How I wasted time with an unhelpful Alaska agent – and what I’d do differently next time

These days, customer service is often underwhelming (and that’s true nearly across the board). One thing I generally appreciate is that many travel loyalty programs have invested in chat support, whether via their own app/website, text message, or WhatsApp. Generally speaking, I highly prefer customer service via one of these chat methods to calling, because I don’t need to sit around waiting with the phone to my ear, I don’t need to worry about whether I can hear the agent clearly, I can handle things “in the background” while multi-tasking, and I have everything in writing (which eliminates a lot of potential for mistakes). However, one downside of chat-based support is that it sometimes feels like it puts agents under pressure to resolve inquiries quickly, which doesn’t always lead to the best customer service. An interaction I had yesterday reminded me of my old advice: when you get an unhelpful agent, move on as quickly as possible.

I cancelled an award, but didn’t get the miles back

The reason I was chatting with customer service is that I canceled an award ticket a few days ago, and while the taxes were refunded as expected, the miles had not been redeposited into my account. The redeposit should have been more or less instant, so after several days, I figured something must have gone wrong.

I had originally booked four of us to fly from Boston to Bangkok via Frankfurt, Germany, on Condor Airlines, with a week-long stopover in Frankfurt. I made that booking about 10 months ago. Plans have since changed, and we aren’t taking that trip, so I canceled our reservation several days ago. About 36 hours after canceling, I received emails from Alaska customer service indicating that the refunds for the taxes had been processed and that I would see them on my credit card statement in a few days.

Sure enough, three days after canceling, the refunds showed up on my credit card statement. That was the good news. Unfortunately, although the cancellation page indicated that I would receive a refund of 340,000 miles for the four passengers on my itinerary, the miles were never refunded. That’s not typical of my experience with Alaska.  I’m not sure why that process got tripped up here, but I wanted to reach out and get that resolved.

Alaska offers customer service via chat

The Alaska Airlines app offers a help section. While logged in to my Alaska account, I clicked on the ability to chat with customer service. As an Alaska Atmos Silver member, I probably qualify for some expedited phone service, but I figured this would be easier to deal with “in the background” via text message.

In fairness, the text-based customer service is to chat with “reservations”. Alaska Atmos has a phone number. I figured this could probably be handled via chat instead of needing to call.

I started the conversation by explaining the issue, and I instantly got a response saying my expected wait time would be 25 minutes. That was fine.

I went on to share the confirmation code and the number of miles that I expected to have redeposited from the cancellation.

About 25 minutes later, I received a response from a customer service agent who asked how she could help. I copied and pasted the messages I had already sent. She replied, saying, “I’m sorry the points were not returned yet. One moment, please, while I transfer you to an agent in Atmos Rewards for further assistance”. I said “thanks” and prepared to wait “on hold” again. Getting transferred to an Atmos Rewards agent sounded like a good sign!

I’m including timestamps with these next three messages I received so you can see how quickly they happened.

At 5:48 p.m., I got a message saying it would be a wait of 29 minutes to speak with an Atmos agent. One minute later, an agent responded, saying to give them a moment to read through the conversation with the last agent. That was great news as it meant no wait at all! But then the agent immediately sent through a second message, asking if I was still there and warning that they would end the chat shortly due to no response. What? They just asked for a minute to read the previous messages!

Those messages literally came in back-to-back, so while it looks like there was a minute between when the agent introduced themself and when they told me they would have to end the chat for no response, I assure you those two messages popped up at the same time on my side.

I immediately confirmed that I needed help and thought they needed a minute to read the previous messages. They responded again, asking what I needed help with — immediately following once again with the warning that the chat would soon be ended for no response.

At that point, I became a little annoyed. I don’t mind waiting 20 or 30 minutes for an agent, but then rushing to cut off the chat without even reading the previous comments about my issue just didn’t make sense.

However, I imagine that agents are under pressure to resolve each customer inquiry quickly. The fastest way to resolve the chat is probably to say you ended it due to no response. It’s kind of like a McDonald’s that marks an order as “completed” long before you’ve been served to keep their speed metrics up. I get it — there’s probably a little gaming going on, and I try not to hate the player.

I replied by copying and pasting my previous messages to explain the fact that my miles hadn’t been redeposited.

The agent then replied, asking for passenger information for the booking. I provided my name, email, Atmos number, and all of the passenger names and birthdays, as requested. After 10 minutes with no response, I asked if there was any further information they needed from me. The agent finally replied that I needed to call for assistance and provided the phone number.

I was confused, since the first agent said she was transferring me to the Atmos team, and this agent had asked me to confirm everyone’s personal information. If the agent couldn’t help, I wondered why they had just asked for all of our personal information?

