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Compensation when things go wrong

I'd like to hear about your experiences when award travel doesn't go as planned. I recently redeemed 176,000 Air France points to book a business class flight from Indianapolis to Biarritz, France for my sweet elderly mother. I knew it wasn't a good deal but it was the exact date she wanted, ideal layover times, and most importantly, I was able to book the entire trip on 1 record locator (The trip involved 2 stops in JFK and CDG, no way around it). I thought this would hold the airline accountable in case there were any delays. The first leg was on Delta metal, the rest on Air France. Low and behold, the delta flight from IND to JFK was delayed and was going to be an impossibly tight connection. Luckily, (or so we thought) a Delta agent in the lounge in IND rebooked my mom on the next AF flight, departing just 1 hour later. She even physically re-printed her boarding pass, we were thrilled that she was upgraded to La Premier, seat 1A. When she got to JFK, an extremely rude Air France lounge agent literally scolded my mom and told her the ticket wasn't valid. Air France took zero accountability, pointing the blame to Delta saying that they didn't issue the ticket properly. Long story short, she had to wait another 5 hours at JFK, and ended up flying on super old plane AND they lost her bags. Far from worth 176,000 points. What recourse do I have? I paid for the taxes and fees with my Chase Sapphire Reserve.

Compensation when things go wrong

I'd like to hear about your experiences when award travel doesn't go as planned. I recently redeemed 176,000 Air France points to book a business class flight from Indianapolis to Biarritz, France for my sweet elderly mother. I knew it wasn't a good deal but it was the exact date she wanted, ideal layover times, and most importantly, I was able to book the entire trip on 1 record locator (The trip involved 2 stops in JFK and CDG, no way around it). I thought this would hold the airline accountable in case there were any delays. The first leg was on Delta metal, the rest on Air France. Low and behold, the delta flight from IND to JFK was delayed and was going to be an impossibly tight connection. Luckily, (or so we thought) a Delta agent in the lounge in IND rebooked my mom on the next AF flight, departing just 1 hour later. She even physically re-printed her boarding pass, we were thrilled that she was upgraded to La Premier, seat 1A. When she got to JFK, an extremely rude Air France lounge agent literally scolded my mom and told her the ticket wasn't valid. Air France took zero accountability, pointing the blame to Delta saying that they didn't issue the ticket properly. Long story short, she had to wait another 5 hours at JFK, and ended up flying on super old plane AND they lost her bags. Far from worth 176,000 points. What recourse do I have? I paid for the taxes and fees with my Chase Sapphire Reserve.

Hilton

I made the mistake of getting the Hilton Honors card Hilton Honors Business card and the Aspire card before I knew anything about points and miles. Can you give me a strategy for how to close these cards and then reopen them so that I can book some of these amazing Hilton aspirational properties? After you have the cards & bonuses how do you continue adding to your Hilton points for future aspirational bookings since these properties cost sooooo many points?

KLM flights to Europe for big family

Flying my family of 7 to Europe summer 2026 and the taxes and fees for klm are high. Copenhagen to Vegas was $1,700 for my family of 7 and LAX to Barcelona is over $1,000 Just curious if you know of specific European cities where those fees are less? Also looking at virgin Atlantic but those fees are even higher. Still super affordable and seems like best option for low points but just wondering if I’m missing something - thanks!

Changes to Chase Sapphire Reserve

Could you do a deep dive into the changes to the CSR?

Emirate Biz for 69k?!

Am I thinking of this correctly, because I never hear anyone talk about how good of a deal this could be: If Emirates economy ticket is 30,000 pts and costs 39,000 points to upgrade (based on availability ), you could be getting an Emirates biz class ticket for just 69k instead of the saver biz fare of 87k. Of course this would be based on availability, and a biz class ticket might not be able. Am I mistaken on this? I’m wanting to go to Italy next summer and hoping to fly my first biz class ticket on Emirates, but of course want to save as much points as possible.

Credit scores

Can you please explain the rationale to freezing your credit score with the top credit bureaus prior to applying for a card?

Individual night bookings

When you book an each night individually for a trip, does the hotel combine the reservations so that you stay in the same room for the duration or is there a chance you’d have to move rooms throughout your trip?

