Following up on my question earlier today: "Can I Claim Retroactive Spousal Benefits Based On A Restricted Application And Later Claim My Own Benefits Retroactively?" (Thenk you for that answer)
Would my strategy work if I filed in two different month rather than the same month (June and July). I would then pay back my Dec. HSA contribution so I'm clear on the 6 month rule.

If I call SS on July 1 to apply for my benefits to begin that same month, will they?

Hi. You can apply in June 2021 and claim benefits retroactively to as far back as December 2020, but I don't know what effect that would have on your HSA options. HSAs are regulated by the IRS, and my expertise is limited to Social Security benefits.

I'm assuming that your own benefit rate is higher than your spousal rate. If that's the case, you'll want to claim your own benefits effective with January 2021 if that's the month you reached age 70. You could apply anytime between now and July 31 2021 and claim your benefits effective with January 2021. You could also file a restricted application for spousal benefits as soon as today (i.e. April 26 2021) and claim spousal benefits retroactively as far back as October 2020, but again I don't know what effect that would have on your the HSA contributions you made in those months.

The bottom line is that for any months you end up being entitled to both spousal benefits and your own benefits, you can only be paid the higher of the 2 benefit rates. You can't get extra benefits by filing for one type of benefit first and then claiming a different type of benefit retroactively for the same months if that's what your plan is. If you claim spousal benefits first and then you later apply for your own higher benefits retroactively for any months that you've already been paid spousal benefits, Social Security will simply withhold the amount of spousal benefits paid for those months from your back pay.

For example, say Bob files in April 2021 for spousal benefits retroactive to October 2020. Bob's spousal rate is $1000, so he receives a back payment of $6000 for October through March 2021. Bob then starts getting his regular monthly spousal benefit payments in May (for April). In July 2021, Bob applies for his own benefit rate of $2000 retroactive to January 2021. Social Security would withhold from Bob's back pay the amount that he was already paid as a spouse for the overlapping months. So, instead of getting $12000 in back pay for January through June, Bob would only get $6000 since he was already paid $1000 for each of those months in the form of spousal benefits. However, the $3000 in total spousal benefits that Bob was paid for October thru December 2020 would not be withheld from his back pay because Bob wasn't entitled to his own benefits for those months.

Whenever you apply for your benefits it's going to take Social Security an indefinite amount of time to process your claim to the actual payment of your benefits. And, if you file for spousal benefits first it will likely take Social Security longer to process your subsequent application for your own retirement benefits. I don't know what Social Security's processing times are looking like these days, so you might want to direct your last question to them.

Best, Jerry