When to apply for Social Security if retiring at 65? Need payment timing advice to avoid income gap

You're right about SS payments coming in the month after they're due. If you want your payments to start for July, you'll receive that payment in August. If you apply for June, you'll get that payment in July. BUT - important to know that any earnings you have in June count toward the annual earnings test if you're below your Full Retirement Age (which at 65, you are). You might want to check if you'll be over the earnings limit for 2025, which could reduce your benefits temporarily.

I was in EXACTLY the same situation last year except I turned 66 in August! Applied for benefits to start July 1st after retiring June 30th. Got my first payment August 3rd and it worked out fine. Had to use a bit of savings to bridge the gap but wasn't too bad. But make sure you apply 3-4 months BEFORE you want benefits to start!!! They take forever to process applications these days!!

To directly answer your question: if you want your first SS payment to arrive in July (to minimize income gap), then yes, you need to apply for a June benefit start date. However, there are several factors to consider: 1. The annual earnings test for 2025 is projected to be around $22,320 for people below FRA. If you earn over that amount before reaching FRA, SSA withholds $1 for every $2 you earn above the limit. 2. Your Full Retirement Age is 66 and 10 months (assuming you were born in 1960). By claiming at 65, you're taking about a 13-14% permanent reduction in your monthly benefit amount. 3. You can apply up to 4 months before you want benefits to begin. I'd recommend applying in March for a June or July start date. 4. Consider whether you have enough savings to bridge a one-month gap versus the permanent reduction for claiming early.

I had the WORST experience trying to time this last year. Applied for my benefits 3 months before retirement but SSA lost my application!!! By the time I figured out what happened I had to wait 3 extra months with NO income!!! It was a nightmare dealing with them on the phone too - calling and calling and never getting through. 😡

hi there just my two cents but dont forget about the 8th of the month rule!!! ss pays people based on birthday - if ur born 1st-10th u get paid on 2nd wednesday, 11th-20th is 3rd wednesday, and 21st-31st is 4th wednesday. only exception is if u also get ssi then its always the 1st. so when ur trying to plan for the gap remember ur actual payday might be middle or end of month

I think u should just apply for July 1 benefits. That way you don't have to worry about any earnings limits or complications. Yes you'll have a gap between last paycheck and first SS check, but that's normal. Most people have to deal with it. Maybe see if your employer will pay out any vacation days you have left to help bridge the gap?

Do you have a 401k or IRA? You could take a small distribution from that to cover the gap month. That's what my brother did. Just make sure you understand the tax implications.

Based on what you've shared, I recommend applying for benefits to start in July. Here's why: 1. You'll exceed the 2025 earnings limit by June, which would mean SSA would withhold some of your benefits anyway 2. The withholding could get complicated and potentially cause overpayment issues later 3. A one-month gap is manageable with some planning (vacation payout, small retirement account distribution, or savings) I'd suggest applying in March (4 months before) to ensure everything is processed in time. Also, remember that your first payment for July benefits would arrive in August, likely on the 3rd Wednesday based on your July 15th birthday.

One more thing to consider - if you're enrolling in Medicare at the same time, that starts the first day of your birthday month (July). So if you apply for both SS and Medicare together in March, your Medicare will begin July 1 regardless of when your SS benefits start. Just something to keep in mind for your overall retirement transition planning.