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Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

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Posted on by 33

Hi all, 

Issue:

When sending emails from our Marketing model-driven app, we're noticing emails are not getting delivered to any of GMail email addresses specifically - but are not experiencing this issue for other email domains. i.e. we've tested email sends and can see those emails successfully delivering to contacts which have hotmail, yahoo, outlook, etc domains).  This issue is consistently across all of Marketing (regardless of whether we're just performing individual ad-hoc test emails (using the 'Send Test email' button when in the edit screen of a given email template, or if it's a segment based customer journey send).

Description and background:

As of yesterday (18th April 2023) our Marketing MDA was successfully sending and delivering emails to GMAIL email addresses (I've a recurring email setup that sends to various test contacts, and I can see emails from our PROD environment landing in my test Gmail email address acount's inbox as normal.  However when running email tests today, we're not seeing anything reach the inbox (or spam folders even). 

I've confirmed: 

  • Our Marketing MDA app is showing as fully up to date (version 1.93.2021.0 , this is matching the Microsoft documentation as found here). 
  • Our domain record is fully authorised and 'confirmed' (as back in Nov 2021), no recent changes have been made to this.
  • Furthermore, we have confirmed the 'ownership key' and 'cname' records are present in our sending domain's published .TXT and .DKIM records also.
    • When we send test emails to other email domains (hotmail, yahoo, etc) we're seeing SPF, DKIM and DMARC all being marked as 'PASS' as expected).
    • We're not seeing our organisation's domain appearing on any email blacklists (checked on MxToolbox).

Seeking guidance on where I might be able to find SMTP logs of emails that I've sent from our Dynamics PROD environment

Requests:

  1. Can anyone provide any other areas where we can troubleshoot here?  e.g. we've send emails via different channels (e.g. as a once-off adhoc email via Activities timeline, sent via a 'send a test' email from the edit email template screen, sent via a normal segment/customer journey via outbound marketing). 
  2. Can someone help point me towards where we can find and review the SMTP logs that would show the bounceback info for these failed GMAIL email sends please? 
    1. Is this info only accessible to certain user roles, or can a more broader user audience also gain access here (e.g. read-only access to SMTP logs could be useful to troubleshoot this type of issue in future).
  3. Does Microsoft have a public facing status dashboard for email server heath? (asking as our domain isn't appearing on any publically available email blacklists (and am assuming Microsoft's email SMTP servers are not suffering poor email sending IP / domain reputation). 

Thanks,
Liam

  • Verified answer
    LiamS Profile Picture
    LiamS 33 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    Hey,

    Just posting here to advise that following some back and forth with Microsoft dynamics support, their engineering team eventually were able to confirm for me that there was indeed an issue with *some* of their EMEA outbound email SMTP ip pool getting rate limited by Gmail domain back on 19th April.  

    Once their systems picked up they were getting throttled by gmail servers, their auto backoff policy kicked in, which resulted in the dramatically reduced email deliverability over a c. 12 hour period during the day of the 19th - which preventing outright blacklisting of the dynamics ip pool at least.   Following that 12hr period, normal service resumed (which tallies with the experience we saw too).  

    I got a "we have taken steps to reduce the likelihood of this happening again." response regarding future steps to help prevent this from recurring in future, which is a little vague but at least we know what the issue was here at least. 

  • LiamS Profile Picture
    LiamS 33 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    Hey,

    Yep, same thing here - around 9.05pm BST I saw my test emails coming through to Gmail.  

    So, I guess the question now becomes was it a delay in them being processed in the backend somewhere on Dynamics side, or were they caught up somewhere after they left dynamics SMTP servers, but before they reached Gmail SMTP servers... I'm following up with Microsoft in the ticket I raised yesterday to see if they've anything they can shed a light on, will share here if anything useful is highlighted to me.

  • StigG Profile Picture
    StigG 15 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    Yesterday evening around 10pm (CET) the non-delivered e-mails suddenly started being delivered. This includes journey mails that were sent before, as well as test mails I sent manually during the afternoon. It seems all of the Gmail-mails were held up in a queue somewhere, but eventually got delivered. This morning I tried again sending a test mail to my personal Gmail-address, and it got delivered instantly.

  • LiamS Profile Picture
    LiamS 33 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    FYI, submitted a support ticket so will let you know if we've any joy

  • StigG Profile Picture
    StigG 15 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    Also EMEA based. Yesterday everything was still working fine. However today we saw 55% of our mails being sent but not delivered. Turns out all are gmail-addresses.

  • LiamS Profile Picture
    LiamS 33 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    Interesting, perhaps might be a wider email server/environment issue then on Microsoft's side then.  Might stick in an official ticket their support, presumably if enough raise it, they'll be quicker to help action and remedy the problem (assuming it is indeed an issue from their side).  

    Our dynamics environment/tenant is EMEA based, where is yours based if you don't mind sharing?  

  • StigG Profile Picture
    StigG 15 on at
    RE: Emails failing to deliver to GMAIL email domain (but sends successfully to other email domains (e.g. hotmail, outlook, yahoo all working)

    We are experiencing the same issue. None of our contacts with gmail-addresses get our e-mails since today. In the journeys it says they are all sent, but none are delivered to gmail.

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