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Social Security Has a ‘Maddening’ New AI Phone Bot. Here’s How to Deal With It

Posted on May 29, 2025

Social Security’s new phone bot can be frustrating to use. Here’s how to navigate it. 

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The Social Security Administration’s new AI-powered phone bot is coming, whether you’re ready for it or not — and apparently whether it’s ready or not, too. Reports out in recent days indicate that the system has been struggling to handle seemingly simple tasks for people calling in with questions. 

I’ve been covering Social Security for some time now, so I’m well aware of the challenges confronting the agency, including severe layoffs, and how those challenges affect the more than 70 million people currently receiving Social Security benefits. I’ve called the agency myself multiple times to see how it’s responding, or failing to. 

In the last few days, I’ve put the AI phone bot to the test, and far too often, it struggled with what seemed like straightforward questions and statements I made.

At issue right now is a new telecommunications system that’s being rolled out across the country. It started with the agency’s national phone number and is working its way out to the all field offices and card centers nationwide, and all their local phone numbers. Central to it is an automated system that incorporates unspecified AI “enhancements.” 

Whether those enhancements will make things better over the long haul remains to be seen. Below, I’ll go over the details of what’s happening, my experience contacting the SSA and provide a few tips to navigate the new phone bot if you have to call in.

For more, don’t miss the four ways you could potentially lose your Social Security benefits.

Social Security’s ‘maddening’ AI phone bot

Earlier this month, The Washington Post reported on issues plaguing the Social Security Administration, and tucked in the middle of the article were some troubling details about the phone system. 

The article cited a frustrating experience for Jennifer Burdick, an attorney who represents people with or applying for Social Security Disability Insurance. Burdick noted, “many times when you say ‘agent’ it won’t put you through to the hold line, it’ll act like it didn’t hear what you said.” 

One of the Post’s reporters tried it out for herself, only to have a similarly frustrating and dizzying experience. She presented the bot with an issue that would more than likely need to be handled by an agent: not receiving a Social Security check in April. 

The reporter explained the matter to the phone bot simply and succinctly, only to receive an automated reply with information about the 2025 COLA increase, Medicare Part B information, and other benefits available to recipients — none of which were relevant or helpful. Only after eight attempts did the system respond correctly and begin transferring the call to a person. 

MSNBC last week picked up the story and shared a video of the reporter’s “maddening” experience. (While that video refers to the tech as a chatbot, it’s really more of a classic phone bot, apparently with some AI elements but different from AI chatbots like ChatGPT and Gemini.) 

Read More: Social Security Check Missing? Here’s What to Do

I tried calling the SSA to test the AI bot’s skills

Spurred by those accounts, I wanted to see for myself how the phone system was working. I called in not once, but 11 different times. Mostly my experience was much more positive, but when the phone bot went wrong, it went very wrong.

When I asked, “Why is my payment lower than I thought it would be for this month?” the bot completely missed my point. It replied with the maximum benefit amounts for 2025 and how payments differ by age. I tried to clarify: “I’m already receiving benefits, and only this check is lower than it typically is” — to which it replied that the SSA checks its records between October and March to determine if an account needs an adjustment.

I repeated my initial question and received the strangest answer yet: “OK, direct deposit. If you’re finished, feel free to hang up. Otherwise, how can I help you today?”

Yeah, that’s pretty maddening.

Other times, it would take a long-winded route that did eventually lead me where I wanted to go. When I said, “I didn’t receive my payment last month,” the bot provided the full payment schedule for the month of May in detail but followed with, “To report a missing payment, just say ‘agent,'” and when I did, it correctly sent me over to the next step.

My takeaway: Maybe AI is working somewhere behind the scenes, but you can’t trust it to understand natural language — the way people speak in normal conversation — which is something that AI chatbots like Gemini Live are getting really good at, which I know from experience.

The trick, I discovered, was to forget about speaking to the phone bot conversationally. Instead, I hammered home on a single word: “agent.” On five separate calls, when all I did was to say “agent” whenever prompted, I got past the phone bot and into the queue to wait for an actual human agent. (Given the long wait times typical of calling the SSA, I didn’t stick around after that point.)

So yay! Success after all.

My tips for making the phone bot work for you

Here’s what I’d suggest when trying to deal with Social Security’s new phone system. 

Prioritize getting to a person, not the problem

The Social Security phone bot clearly has some issues to work through. Phone systems like this are notoriously bad — think of those times you’ve called customer service for, well, just about any big business — so you shouldn’t assume it’s going to be as understanding as when you’re speaking to a more sophisticated AI bot like Gemini Live. 

When the bot asks you what you need help with, just continue to say you want to speak to an agent. 

Keep words to a minimum

I think the success I had with the phone system could have been because I kept my responses to “agent” every time I was prompted to speak. Overexplaining to an ill-equipped AI bot likely won’t yield the results you want. 

Don’t call using speakerphone

If the phone system already performs poorly, don’t make it worse by introducing extra noise that can further degrade the experience, like when you call on speaker phone. Stick to using headphones that have good call quality or just have the phone to your ear and speak directly into the microphone when making your requests. 

Your mileage still may vary

Even these tips may not prevent a poor call system from interpreting your request correctly. If it begins to send you in circles, hang up and call back to see if that can get you where you need to go faster. 

A spokesperson for the SSA told the Washington Post that the phone bot feature is constantly improving and several factors can affect the quality of the call, including background noise, call connection and speech clarity. None of these things seemed to be an issue on the Washington Post reporter’s phone call. But my experience wasn’t as awful as that, so maybe the system is getting better, at least a little. 

For more, don’t miss what the experts are predicting for the 2026 COLA increase.

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