AMEX

I got an Amex gold personal in 2022 (I think) before really understanding points. I downgraded it to the free Amex everyday card maybe last year to avoid another fee. Now I kind of want the Gold back for the multipliers because I’m starting to get into Hilton. Do I have any options? Seems like Amex is an easy way to get Hilton points, which cards would you recommend?

Cards that are going away

Lately I’ve seen more and more posts about cards that are potentially going away so we should apply for them now to earn the Subs. Can you go over these cards? I know Hawaiian and American Citi cards are brought up often. I feel like I need to get something before it’s gone forever but I’m stressed about the options!

How does the Capital One Spark card work?

I scooped up the Spark when I had a big spend, but now I realize the points aren't transferable? Do I need to get another Cap1 card to make it work?

New Chase $10 monthly Lyft benefit

Do you have any suggestions on how to use this monthly benefit when you don't generally need to use Lyft?

Time Between Personal and Business Card Applications

Is the amount of time you wait between personal card applications and business card the same? Or would you wait less time between business credit card applications?

Amex transfer to Hawaiian Airlines change

Hi TMS. As Amex no longer allows to transfer Amex points to HawaiianMiles as of June 30th, do you recommend speculatively transferring Amex points to HawaiianMiles now to take advantage of great options when booking with Alaska Airlines? Thank you!

upgrades at gate or app

Can you go into detail on how to ask at the counter for upgrade options such PE to Business on KLM/Airfrance? Is best to do thru the app at checkin time or wait to get to the airport?

Sharing business class seats

Alex mentioned on their flight to Amsterdam her family had two business class seats that they kind of took turns with. Is this something that is acceptable with other airlines or would you potentially get in trouble? It is hard to get more than 2 business seats on many international flights. For example, if I booked JAL and I had 2 business seats and 2 PE seats for my family of 4, would we be able to switch halfway through the flight?

Citi AA Double Dip Status Update

Could you give us an update on the Citi AA Biz card double dip strategy?

Info on P2 apps

What email/phone numbers do you put on P2 apps if you are a P1 who manages everything?

Amex Retention offer with intent to downgrade

I have an Amex business platinum card that I’d ideally like to downgrade to an Amex biz green when my AF comes due. If I’m offered a retention offer, is there a way to downgrade after meeting that offer requirement (or sooner) or do I need to wait a year before downgrading? Thanks!

How would your strategy change if you were ONLY using personal cards?

I know y'all love a good business card, but I'm curious how your strategy would change if you were just starting out and personal cards were the only option. After the classic "beginner cards" of CSP and Capital One Venture, what would you focus on? Thanks!

Capital One Card Quantity Limits

I have heard you guys mention that capital one only allows you to have two personal cards at a time. My question is whether that has any caveats, such as if you’ve had one of their cards for more than 7 years if you might be able to have more than two? My oldest card is a Capital one, so I never want to close that, but I’d like a Venture X as well, and have heard you say I don’t really want to cancel that either. Are my Capital one points earning opportunities pretty limited, then?

How far in advance do you book SLH properties?

We are wanting to stay at the Grand Hotel Lake Como property in 2026. I have all the points ready to go but the calendar isn’t open for cash or points. How do you figure out when the rooms will be open for you to book in order to snag availability? I noticed lots of SHL properties weren’t available for 2026 yet (ex Santorini)

Bora bora

Planning a trip here in a few years so mostly in the points earning/planning stage. I’ve been looking at award availability about a year out (just to practice seeing what comes up) and it seems like Conrad Bora Bora drops availability randomly. There’s more availability closer out than planning a year out. With flights on Air Tahiti Nui I’ve found some business class flights 10-11 months out but random dates. It seems United releases a few business class awards closer towards the date of flying. Tips on booking flights vs hotel first for this kind of trip?

Paying for College with Credit Cards

I am paying for my grandson's college. The college charges a 3% fee for using a credit card for tuition and fees. Is it still worth it? Is there any workaround to it? What is the best utilization of ccs to do this? It will be about $35k each year for five years. Hoping that I will have enough points saved up at the end of five years to take him on an amazing graduation trip using points!

Amex business plat airline incidental credit

What are the best ways to use this credit? I’ve seen some data points online to suggest cheap (<$100) flights might qualify. I’ve also heard you all talk about the United travel bank. What are some easy ways to not miss out on this credit, esp if there’s no incidental charges coming up?

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