In-flight Wi-Fi vs. your eSIM

They're unrelated. Your plan connects to networks on the ground, which can't be reached at cruising height, so it doesn't work mid-flight whichever plan you have. In-flight Wi-Fi, if the airline offers it, runs over satellite. It's a separate service you buy from the airline.

More detail

The useful overlap is on the ground. If you added your plan before flying, leave data roaming off for the KnowRoaming line until you land. Nothing starts until it connects. Once you've landed and the phone is out of Airplane Mode, turn roaming on for the KnowRoaming line and give it a minute. Your plan begins; the taps are in your platform guide.

On the airline's Wi-Fi anyway? That's a fine moment to buy or add a plan for where you're heading, so it's ready when the wheels are down. See Buying while already abroad. Your plan starts when you connect in a supported country, not when you buy. Your validity days count from that first connection. Unused data expires at the end of your validity period. It doesn't roll over.

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