If I travel with 2 different companies will the second company that I check in with know my previous departure point?

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The second company that you're flying with would not know unless the itinerary is booked together, however there might be a passport stamp that you should worry about if you're travelling through an embargoed country.

However, countries like Cuba don't stamp your passport, they will give you a card with a stamp that you need to provide upon exit of the country. If you're traveling though a country that won't allow entry based on a previous itinerary (like going to Saudi Arabia after visiting Israel), make sure the previous country gives you a visa card and doesn't stamp your passport. Happy travels!

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