...Do you guys have any suggestion on how to debug this and find the cause?

Hire a consultant to do a code review?? If you told us more about your enviroment, we might be able to suggest things to examine.

It loses its content when it goes to the checkout page.

Whenever it happens, it sends an email to us and redirects the user to the start page to redo her booking. So we know when it happens, but it definitely will annoy users.

When its sending an email to you, what kind diagnostic information does it include?

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