Dealing with unknowledgeable check-in staff

Stay polite and friendly and from a position of "you don’t want to deal with not being able to check me in any more than I don’t want to go away unchecked-in." I had a gate agent in Toronto who fundamentally misunderstood the wording of a letter permitting me to travel to Singapore.

The gate agent asked "why are you going to Singapore?" and it’s not a secret, but she’s not an immigration agent trained in determining whether reasons are essential. So I told her "we have an approval letter, it’s for an essential reason" and I gave her my son’s letter.
That starts

APPLICATION FOR ENTRY IN VIEW OF 2019 NOVEL CORONAVIRUS
[Son’s name], Please refer to your application for entry regarding the above matter. I am pleased to inform that you may seek entry to Singapore between 30 Oct 2020 and 03 Nov 2020. The Immigration Officer at the checkpoints will assess your eligibility for entry, provided that you fulfil the usual entry requirements where applicable."

Now, Singapore never says "Congratulations, you are going to be let in." This is permission to present ourselves to an immigration person IN SINGAPORE and say "I would now like to come in." It is our approval letter. But she is all "this is just your application." No, I tell her, the application was 20 pages long, this is the approval. She keeps leaving (with our passports) and coming back and typing and then leaving again. Eventually she comes back with someone else and it occurs to me to show her the PDF from our Arrival Card submission. This is like a landing card used to be, but there are health questions. It is completely unrelated to whether or not you have permission to enter. But it starts:

Dear [Son’s name],
You have successfully submitted your arrival information and health declaration to the Immigration & Checkpoints Authority on 30/10/2020 22:55 (Singapore Time).

This proves that we submitted a Covid-related form which was optional, I could have used an app on my phone or waited till we landed, but BECAUSE I DID, I had the magic piece of paper that says "successful" on it.

Several times she said to me "this is your approval. I needed this." And I didn’t argue with her because I wanted to get on the plane. And we did.

Looking back now some years later I think she came to realize that she was wrong about the "you may seek entry" not meaning we had permission, and needed a way to save face. She found it on the health form. Had we been argumentative and unpleasant, she might not have gone for it. And definitely bring as many different pieces of paper as you can find, printouts of rules, printouts of emails, receipts, whatever you have, in the hope that one of them might change their mind or give them an excuse to announce "this changes everything" and let you on.

1. Make sure you have done your homework and have some documents to back it up.
2. A really good one to check is the IATA travel center https://www.iatatravelcentre.com/passport-visa-health-travel-document-requirements.htm. Airlines rarely disagree with this.
3. Be prepared to escalate to a supervisor, or simply try a different agent. An agent that actually works for the airline is typically more knowledgeable than a random contractor that works for 4 different airlines on any given day.
4. Make sure you’re clear about what exactly the problem seems to be. We had one agent reject our Covid tests since he had today’s date mixed up in his head.
5. Make sure the agent understands what you are talking about and explain if needed. We asked one check in agent to check whether our Global Entry number was on the booking for a flight to the US. He had no idea what this was, so we explained the concept of a Known Traveler number to him. After he understood he could call a supervisor and ask.

This has happened to me twice and it is a very stressful situation. Gate agents check the computer for what the rules are. The output is not whether any particular passenger can board but it can be a fairly long text explaining all the rules. The decision on how to interpret the rules is up to the agent.

Last time, I was initially told that I could not board because I did not have a return ticket within the 3-month limit of the TWOV. I had a return ticket but several months later. In this case, the wording was a little convoluted and the agent judged it would be ambiguous and wanted interpret them conservatively. We insisted calmly with the agent which called a supervisor and continued the conversation over a full hour. They showed us the computer output and we read everything line by line discussing our interpretation of the rules. We were really worried, not just to miss the flight but because we had shipped things ahead of us to the destination country. They let us in on time after letting them take copies of our paperwork, itinerary and plan. The contention point was centered around a statement that said the country may refuse entry but that visa extensions could only be applied from within the destination country. This was the conundrum, we knew that we wanted to stay longer but we were told by the embassy that it was only possible to extend at the destination. Had we known this ahead of time, it would have probably helped to ask a letter stating this from the embassy.

Another time I had problems boarding was due to fast-changing covid rules and the agents had outdated info that we not propagated to the system. I know these had just changed, so I brought print-outs and showed it to the agent which showed it to the supervisor. Again, I explained calmly but confidently that these were the latest rules.

So, to answer the question on how to deal with unknowledgeable staff is to be knowledgeable yourself and bring as much documentation as possible to support your point-of-view. In the end of the first time, the supervising agent congratulated us on having done our homework well. If you can, get the documentation from an authority such as embassy, even if it is a screenshot or printout of the info on the embassy website (that is what I had for the time regarding covid rules).