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Question Emails sometimes not delivered even though Sendgrid says it was (unrelated to Plesk, read full topic)

Denis Gomes Franco

Regular Pleskian
Hey everyone,
Long story short..... I run a web design agency that also hosts customers websites and online stores we develop using Wordpress and Woocommerce. We use Sendgrid as a transactional email solution, and an SMTP plugin set up to use our own Sendgrid account.

Sometimes a customer that uses a @hotmail.com/@live.com/@outlook.com will make a purchase and not receive any emails from the store, at all - according to him/her.

Weird thing 1: Sendgrid logs show that the message was in fact received correctly by Hotmail's servers. No blocking occurred, at all.
Weird thing 2: This does not happen with everyone. I have tested using my personal @outlook.com address and it was fine.
Weird thing 3: Customer swears that the messages are not in the inbox, not in the spam folder, not in any other folder, and not in the focused/other inbox.
Weird thing 4: This is very, very rare. Happens to maybe 1 or 2 out of every 100 customers - well, at least according to those that reached us saying that they had a problem.

The SMTP plugin is set up to send notifications using the store's email address, which most of the time is an address outside the domain (eg. joesbarbershop@gmail.com instead of sales@joesbarbershop.com). This is unavoidable and most owners don't want to switch, however I don't think this is the cause of the problem - as mentioned in #2 this does not happen with everyone, not with every @hotmail.com/@live.com/@outlook.com address.

I'm aware that this might not have any explanation or solution at all but... have someone seen something like this before? Maybe we missed something, a configuration somewhere?
 
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