WireMailGmail : Emails not always arriving?

[reed]

Hey y'all — 

I've got a weird issue. I set up the WireMailGmail module to send emails for the LoginRegister module, and it's been working great. All my tests have sent instantly, and users from around the world have successfully logged in. 

Here's the problem: I work with a school, and they're not receiving the automated emails from my gmail account. They do get emails if I send them manually from the same gmail account. Any ideas what might be causing this issue?

Thanks a bunch for any thoughts —

Reed

[eydun]

Is the school perhaps using Microsoft Office365? Then it is possible that the emails get blocked by Microsoft's spam-filter.

 

[reed]

Oh snap — maybe? I've reached out to the school's IT group, and there's a whitelist they're gonna put me on. We'll see if that helps. I'll find out if they're on MS Office365, and report back ?

[dragan]

On 8/26/2019 at 4:20 PM, reed said:

Here's the problem: I work with a school, and they're not receiving the automated emails from my gmail account. They do get emails if I send them manually from the same gmail account. Any ideas what might be causing this issue?

Not even in their spam folder? Try to send an automated email to yourself, then compare the mail headers (manual vs. automated). Perhaps you'll spot a difference there (maybe automated mails are lacking SPF records).

[reed]

It looks like @eydun called it — the school uses MS Office365, which was quarantining my emails. I got on their whitelist, and now my emails are going through just fine. However, it is gonna be a consistent problem, since some other schools are reporting issues as well ? 

And @dragan — I think you're right — I looked at the headers of automated emails vs manually sent emails, and there are differences. I'm not totally sure what I'm looking at, but I'll share the code tomorrow, and maybe there's something conspicuous to a more practiced eye than mine ? 

[teppo]

Just for the record: SPF records are specific to domains, so that's not something you'll find in the messages specifically. If you're using a domain that has SPF record in place, your best bet would be making sure that wherever Gmail is sending the messages is included in that record – though if those "manual" messages you mentioned were sent with same host/domain and also via Gmail, that's probably not the issue.

When you say that there are differences in the headers, I'm wondering if you're sending manual messages directly via the Gmail UI, and automated messages via code, or something along those lines? Definitely make sure that you're using correct (and identical) domains etc. For a better idea about what might be going wrong, be sure to give one of those testing services (such as https://www.mail-tester.com/) a try, i.e. send an identical message to them and see if they flag any issues.

And finally, keep in mind that automated messages often look suspicious based on their content alone – short text with various flaggable keywords and a link (or worse yet, multiple links). I've had plenty of trouble in the past getting such messages through reliably, particularly if the receiver has strict anti-spam filters in place. Assuming that those messages are customisable, you might want to try rewrite them to look more "natural" ?

[eydun]

8 hours ago, reed said:

It looks like @eydun called it — the school uses MS Office365, which was quarantining my emails. I got on their whitelist, and now my emails are going through just fine. However, it is gonna be a consistent problem, since some other schools are reporting issues as well ?

I has been my experience that Microsoft's mail-servers, such as Office365 and Hotmail, are the most aggressive to filter out incoming e-mails that are suspected to be spam. Often they even do not make it to the spam-folder in the user's mailbox.