Maximize Your Delta Experience: Unlocking the Potential of Amex Miles Headstart Program

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Similar to the recently discontinued Marriott Points Advance, Delta offers its own program that allows booking an award flight without having all the necessary miles available. The program is called Amex Miles Headstart. In essence, if you find a Delta flight with a low award price and you don’t have enough miles to book it, fearing the deal won’t last, all is not lost: you can advance Delta miles.

How it Works

When you’re ready to book an award ticket and need an advance on Delta miles, follow these general steps:

  • Check how many miles you are eligible to receive in advance by requesting Miles Headstart.
  • Choose the number of miles you’d like to receive, and they will be deposited into your Delta SkyMiles account.
  • You will have 6 months to earn this amount back using your Delta SkyMiles Card.

There is no fee for this feature.

Additionally, if you have a Delta Amex, you also get:

  • 15% discount on your award ticket prices
  • $100 Delta credit when you spend $10,000 (on top of the SkyMiles you normally earn)

What’s the Catch?

While there isn’t a catch per se, there are a few things to be aware of:

  • Although there is no fee for this feature, if you do not earn the advanced amount of miles back in 6 months, you’ll be charged 2.5 cents per unearned mile.
  • Miles earned from flying do not count toward the Headstart balance.
  • Only miles earned from the same card associated with the Headstart balance are counted toward the balance.
  • The number of miles deposited into a Delta SkyMiles account is limited to 60,000. This includes not only miles received from Headstart but also miles purchased and transferred into the account.

The Best Strategy to Earn Back Headstart Miles

Although only miles earned with your card count toward your Headstart balance, there are still creative and efficient ways to earn back the miles. Here are a few suggestions:

  • Use your card for everything: This is the most obvious and straightforward approach.
  • Use your card for bonus categories, where you earn 2x or 3x (e.g., dining, groceries, Delta purchases, etc.)
  • Take advantage of Miles Boost promotions.

Eligibility Requirements

Approval for this feature is determined on a case-by-case basis. Factors affecting eligibility include:

Practical Scenario

Let’s consider a practical scenario where you apply for and receive miles in advance but do not earn any of those miles back. For example, let’s say we plan to go to Calgary. One non-stop roundtrip economy flight from Los Angeles to Calgary would require 25,000 miles and $60.

If we were to advance all 25k miles and not earn them back, we would end up paying an equivalent amount of $685 (25,000 miles x 2.5 cents per mile + $60).

Alternatively, we could book the same flight with cash.The cash price appears significantly lower at $448.

A few things to note here:

  • Amex charges 2.5 cents per unearned mile remaining on your Headstart balance, which is substantially lower than the 3.5 cents you would pay if buying miles directly from Delta.
  • The comparison was made for the same flight with the lowest award price and then compared to the cash ticket price for the same flight, dates, and times. This might not be fair since award prices are not bound to cash prices; therefore, there might be lower cash prices for slightly different dates/times.
  • When we tried to get an advance, we discovered that the available amount was only 6,000 miles, even though we use our Delta SkyMiles® Gold American Express Card pretty actively. This makes the example above somewhat theoretical since we wouldn’t be able to get the full amount needed for the award.

This reinforces the general consensus that “buying” miles doesn’t make financial sense and only makes sense when you are short a small amount for a meaningful redemption. So, if you do try Miles Headstart, make sure you take advantage of it and not the other way around.


Amex Miles Headstart feature seems pretty good when you’re short on miles and need to book an award ticket immediately, especially considering it is free of charge. Just make sure you don’t end up buying those miles, as even with a discounted price of 2.5 cents per mile, you’ll overpay significantly compared to the cash price. If you have tried Miles Headstart, feel free to share your experience.

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