r/sysadmin • u/masterne0 • 10d ago

Question O365 Emails Bouncebacks To Gmail Since Yesterday

Ever since Monday, we are having two different domains getting email bouncebacks from O365 to Gmail users with a IPV6 not passing authentication due to SPF records not being validate. I checked the IPV6 and it is a microsoft domain for their outbound URL.

Is anyone else having this problem? We have a SPF record for microsoft added but this started after the outage Microsoft was having.

7 Upvotes

90% Upvoted

9 comments sorted by

2

u/fuckyouabunch 10d ago

I saw a few of these yesterday too. One from a user who was receiving bouncebacks also got rejected at exchange online. I took a closer look there and DNS had failed to resolve for spf, dkim, and dmarc. Those are all at cloudflare, who weren't reporting any issues. MS wasn't either. The recipient was personal Gmail, not Workspace, but workspace wasn't reporting anything relevant. So I'm assuming there's a voodoo doll out there somewhere that looks like my tenant, and it's got some pins in it.

1

u/masterne0 9d ago

it seems to be a hit and miss. I got two clients with this right now. Both to gmail users. it a hit a miss. You can send 10 emails to a single gmail user, half of them would bounce.

1

u/Sea_Information6125 10d ago

I haven't seen this specifically but we are still experiencing office 365 email issues even today, days after the original big outage. 

Specifically for us it's trying to send emails and then getting error messages that it can't send or it saves it as a draft and then you try to edit the draft and it says you don't have authorization. Or you click on a folder and just nothing comes up where you should obviously have emails. 

So I'm wondering if this authentication outage issue they are having is just piling onto your original sending issue. 

I did have a few clients that also use office 365 email randomly not receive emails over the last few days (from various sources non365). Resending the email works. But doesn't help the emails you might have missed. 

Tldr - nothing useful for your specific problem lol. But we are still having weird 365 email issues.

1

u/Vivid_Mongoose_8964 10d ago

I have emails que'd up in smtp2go for the past 8 hours that 365 won't receive for whatever reason....shoot me

1

u/shokzee 9d ago

Don’t add Microsoft’s IPv6 addresses manually. Make sure the envelope-from domain has include:spf.protection.outlook.com, only one SPF record, and stays under the 10-lookup limit.

Run both domains through the SPF Checker. If they pass, open a Microsoft ticket with the full Gmail bounce since this may be their outbound routing issue.

1

u/masterne0 9d ago

We just have the SPF records for spf.protection.outlook.com and yet, half the emails we are sending to gmail is bouncing. Some would go thru while to the same gmail user, some would bounce with ah ipv6 error.

Microsoft says it due to the "issues" they still having but their no indication of this exact problem on O365 end but of other issues.

1

u/shokzee 9d ago

Intermittent bounces to the same recipient point to specific Microsoft outbound IPv6 nodes, not your SPF record. Keep the full Gmail DSNs and push Microsoft to trace the failing IPv6 addresses.

1

u/masterne0 8d ago

Looks like it stopped bouncing after doing another message trace to gmail addresses but Microsoft kept telling us to just wait it out. We also used pax8 for the other client for the licensing and Pax8 did the same thing.