On 2020-12-18 at 15:58 +0100, Jaroslaw Rafa via mailop wrote:
> > SendGrid. They have a webpage that says "We continue to retry
> > messages for up to 72 hours," but they (sometimes?) don't.
> 
> They do for most customers, but for some they don't.
> 
> I remember this issue with password change confirmations on Spotify,
> they were using Sendgrid at that time (don't know if still are?)

Is it a "please input this code to confirm you are the one changing
your password"? That actually makes sense. If the content of the
message is no longer needed before it gets delivered, you could skip it
(why would you queue for a week an OTP which was valid just for 5
minutes?). There is a RFC with a smtp extension for that, even. I guess
Sendgrid api may have as well a parameter to set the maximum time to
attempt delivery.

So there are a few messages which are low-value themselves and where it
is not needed to queue for a long time. For the most part, they SHOULD
be retried, though. It's not even hard to do. If you have a “dumb”
client which is not able to queue and retry itself, simply point it to
an internal MTA (assumed to be always up) and let that one take care of
communicating with the world.
Quoting rfc 5321: “the give-up time generally needs to be at least 4-5
days”

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