Quick Points: Short on Delta SkyMiles? Try Miles Headstart
Attention, Delta American Express cardholders: If you're short on Delta SkyMiles, you can now receive advanced miles. Known as Miles Headstart, this program from American Express could be just what you need to get your next redemption booked if you don't have enough SkyMiles in your account.
Not to be confused with Medallion MQD Headstart, Amex's Miles Headstart program is open to all eligible Delta Amex cardholders, such as those with the Delta SkyMiles® Gold American Express Card or the Delta SkyMiles® Platinum American Express Card.
Related: Best Delta credit cards
What is Amex's Miles Headstart?
Miles Headstart allows cardholders to receive an advance of SkyMiles to book their trip now. In essence, it is a short-term loan from Delta SkyMiles. Therefore, you will have to pay it back. You will have six months to spend the required amount on your card to not pay for the miles. If you don't spend the required amount, the remaining amount of SkyMiles will be charged at a rate of 2.5 cents per mile, much higher than Delta sells its miles.
There are some eligibility factors, and not everyone may be approved. According to Amex, if you are eligible for Miles Headstart, the maximum number of miles you can get in advance is based on several factors.
Per Amex's eligibility terms:
"You may have only one (1) Miles Headstart Balance outstanding at any time. The Miles Headstart Start Date is defined as the date that advanced miles are posted to your Delta SkyMiles account. The Miles Headstart End Date is defined as the last day of the sixth full billing period following the Start Date. If, on the End Date, there are miles remaining in your Miles Headstart Balance, then your Card account will be charged for those remaining miles at a rate of 2.5 cents per mile. The APR for this charge will be the standard purchase APR on your account, which varies with the Prime Rate. If you do not see the advanced miles posted to your Delta SkyMiles account immediately, please allow up to 72 hours. Any miles advanced cannot be returned or transferred and are subject to Delta SkyMiles terms and conditions."
Things to note
You have six months to earn the miles back by spending on your Delta American Express card. If you do not spend the amount required to earn the miles back, you will be charged 2.5 cents per mile.
If you know you can spend the money required, this can be a great option, as you won't have to spend any extra money out of pocket and can lock in an award redemption before the rate changes.

As you can see, you will need to spend a very high amount on average every month to not owe anything. To "borrow" just 5,000 miles, you must spend over $5,000 to receive no additional charges. This average spending can be less if you spend more on categories like Delta purchases, as every card in the SkyMiles family earns at least 2 miles per dollar spent on all Delta purchases.
If you don't think you can spend this amount back in the six-month time frame, you might want to consider buying SkyMiles directly from Delta, as you'll be charged 3.5 cents per mile. For example, buying 6,000 SkyMiles costs just $210 compared to the over $5,000 you must spend on your card, bringing the Miles Headstart option's purchasing rate to roughly $1 per mile.
If you hold an Amex card that earns Membership Rewards points, you could always transfer those points to Delta since the airline is one of Amex's many transfer partners. Using transferable points is one of our favorite ways to add miles to your SkyMiles account.
Bottom line
Miles Headstart can be a great way to quickly get some extra Delta SkyMiles that you need to book your trip.
However, this option will require spending a lot on your card every month to earn the loaned miles back. If you don't think you can meet these spending requirements, you will be charged 2.5 cents per mile, much more than it would cost to buy SkyMiles directly from Delta or transfer Membership Rewards points from Amex.
If you don't think you can meet the spending requirement to earn the miles back within six months, consider purchasing the miles directly from Delta instead.
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