Texting Delta no longer gets you a real person. Those messages now trigger an auto-reply sending you to Delta Concierge, the AI assistant in Delta’s app. It can track a bag or find a travel credit just fine, but when a canceled connection leaves you stranded, you want an agent who can find options the app won’t show you. The humans haven’t gone anywhere. They’re just harder to reach, so here’s how to get through to one faster. Fittingly, a top-tier Delta elite who recently complained about the airline’s chat support got an email reply that still opened with the AI prompt asking for a warm, empathetic tone. Someone forgot to hit delete.

Then there’s travel insurance, which most of us decline at checkout without a second thought. For a cheap weekend with refundable plans, your travel credit card’s coverage may be plenty. A separate policy can matter more if you get sick or hurt abroad, or for a honeymoon or group villa you put on your card while you’re still chasing everyone on Venmo.

And if you’re driving to the airport for Thanksgiving, consider reserving parking now. Busy airport garages can fill up, even on a normal travel day.

👉 Read our full travel insurance guide

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If your flight gets cancelled, ask whether the airline can rebook you on a partner airline. It’s often possible even if the agent doesn’t offer it first.

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There used to be an easy way to text a real person at Delta instead of sitting through hold music. Well, not anymore, and I have some thoughts.

This is Departure Digest, and happy Halloween. Let’s talk about how to still get a human at Delta, why you might need to book airport parking ahead of time, and when travel insurance actually makes sense.

So, here’s what happened.

For years, you could tap Message Us in the Fly Delta app, and it would pull up a regular text on your phone. Then you could go about your day until an agent texted you back.

But now, if you text that number, you get an auto-reply pointing you to Delta Concierge, the AI assistant in the app.

The AI concierge itself isn’t new. It’s been open to all Delta SkyMiles members since August. What’s new is that it’s now where you end up when you try to message Delta. It can cancel a trip, track your bag, rebook you after a delay, and find any travel credit from a canceled flight.

Delta didn’t get rid of humans, at least not yet. You can still call, or ask Concierge for a real person. But it can take a lot longer to reach someone than it did over text.

And look, we love AI around here. For something quick, I’d much rather tap a few buttons than talk to anyone. But the complicated stuff is different. Say your connecting flight gets canceled, and the last flight home is about to take off. A good agent can find options the app won’t show you, like a seat on another airline, or they might bend a rule for you.

And when everything’s falling apart, finding a human shouldn’t feel like a maze.

So when that happens, ask for a person right away. Concierge will try to fix it on its own first, so you might have to ask more than once.

If you have elite status with Delta, skip the main number and call the Medallion line in your app. And if you have lounge access, the agents in the Delta Sky Club can rebook you too.

If a snowstorm cancels everything, do all of it at once. Open the chat, call, and get in line. Whoever gets to you first wins.

Also, for a lot of airlines and hotels, sliding into their DMs on social media can be one of the fastest ways to get a real person.

Okay, at least Delta gives you a few backup plans. My friend’s airport garage did not.

I don’t have a car, so airport parking has never really been on my radar. But a friend recently drove to the airport, and the garage was totally full. Not exactly ideal when you’ve got a flight to catch.

A lot of airports let you reserve a spot online ahead of time, kind of like a dinner reservation. At busier airports, parking can sell out, even on a pretty normal travel day. And depending on the airport, booking ahead can be cheaper than paying when you show up.

The move is to book parking when you book your flight. If you’re driving for Thanksgiving, I’d do it now. Check the cancellation policy first, though, since some of them don’t give refunds.

Parking is the low-stakes version of planning for things to go wrong. Travel insurance is the high-stakes version.

Most of us click no on the travel insurance box at checkout without thinking twice. To me, it’s there to protect the money you won’t get back, like a hotel you can’t cancel or a tour you already paid for.

A lot of travel credit cards already come with some coverage, like if your trip gets canceled or delayed, or your bag gets lost. The catch is you usually have to pay for the trip with that card, and it only covers certain situations.

A separate policy can help most if you get sick or hurt abroad. Your regular health insurance may not cover much outside the country, and if you ever need to be flown somewhere for care, that bill can be huge.

For a cheap weekend where most things are refundable, your card is probably enough. But for a honeymoon, a big international trip, or a group trip where you put the whole villa on your card and you’re still chasing everyone on Venmo, having both can make sense.

If you want what’s called cancel for any reason coverage, which gets you part of your money back even if you change your mind, don’t wait. You often have to buy it within a couple of weeks of putting down your first deposit. I’ll link our full travel insurance guide below.

Alright, that’s all I’ve got this week. And just a quick reminder, the clocks fall back an hour Saturday night, so if you’re out late for Halloween, you get an extra hour of sleep.

Have a fun weekend, and I’ll see you bright and early Monday.