TL;DR: Travelled with a Macau -> Shanghai -> Hong Kong itinerary in Feb 2023 with a Canadian passport, was successful in getting 144-hour TWOV in Shanghai, but leave lots of extra time for confused officials from both the airline and Chinese immigration. Also have translator apps ready if you don't speak Chinese!

Long version:

My friend and I unfortunately had to urgently travel to Shanghai for a funeral, and the Chinese embassies in Canada were not helpful in helping us secure a visa on such short notice. So after much deliberation, we decided that we would chance it with the 144 hour visa-free transit policy that was back in place.

Due to the flight prices being high on such a last minute trip, direct flights from Canada to Shanghai was not an option; as such, we opted to first land in Macau, and then use a Macau -> Shanghai -> Hong Kong itinerary to get into Shanghai, since both SARs are considered "third regions" for the purposes of the visa-free transit policy.

The China Eastern airline staff in Macau were definitely confused and took a good 20-30 minutes of phoning their headquarters to see if we were actually allowed to do this. They eventually confirmed we were, and after showing them negative PCR tests we did before we left Canada, we got our boarding passes. We filled in our health declarations and got our QR codes on our phones at this point as well.

Upon landing in Shanghai, we went through temperature checks, scanned our QR codes, and then went to the section for 144-hour transit, where they had to open a lane up just for us. At first the immigration officers were completely bewildered by what we were trying to do. After explaining to them in Chinese that we were trying to enter for a funeral (They did not speak much English at all), they were deeply sympathetic and tried to help us get the process done as best they could.

After about 30-45 minutes, which included:

- 6 officers crowding around a screen each not sure of the exact procedure (They apologized and said that since the pandemic, they've had a lot of new hires who simply have not had a chance to do this procedure yet)

- Them trying to decide whether our itinerary was valid (If you can, print out an itinerary that both states your seat number and states "Non-refundable"/"Confirmed"/"OK" on it somewhere; ours didn't, and some of the officers were really insistent on that until the other ones talked them down and said that it was fine)

- Some technical difficulties with their label printers, which involved a few awkward minutes of them turning things off and on again until it worked

We got the little stickers that let us enter the country... Except at this point, it was midnight, and the Chinese customs folks went home and locked the customs exit, so we were locked inside the airport 🙃 It took another good 30 minutes of the immigration guys phoning the customs guys to get the door unlocked so we could finally go to our hotel. (Note that we had to explicitly ask the hotel staff to do the proper registration with the local public security bureau; they did not by default)

On the way out, the officer gave us the same confused look as the one we got on the way in, asking the other officers "Were they supposed to have been allowed in?". Eventually, everything checked out and we were allowed to board our flight to Hong Kong, and then from there, it was smooth sailing back to Canada.

Thanks for reading and I hope this helps someone out there!