Forum Discussion
messg spam from my office email to yahoo
It seems like until someone at Microsoft wakes up and fixes their reputation or whatever else is causing this issue, we are all stuck in the middle of the end users complaining their emails aren't getting delivered and hoping the recipients will add the sender to their address book (which kind of works).
Has anyone found a reputable smtp relay service that is compatible with 365/Exchange Online? I had thought I'd just route outbound mail through SendGrid till this gets resolved, but that requires a password on the send connector and I'm not aware of any way to specify a password on the send connector with Exchange online.
I suppose the problem with a service that works without a password is that in theory is a quasi open relay and it would take anything from your domain and deliver it. If that service was more basic and didn't touch the email, DKIM signing from MS should continue to work to differentiate legitimate from illegitimate email, I think.
- I'm actually about to set up with SendGrid as their salesperson stated that, people have used their services as an SMTP smart host with O365 services in the past..
Though a sales person from SMTP.com said the same exact crap, and I ran into a similar issue where IP Auth can only be used with O365 with their services. Though they also don't take DNS entries or IPv6.. Their support team also don't seem to have a handle on how email works either, and don't understand the concept of what we are doing here. Hopefully, I don't have a repeat with SendGrid.
But I think our only option is to setup this client with proofpoint or a 3rd party outbound spam filtering service, to circumvent this issue. As it seems like these SMTP relay companies are pretty old school with their methods, and were developed with email marketing in mind, not as a true SMTP Smart Relay.
It is extremely unfortunate that no one on Yahoo or Microsoft(even though I don't this its their problem) is taking accountability for this issue. Nor is this issue getting the attention that it deserves. For an entire month, this has been going on, with no resolution in sight. Wish I could be this incompetent at my job.- NLart, please keep us posted if SendGrid is able to support this, as they told me they don't have any possibility to accept a connection without credentials. The alternate way is to connect my "application" with Zapier. If someone from SendGrid is reading this, see ticket 8823518.
As you mentioned these smtp relay services were setup to send messages from applications, not a full scale smtp smarthost.
Of everyone I reached out to, smtp2go had the best response and gave me an immediate solution.
Proofpoint or something is certainly an option as well, but likely at additional per user costs. We've used services like that in the past, but have been trying to get all in on 365. However, if Microsoft doesn't even care to address a huge problem like email deliverability, it does make you wonder if we are moving in the correct direction.- Unfortentually we didn't go with sendgrid.
They flagged my signup as suspicious, and after wasting 2 days with their support, and them coming back with, "Please provide your LinkedIn info to verify your identity" made me just switch to proofpoint. SMTP2GO was another option, and they "said" you can use their API with O365, their documentation was very generic, and just went over the API on their side without vetting any configuration with O365. I don't think the rep fully understood what I was trying to accomplish since why would anyone normally would want to send all their email out O365 through a SMTP relay service.
Just switched mail flow to proofpoint not too long ago for our client. Here what was found.
Sending from our mailbox in the customer's domain, that we previously stated not as spam in our att mailbox, ended up in the spam folder.
Sending email from a new or a mailbox we haven't tested with in the past, from the customer domain, does not end up in the spam folder to our att test mailbox.
We created a new mailbox at aol.com
Found that all emails went through without issues.
Coworker's yahoo mailbox also received the messages without issues from the customer's domain. At first it did end up in the spam, but appeared to clear up without his interaction with the second email. At this time I also stopped DKIM signing from Microsoft, and did it directly from proofpoint.
Had the CEO of the client email those three mailboxes, all went through, nothing ended up in spam.
(not related but for the lulz)
Emailed from my AOL test box and to my att test one, and vice versa. both ended up in spam lol
I don't have the complete warm and fuzzies considering how mail I once flagged as not spam, ended back up in the spam box. I'll take this improvement through. Will have to monitor it over the next few days.
Why do I think this isn't a Microsoft problem?
Because the client also uses a 3rd party website used for volunteer signup.
While I do have to address this with the end-user who manages it. While the From domain, sends out with the website's domain name, the reply to is set to the customer's domain. This voulentier sign up a website also doesn't support DKIM, thus I see the fails in my DMARC reports for DKIM from yahoo.com, and co.
But yet.. all of that mail goes through and gets to yahoo.com's inbox, even though its failing DKIM. I only have DMARC in reporting mode at this time until I can clean it up.
So scottchester it seems like we were able to get around this problem using a spam filtering service that can filter/relay outbound. While more costly than a SMTP relay service, I at least have emails that would of ended up in the spam folder, in the inbox now.
Though while I don't think it would be the case here. Are all of you that are having issues signing DKIM outbound from O365? As at first, I figured I was going to have mix results with this until I removed DKIM signing on microsoft's side and just had Proofpoint doing it. It actually made a difference. Could be nothing and just things straightening its self out from the changeover, as I can't see why a DKIM signature from Microsoft in the message headers would trip yahoo mail services to flag it as spam..
But at this point, if mail gets to the inbox for yahoo mailservices domains. I really don't care what it was lol
NLart I think most of us know and understand that MS is not to blame here, but that being said, this is an issue with deliverability between platforms, and the platforms should work together to get this resolved. It is in both parties best interests to do this. This is why I and others keep calling on MS to step in from a Product Level with the Exchange Team to deliver us timely updates on what is being done through platform intercooperation to solve the issue.
- I did find a service that it seems possible to route outbound mail through to solve the delivery problem to yahoo and others, at least until MS fixes this. The issue is that because MS doesn't allow any kind of authentication on the connectors, you're going to somewhat open yourself to signing mail that might not be legitimate if someone determines the correct information.
That being said, if you're desperate for a workaround in the meantime, check out smtp2go. They will allow you to whitelist specific sender addresses and then they will act as an open relay for that mail. (After you go through the proper setup, authenticate the domain, etc.)
Most services won't seem to work as they want some way to authenticate the email with IP or password.- Hi.
We are doing similar things. We have a gravity zone acct and i just routed email destined to yahoo addresses through that service for now. This does seem to get the email to the inbox on yahoo instead of spam.
We also have an smtp2go account and i will try the address auth option for the next tenant that asks for a fix.
I don't really know whose issue this is, presumably it's a spam filter update on yahoos side. I'm curious why some believe this to be Microsoft's problem. Is it based on the HELO/EHLO issue? I haven't seen a change in my headers over the past month that indicates anything changed, but maybe I'm missing something? Just curious. scottchester
profputr I'm pretty convinced this is NOT Microsoft's fault. I have run multiple tests from various email sources, and only Microsoft's email gets processed as spam.
I also turned on DMARC reporting on two different servers (one Microsoft, one non-Microsoft) and sent email to Yahoo from those services. Both DMARC reports came back with all messages as 'PASS'. Yet again, only email from Microsoft went to spam.
Here is my suggestion to everyone: Start sending messages to people in tech media about this.
