      • Per Night: 10,588
      • Total: 31,764
    • Equivalent Dollar Amount
      • Per Night: $132.35
      • Total: $397.05
  • Rhodes, Island of Rhodes
    • Date Booked: 3/19/19
    • Rating: 5 Stars (All-Inclusive)
    • Room Type: Sea View (Upgraded)
    • Number of Nights: 3
    • Points
      • Per Night: 16,838
      • Total: 50,515
    • Equivalent Dollar Amount
      • Per Night: $210.48
      • Total: $631.44
  • Firostefani, Santorini
    • Date Booked: 3/19/19
    • Rating: 4 Stars
    • Room Type: Sea View (Upgraded)
    • Number of Nights: 3
    • Points
      • Per Night: 20,395
      • Total: 61,185
    • Equivalent Dollar Amount
      • Per Night: $254.94
      • Total: $764.82
  • Athens
    • Date Booked: 3/19/19
    • Rating: 5 Stars
    • Room Type: Acropolis View (Upgraded)
    • Number of Nights: 4
    • Points
      • Per Night: 19,478
      • Total: 77,911
    • Equivalent Dollar Amount
      • Per Night: $243.47
      • Total: $973.89
  • Atlanta, GA
    • Date Booked: 3/24/19
    • Rating: 2 Stars
    • Room Type: King Bed (Upgraded)
    • Number of Nights: 1
    • Points: 9,687
    • Equivalent Dollar Amount: $121.09

Hotels Total

  • Nights: 14
  • Points: 231,062
  • Equivalent Dollar Amount: $2,888.29
  • Value per Point: 1.25 Cents

The combined total of points redeemed and equivalent dollar amount for the flights and hotels is below. By the time we finished booking everything, we had 441 Ultimate Rewards points left for future use.

Flights & Hotels Total

  • Points: 432,121
  • Equivalent Dollar Amount: $5,401.55
  • Value per Point: 1.25 Cents

Out of Pocket Costs

We wouldn’t have splurged nearly as much for this trip (and would have especially put much more consideration into the hotels we chose) if we had paid for it all in cash! But that was the awesome thing about using points – it enabled us to indulge without having to factor in any opportunity costs. With that being said, there were and will be some out of pocket costs.


As I mentioned a few minutes ago, there were two flights that we had to pay for because flying to or from the island of Rhodes turned out to be impossible for me to figure out how to hack. I checked back time and time again, but there were no options to or from Rhodes through Chase’s travel portal. I even called one of their extremely friendly travel representatives who apologized profusely that she couldn’t help me. I couldn’t figure out any way possible to transfer Ultimate Rewards points to Olympic Air either, so finally we just said forget it and paid cash.

Flights are definitely not the only option for travel between the Greek islands, but they’re the fastest. Taking ferries would have been cheaper, but we were constantly on the go during our last vacation and spent several nights on trains, and for this trip we just wanted to relax and utilize our time as best as we could.

  • HERRHO (One way)
    • Date Booked: 3/17/19
    • Class: Economy
    • Airline: Olympic
    • Total Cost: $291.38
  • RHOATH (One way)
    • Date Booked: 3/19/19
    • Class: Economy
    • Airline: Olympic
    • Total Cost: $231.11

Flights Total: $522.49


Below are the on-site fees for the hotels in Greece that Ultimate Rewards points would not cover.

  • Heraklion: $10.19 (Tourism Fee)
  • Rhodes: $61.18 (Tourism Fee + Cash Deposit)
  • Firostefani: $10.22 (Tourism Fee)
  • Athens: $18.17 (Tourism Fee)

Hotels Total: $99.76

Annual Fees

We cannot forget about the annual fees we paid for the two cards we used to earn these points! For context, I am currently on my second year with both cards.

  • Chase Sapphire Preferred: $95 (The fee was waived the first year)
  • Chase Ink Business Preferred: $190

Annual Fees Total: $285

Spending Money

I’m not going to include this amount in our total out of pocket costs since it’s not feasible that points could cover the spending money we’re allocating for the trip, but I wanted to share in case anyone was curious.

It was our turn to claim my stepdaughter on our taxes this year, so we received about $1,800 back. $1,500 of that has been set aside as spending money for the trip. We will use our credit cards for most of the transactions and have not yet talked about how much of this amount we will take in cash.

However, we do not set or follow a budget when we go on vacation. If we end up spending more than we set aside, we will just pay for it when we get back. That’s one of the many perks of being completely debt free and living on less than half of your income!

Below is our total out of pocket cost between flights, hotels and annual fees.

Out of Pocket Costs Total: $907.25

Trip Totals

  • Points: 432,121
  • Dollar Equivalent of Points: $5,401.55
  • Out of Pocket Costs: $907.25
  • Total Trip Value: $6,308.80
  • Percentage of Trip Covered by Points: 86%

Not bad, right? I have no problem paying $907 for a $6,309 trip of a lifetime!

I’m sure there are plenty of ways that we could have better optimized our points for this trip, but I consider our first hack to be a success! This trip will be our three year wedding anniversary celebration, as well as a celebration of hitting the one-year/$50,000 checkpoint of our current two-year/$100,000 savings goal (read more about our current goal here), so I am glad that we went big for it instead of trying to conserve points.

I hope I covered every single question you guys may have about our very first travel hack, but just let me know in the comments below if there is anything I didn’t touch on.

Thank you all so much for following along this new venture of travel hacking over the past year and a half! I can’t wait to plan our next hack and share all the details with you!

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  1. […] hotels and most of the flights, we got those for free using Chase Ultimate Rewards points! Click here to read […]

  2. Curtis says:

    Hello!! My wife and I are really liking your blog and the detail of it so we can “picture ourselves” doing similar things. I am trying to figure out/calculate how you were able to obtain over 400,000 points from just 2 credit cards? Were the points structures just that good back in 2017? Or did you open both cards for both you and your spouse? Thanks in advance for your reply.

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