Gmail Sent Through Outlook Client Goes to Spam

[MatthewMoran]

My client has a Google Workspaces domain. Some of their users send mail via Gmail online. Others use the Outlook application (NOT OUTLOOK.COM). 

Recently, any messages sent from the Outlook Application go to the recipient's spam/junk folder.

We are using the gmail smtp settings in Outlook. It is the latest version of Outlook 365. This happens whether this is Outlook for PC or for Mac. 

IMPORTANT: If we send the same message from gmail (mail.google.com) instead of from the Outlook application/client, the message is NOT marked spam.

This seems to be something that Outlook adds to the headers of the message. To date, we've unable to find a fix. Getting rid of Outlook for some users isn't really an option.

Any assistance would be greatly appreciated.

[#2]

Remove yourself from the blocked senders list - Office 365 | Microsoft Docs
In this article, you'll learn how to use the delist portal to remove yourself from the Microsoft 365 blocked senders list.


https://docs.microsoft.com/pl-pl/microsoft-365/security/office-365-security/use-the-delist-portal-to...
Hello is one link that helps when Outlook means as spam? But I'm looking for an even better answer!

[#3]

https://docs.microsoft.com/pl-pl/microsoft-365/security/office-365-security/outbound-spam-controls?v...
https://docs.microsoft.com/pl-pl/microsoft-365/security/office-365-security/use-dkim-to-validate-out...
I hope it will be helpful - please write if it worked?

[#4]

Hello @MatthewMoran,
I'll try to reproduce the issue. When you say "Outlook application" you mean Outlook for Windows? If so, what's exact version?
Also what happens if your client will run native Windows e-mail client instead of Outlook?

[#5]

@MatthewMoran Hi Matthew 

Did you find a solution for your problem as one of my clients is having exactly the same issue.

They are estate agents and need to use the Outlook software in conjunction with their managemnt software

When they send to any microsoft email address, eg outlook.com live or hotmail via Outlook it goes to the customers spam, but when they send via gmail web it goes tot he clients inbox

[#6]

@markmcbride1000 My friend has started running into this. It appears to happen when he uses Outlook AND when he is on his home internet connection (FiOS). It does not happen when he is on another network or if he used the GMail web interface. I see that when he uses Outlook his IP address is included in a header. He requested and got a new FiOS ip address but that did not help unfortunately. 

[#7]

Hi @mpvosseller 

I and some friends have same issue.

Cant send from a microsoft, ie outlook or hotmail etc as it goes to their spam.

Even when they accept as not spam, still happens.

I can reply to there email and it goes to their inbox.

some contacts in gmail this is there only contact, so I cant tell them to look in the spam box.

How do I fix this?

[#8]

Have any of these solutions worked for anyone? I think the issue has something to do with a Gmail issue and their new security update, rather than something that can be fixed via a setting change in Outlook. But I can't find any articles from Google regarding the issue.

[#9]

@MatthewMoran 

I have the same issue with 2 different customers.

All of them:

- use smtp.gmail.com:587/TLS (I tried 465/SSL) too;

- mail sent by the client outlook 2019 (no outlook 365) are marked as SPAM from many incoming servers;

- mail sent by Gmail's webmail are successfully sent

- SPF & DKIM records inserted into DNS server

Are there somebody that have found a solution?

Thanks

Michele

[#10]

Evenin Feb 2022 this problem persists. Anybody have any fixes yet?

[#11]

@EtterOps 

It seems I resolved the problem configuring the DKIM & SPF records into DNS server's domain provider.

Google webmail uses a different SMTP server than smtp.gmail.com

Ciao-ciao

Michele

[#12]

Hi mate, can you please share what exactly you did?

[#13]

Hi Sibirac,
my customers have registered their mail domain into a different provider than Google.
I set up the DKIM and the SPF records using the values generated by Google. Initially I setup these valuse for myself into a domain provider DNS but there was something wrong, so I used the technical support of the domain provider and they inserted these values for me. Now, the Google's tools give me the OK result.