Can I transit through the US before the trip whose details were used for an ESTA application?

Question

I am requesting an ESTA for the first time, for a trip due in September to the US. I'm thinking of doing it right now because I'd like to be sure about the outcome before booking my flights.

In the ESTA application, I'm going to provide point of contact and place of stay (and –I'm not sure yet whether this will be asked– trip dates) based on my September trip.

However, it is possible that I'll also need to take a connecting flight through the US in July (i.e. between now and September).

Should I:

• Request another ESTA for July (ticking the box "connecting through US" which disables the questions about points of contact)?

  But I worry that the ESTA previously requested for Semptember would get invalidated.

• Refrain from applying for the ESTA I need for September, and only request one for July?

  But I worry that it won't be then applicable in September, since I'll have ticked the box "connecting through US" rather than "short stay in the US".

• Use my ESTA requested for September as my only ESTA, and travel in July too?

  (I used this scenario for the question title)

• Take any other approach?

Answer 1

Request an ESTA for July now. Once you have an ESTA, you have an ESTA; it covers all trips to the US, not merely those with the same details as those you applied for in your first trip.

If you don't show up in July, and do show up in September, you will get additional questions but they won't be particularly suspicious questions. You have the ability to update some information in your ESTA, which will be limited if you had initially specified transit but that's apparently not a problem. See this question and this question for more details on that.