This happens LITERALLY every year! The SSA is the most dysfunctional agency in government. Last year they sent my 1099 to my old address even though I had updated my information TWICE with them. The year before they had the wrong SSN printed on my form!!! I've learned to just file an extension automatically every year because something always goes wrong with these forms. And yes, I'm still waiting for mine this year too.

Update: I took the advice about requesting a replacement through the online portal, and it worked! Both our 1099s were available to download within 48 hours of making the request. For anyone else still waiting, definitely try the replacement request option instead of just checking for the original. Thanks everyone for your help!

Thanks everyone for the helpful replies! I'm going to gather my DD-214, recent W-2s, and tax returns from the last few years. I'll also prepare a list of my employers for the past 15 years and make sure my bank account info is handy for direct deposit. I'm a bit worried about the phone system issues some of you mentioned. I might try the online application instead, but I have a few complicated questions about my pension that I was hoping to discuss with a representative. I'll definitely get confirmation numbers and names for everyone I speak with. And I'll decide on the tax withholding beforehand - probably going with 10% federal withholding to be safe.

Just thought of something else - if you're planning to continue working, make sure you understand how your earnings might increase your future benefit amount. Even after you start receiving benefits, SSA will automatically recalculate your benefit amount annually if your recent earnings are higher than one of the 35 highest years used in your original calculation. And since you mentioned being a veteran, be sure to check with the VA about any additional benefits you might qualify for. Many veterans don't realize there are pension benefits available through the VA that are separate from Social Security.

I'm surprised no one has mentioned that you should make an appointment at your local SSA office. While getting someone on the phone is difficult, in-person appointments can be scheduled online. I found it much more helpful to sit down with someone who could look at all my options. For survivor benefits, they often prefer to handle these cases in person anyway. When my sister was widowed, she tried doing everything by phone and ended up with incorrect information.

Thank you all for the helpful information. I think my best strategy is to take the reduced survivor benefits now since I need the additional income, and then switch to my own retirement benefit when I reach FRA. I'll try to get an appointment at the local office and also check out that Claimyr service to speak with someone sooner. I definitely want to make sure I understand exactly how much I'll receive and how my part-time work will affect things before making any decisions. This community has been so helpful!

Update: I should have mentioned that for self-employment income specifically, there's a lag time because the SSA doesn't receive your earnings information until after you file your tax return. If you filed extensions, this could delay the AERO process. For complicated cases like yours with both WEP and ongoing self-employment, it's best to speak directly with a Technical Expert (TE) at SSA, not just a regular claims representative. When you call, specifically request to speak with a TE who specializes in WEP calculations.

IMPORTANT QUESTION: Are you also subject to GPO (Government Pension Offset)? That's different from WEP and applies to spouse/survivor benefits. The combination of WEP and GPO can be really complex. Just making sure you're aware of both if they apply to your situation.

@casual_commenter - Yes, Claimyr absolutely works. My call was connected to SSA in under 15 minutes after trying for days on my own. Saved my sanity during my disability application process.

@OP - Regarding your question about your Quebec marriage certificate being in French and English: The English portion should be sufficient for SSA purposes. However, if the certificate is predominantly in French with just some English elements, having a certified translation ready might save time. SSA may accept it as is, but they could request a translation if they have difficulty verifying details. Also, since your wife worked in a non-covered position (teacher's aide in a district not participating in Social Security), she may be subject to the Windfall Elimination Provision (WEP) or Government Pension Offset (GPO) if she receives a pension from that employment. This could affect both her own benefits and any spousal benefits. Be sure to mention this when applying.