When I asked for clarification, the agent went on to say that they checked my account and were referring me to call because they were unable to see any points used for this reference number. I immediately went to my account history so I could reply with the date the points were taken, but in the ~90 seconds it took me to go back through that history, the agent immediately asked if there was anything else they could assist with, one minute later responding to say that they would end the chat due to no response. Again, these messages are each time stamped one minute apart, but there couldn’t have been two full minutes between them.

Before I could reply with the transaction date that they could have found if they had scrolled back in my account history or asked me when I booked, they had cut off the chat. I literally replied seconds after they ended the chat (timestamped with the same minute), saying that I still needed help….which sent me back to the beginning of the process.

I was frustrated. An hour had passed since I started the chat, and I was back to square one. Again, I understand that the core issue here is probably not this agent’s fault. Agents are probably pushed to “resolve” as many inquiries as possible in as short an amount of time as possible, and marking a conversation completed due to no response probably counts the same as actually resolving it. I don’t really hold that against them. That’s a systems issue. Still, I was annoyed that I waited 10 minutes for a response in the middle of the conversation, but this agent neither asked me for more information nor gave me 3 minutes to reply. If we were on a voice call, that would seem reasonable enough (if I hadn’t responded in 3 minutes via voice, I could see hanging up on me). But one of the core reasons to choose text-based service is the desire not to be tied to the phone for an hour, waiting to jump in and respond.

At this point, if I didn’t write about this stuff, I’d have just called customer service. However, I was curious to take another swing at text-based service to see what would happen.

The second time was the charm (thanks to Rob in Boise!)

More than half an hour later, a new agent responded. This time, the agent kicked things off by saying, “Hi, this is Rob in Boise with Alaska Reservations. How may I assist?”. I immediately felt confident that this interaction would be different.

I have always heard from Alaska loyalists that if I needed help with an Alaska issue, I should call the customer service number as many times as necessary until I got someone in Boise, Idaho on the line. I’ve always been told that the Boise agents are excellent.

I recapped the issue for Rob, explaining the cancellation, tax refund, but lack of redeposit (and the fact that the previous agent told me I needed to call because he couldn’t see the miles taken from my account, but I could tell them the date the miles had been taken). Rob asked for the confirmation code and my Alaska Atmos number — but then immediately said he could see it from the previous chat. Rob even apologized for asking for information he could see from the previous chat history. Talk about an immediate difference!

Rob went on to tell me he had to check with another desk — and 12 minutes later, he told me to refresh, and I’d see the miles.

Start to finish, once Rob picked up the chat, it was resolved in about 20 minutes — without pushing me to respond under threat of ending the chat (though, truth be told, I made sure not to leave time for that!). I told Rob he was an all-star and asked how I could nominate him for employee of the month. He thanked me and ended the chat.

My takeaway: I should have just tried again when the first agent rushed to end the chat

I share this story not because the relatively poor service from the first agent is a huge deal. It isn’t.

Instead, I share this for two reasons.

The first is to point out that I handled the first agent incorrectly. The moment that the agent tried to end the chat without even reading my comments, I should have realized that it was time to move on. I have often said that you can’t make someone help you and that there’s no sense in wasting time with an agent who doesn’t want to help — instead, just try again with another agent. I failed to follow my own advice here. My issue would have been resolved much faster if I had let that first agent end the chat either the first or second time they tried — it was only going to be a matter of time before they successfully “got” me, and I should have seen that coming instead of trying to push ahead. And if I had just gotten myself to a “Rob in Boise” faster, I’d have been less frustrated and not sitting at the dinner table with my phone in hand waiting for a response. That part is on me.

However, I also bring this up to point out the differences in how chat-based support is handled across different programs. In most of my past experience with airline and hotel customer service via text / WhatsApp / Twitter / Facebook Messenger, gaps in the conversation have been fine. I tend to prefer text-based support specifically so that I’m not focused on the call/chat. With Hyatt, I have frequently had a conversation continue across more than one “X” (Twitter) agent over the space of a couple of hours (the same with T-Mobile). My WhatsApp interactions with JetBlue have been faster, but without pressure to respond quickly. I’ve used chat support within the United Airlines app and been able to leave the app and come back to continue the conversation. Most text-based support has become as good or better than calling.

That said, some programs clearly lag behind. I tried chatting with Avianca yesterday via WhatsApp, but their WhatsApp support is only an AI chatbot, so it isn’t very useful. I had a similar experience with Iberia last year and was ultimately unable to reach a live agent. I think that sort of thing is a huge miss for programs these days. For all the reasons I stated at the outset, I prefer text-based customer service. And from a program standpoint, a single good agent can probably handle multiple chats at once. And, as AI continues to improve, there will probably be an increasing number of tasks that an AI bot can handle.

In the meantime, the quality of chat agents certainly can vary. If you get an agent who seems rushed or unable to help, save yourself some time and move on to a new agent. Rather than get frustrated, get yourself connected to Rob in Boise sooner rather than later.

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