Why is the generated POT file from WordPress.org not adding my plugin description to the POT file?

The makepot code being used on WordPress.org is a slightly older version that we have not updated yet, specifically with this fix:
https://core.trac.wordpress.org/ticket/25665

Basically, it’s only looking in stripe.php for your main plugin lines, not searching for and then finding stripe-checkout.php.

This was fixed in the developer tools 7 weeks ago:
https://core.trac.wordpress.org/changeset/27399

But the change has not propagated to everywhere yet.