Time to get that paid account to good use and contact Google support for them to do something. 

freitasm:

Time to get that paid account to good use and contact Google support for them to do something. 

turtleattacks:

 

Thanks - looks like our outgoing email IP is on a blacklist. https://mxtoolbox.com/SuperTool.aspx?action=blacklist%3a209.85.218.54&run=emailheaders 

 

Where did you get this IP address from?

turtleattacks:

freitasm:

 

Time to get that paid account to good use and contact Google support for them to do something. 

 

Been in touch with them this afternoon. They said that from their point of view, the email was successfully sent.

And that dynamic IP addresses cycle so it should be fixed in 24 hours. Funny that the wife told me about this issue earlier in the week.

Just to be clear for my thick head - it’s the Google mail IP address that’s black listed right?

Looking at the email you sent me the address is mail-ej1-f45.google.com (209.85.218.45). This is their server and has nothing to do with your "dynamic IP address".

Their server is blacklisted, they have to deal with it.

We have had this exact same issue with Gsuite/Workspace for the last couple of years and it mostly affects Microsoft hosted email recipients.

The problem is Gmails mail servers dynamic IPs get black listed by SORBS (because spammers use the same ones) and it takes them weeks to take any action and then it just happens all over again.

We were continually requesting SORBS delist the IPs and they would but it became too much of a headache and not worth the hassle so ended up moving to a static IP address through Amazon SES. No problem since!

You can send an email to ping@tools.mxtoolbox.com and it will reply and let you know if the mail server you used to send the email from is being blacklisted by anyone.

RexHavoc:

 

We have had this exact same issue with Gsuite/Workspace for the last couple of years and it mostly affects Microsoft hosted email recipients.

 

The problem is Gmails mail servers dynamic IPs get black listed by SORBS (because spammers use the same ones) and it takes them weeks to take any action and then it just happens all over again.

 

We were continually requesting SORBS delist the IPs and they would but it became too much of a headache and not worth the hassle so ended up moving to a static IP address through Amazon SES. No problem since!

 

You can send an email to ping@tools.mxtoolbox.com and it will reply and let you know if the mail server you used to send the email from is being blacklisted by anyone.

 

I assume that we can't use the Gmail interface on AWS SES? Most of our emails are stored there. 

turtleattacks:

 

I assume that we can't use the Gmail interface on AWS SES? Most of our emails are stored there. 

 

All incoming email comes to our Workspace account but we use MS Outlook to receive/read/send and manage our emails. The only change we made was using Amazon SES as our SMTP outgoing mail server.

see: https://docs.aws.amazon.com/ses/latest/DeveloperGuide/dedicated-ip.html

Obviously there is an extra cost depending on your needs.

Mind you, changing the SMTP outgoing server will require changes to SPF and DKIM DNS selectors (in addition to GWS in case someone still uses GWS for something or another).

RexHavoc:

turtleattacks:

I assume that we can't use the Gmail interface on AWS SES? Most of our emails are stored there. 

 

All incoming email comes to our Workspace account but we use MS Outlook to receive/read/send and manage our emails. The only change we made was using Amazon SES as our SMTP outgoing mail server.

see: https://docs.aws.amazon.com/ses/latest/DeveloperGuide/dedicated-ip.html

Obviously there is an extra cost depending on your needs.

 

 

RexHavoc:

 

We have had this exact same issue with Gsuite/Workspace for the last couple of years and it mostly affects Microsoft hosted email recipients.

 

The problem is Gmails mail servers dynamic IPs get black listed by SORBS (because spammers use the same ones) and it takes them weeks to take any action and then it just happens all over again.

 

We were continually requesting SORBS delist the IPs and they would but it became too much of a headache and not worth the hassle so ended up moving to a static IP address through Amazon SES. No problem since!

 

You can send an email to ping@tools.mxtoolbox.com and it will reply and let you know if the mail server you used to send the email from is being blacklisted by anyone.

 

Arg I am going to lose my mind. 

I understand, Whilst the above steps(SPF, DKIM and DMARC) help with issues with sending emails, I appreciate that you have stated that Google IP is listed on the 3rd Party database SORBS. Please note that issues with SORBS are outside the scope of our support offering and we won’t be able to offer you further direct assistance with SORBS at this time. However if you require additional support regarding SORBS, please contact them directly for assistance at http://www.sorbs.net/contact/supportreq.shtml

Apologies as we cannot change Google's IP address for your outbound emails. From what I've checked here on my end, your account should be good to go in terms of outbound emails. I can assure you that all the records needed for sending emails was correctly configured for your account. I'm really sorry for the inconvenience though about SORBS blocking Google's IP. If only I could do something here on my end, I'll gladly do so. But what I highly suggest now is to contact them instead for further troubleshooting.

Can someone please advise how much O365 is? We simply can not rely on a mail service where we can't be certain if an email has been received or not. 

turtleattacks:

Did you approach Google to address the issue or SORBS? Because Google support have no clue and from their end, everything was sent properly.

Yes, I contacted GSuite support at least 3-4 times (still have the message transcripts). They first checked SPF, DKIM and DMARC were correct and passed their own validation tests.
Each time they wiped their hands of the issue showing our emails had been delivered to the recipient. Their claim is technically correct, but the recipients mail servers seem to be setup in a way where if the senders IP address is on the SORBS blacklist they either delete the email outright or it gets marked as spam.
As I mentioned earlier, we had to request SORBS remove the IP from the blacklist each time. I was doing this 3-4 times a week via the SORBS website - http://www.sorbs.net/. Unfortunately due to the way Gsuite/Gmail rotate their IP addresses it became a never-ending task. These IP addresses appear to be used on all gmail accounts, even the free ones, so as soon as someone spams from a gmail IP address and SORBS detects it, it gets blacklisted. SORBS have a list of email addresses setup as Spam Traps. Here's one of their responses we quite often received from them...

"Any message sent to a spam trap is spam. The message that caused this listing is spam because it was sent to one or more of our spam traps. If you do not isolate the problem and stop sending messages to our spam traps the ip may not be delisted and if delisted will likely be listed again and again. The only way to stop getting listed is to stop sending messages to our spam traps. Please check your mailing lists for outdated or otherwise invalid email addresses and check for compromised accounts.

As we've seen no further spam occurrences, I've de-listed this IP. In order to assist you in identifying the source of the spam, I've attached the headers for the most recent occurrence. This may point to a compromised or unsecure mail account or mail server, or a computer infected with a spambot, among other possibilities."

The headers they provided were never sent from my company, just someone else using Gmail.

For us the only fix was moving to a dedicated IP address. One of our automated emails we frequently send to ourselves cc's to 'ping@tools.mxtoolbox.com' so we can quickly check if there's any problems with our outgoing email, and we have never once had an issue.

turtleattacks: ... Can someone please advise how much O365 is? We simply can not rely on a mail service where we can't be certain if an email has been received or not. 

You can find out more for yourself by visiting Microsoft 365

• From NZ $7.60 to NZ $30.20 per month per user for Office Business
• From NZ $12.10 to NZ $ 86.20 per month per user for Microsoft Enterprise

Technically the emails have been sent successfully but the Google email server delivering the 'email package' is regarded as SPAM, hence it really should be Google that takes responsibility. 

Thanks for this guys, because the emails we send are medically sensitive and time critical. We simply can not afford emails being blocked/regarded as SPAM. 

I'll make the arrangements of migrating our mail service to Microsoft O365 next week.