Let us know if the “so messages are always executed on the same request” works. Otherwise, you might want to sign up with a transactional email service, such as Mailgun or SendGrid
So switching to send on the same request allowed the emails to send?
If so the issue is most likely with WP Cron rather than Sendgrid.
If you go to Tools -> Site Health and wait about 30 seconds for the tests to complete does it show any errors about scheduled events or loop back requests?
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