Email sent successfully but not being being received by emails using 365?

[David Smith]

Hi there,

So the logs are stating the emails are all sent ok and I am receiving emails ok to mail providers such as Gmail, Yahoo etc…

However, no email are coming through to customers’ emails that are using office 365. I have tried two different 365 mailbox accounts, but the emails just don not arrive?

Diagnostic output if this help? Thanks in advance for any help to ensure this works for customers using 365 emails

Mailer: postsmtp
HostName: jitterbyte.com
cURL Version: 7.58.0
OpenSSL Version: OpenSSL/1.1.1
OS: Linux quizzical-fermi 4.15.0-122-generic #124-Ubuntu SMP Thu Oct 15 13:03:05 UTC 2020 x86_64
PHP: Linux 7.3.27 en_US.UTF-8
PHP Dependencies: iconv=Yes, spl_autoload=Yes, openssl=Yes, sockets=Yes, allow_url_fopen=Yes, mcrypt=No, zlib_encode=Yes
WordPress: 5.6.1 en_GB UTF-8
WordPress Theme: TheFox
WordPress Plugins: All in One SEO, Code Snippets, Contact Form 7, Google Analytics for WordPress by MonsterInsights, iframe, WPBakery Page Builder, Client Portal by Laura Elizabeth, Login Logo, Popup Maker, Office 365 for Post SMTP Extension, Post SMTP, Slider Revolution, WP Table Builder, ReCaptcha v2 for Contact Form 7
WordPress wp_mail Owner: /var/www/vhosts/senditsecure.net/jitterbyte.com/wp-content/plugins/post-smtp/Postman/PostmanWpMailBinder.php
WordPress wp_mail Filter(s): wp_staticize_emoji_for_email, PostsmtpMailer->get_mail_args
WordPress phpmailer_init Action(s): wpcf7_phpmailer_init
Postman: 2.0.21
Postman Sender Domain (Envelope|Message): jitterbyte.com | jitterbyte.com
Postman Prevent Message Sender Override (Email|Name): Yes | Yes
Postman Active Transport: Office365 API (https://amazonses.com:443)
Postman Active Transport Status (Ready|Connected): Yes | Yes
Postman Deliveries (Success|Fail): 50 | 0

[Tim]

Hi David,

That’s unusual. Are you sending from @jitterbyte.com? Normally this would sound like an SPF issue, but I checked yours and it’s set up completely correctly.

Does the issue affect mail sent only to your internal Office 365 accounts, or all Office 365 accounts, including ones not in your tenancy.

Thanks.

Kind Regards,
Tim

[David Smith]

Hey Tim,

Thanks for quick reply.

yes, we are sending from an actual 365 mailbox…partners@jitterbyte.com

We did check the SPF records. It appears to affect all Office 365 account. I have only checked two though; one in and one out of our tenancy – as have no other 365 email to check against.

Issue seems to be pointing at 365 emails for some reason?

Thanks,
David

[David Smith]

Update: I’ve checked the quarantine and it is being blocked because it doesn’t have a PTR Record?

view the screenshot here: https://ibb.co/Jx05kzq

[Tim]

Hi David,

Thanks for the reply. Does the console give any indication what doesn’t have a PTR record? I checked the IP for jitterbyte.com and it has a perfectly valid PTR record set. I’d be surprised if any Microsoft IPs were misconfigured too!

Kind Regards,
Tim

[David Smith]

I can’t see to post here this morning..Having trouble replying!

[David Smith]

OK..so I have looked into the email logs and noticed the Delivery URL’s are different with different processes. One of which gets sent fine and and the other gets blocked.

Both of these processes generate a WP email response.

LOST PASSWORD RESET LINK..(DOES NOT ARRIVE AND GETS BLOCKED)
This is a standard WP generated email when users clicks the lost password link.
Delivery URL: smtp:none:none://localhost:25

ADD CLIENT TO PORTAL..(ARRIVES SUCCESSFULLY)
This is a WP plugin but generates a WP email when I assign users to a portal. This sends find to all emails, including Outlook.
Delivery URL: https://amazonses.com:443

Does the Outlook 365 plugin not change the delivery URL for all of the email sent from WP..as the smtp localhost:25 appears to be throwing up issues with Outlook emails.

[David Smith]

Hi Tim,

I was wondering whether you could should any light on the different ‘Delivery URLS’? the smtp:none:none://localhost:25 is being blocked and quarantined but the amazonses.com:443 sends fine.

Why are they sending from different delivery URLs and how can I change the localhost? Does the plugin affect the send URL’s at all?

Thanks in advance

[Tim]

Hi David,

Sorry I am only just replying. It has been a while since we last spoke, so just to confirm are you having issues with WooCommerce emails – or was it something else sending mail over the Office 365 API. There is unfortunately a bug in the extension that is sending the mail from localhost, and that’s probably why they are being quarantined.

Unfortunately, as the developer is very busy, I don’t have an estimate fix time as yet. Sorry about that. 🙁

Kind Regards,
Tim

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