Mail has never worked very well in GAE.
- Sending messages will sometimes fail for no reason, so you have to put the code to send any important messages into a task so it can retry
(Note that since URLFetch also fails for no reason, with alarming regularity, I suspect sending email via SendGrid will need the same protections)
- The headers GAE put into the message are awful, and scary, and convince users that they are looking at spam. For example, gmail shows this one:
- Despite DKIM, SPF and friends, a lot of GAE-sourced email gets blocked by corporate spam filters
- Quotas are really tight when first getting started, and never get all that loose
- The "from" address of any email you send MUST be either an admin or a user logged in via google oauth
- Google's #1 priority with outbound email is that GAE not become a spam platform, and this colors every technical decision they make around email
And yes, if you rely on GAE for bulk email, you are definitely getting yourself into trouble.