Email to new recipients going to spam

[tek9]

Hi all.
One of my customers has been having issues lately, for the past few weeks or so, where emails being sent to new recipients, i.e. someone they've never sent an email to before, is either going to spam or not being delivered entirely. If they send an email to someone that has already received an email from their domain prior, there's no problem, but if it's someone that has never received an email from their domain, it's spam.
Their email is Office365 hosted by GoDaddy.
They're a small catering company, and most, if not all, of those emails that are being flagged, are simple emails with basic text and the subject "Event Menu", so nothing fishy over there, with 2 or 3 small PDF files with their menu and pricing. They say that they've been sending this same email for the past 2 years and it only started being flagged for the past few weeks.
I checked and their domain isn't on any blacklist. They also sent this same email to the random address generated by the website isnotspam.com and it came back clean.
Any ideas what else to check?
Thanks.

 

[nlinecomputers]

Many places block PDFs outright. That is THEIR policy and not yours. Best to put that pricing on the website and put links. You send a PDF to me and my spam filter will nuke it. Too many viruses out there.

 

[nlinecomputers]

The other things to do are to setup SPF, DKIM, and DMARC. So that your emails are digitally signed. That will make most spam filters rank you higher. If they are sending Advertising out then they should use a service like MailChimp.

 

[tek9]

These are emails going to various email addresses, mostly to Gmail, which as far as I know does not block PDFs. I had her send it to me, and I'm using Google Apps, and it came through OK.
SPF settings are in place as with most other Office365 domains, and if I'm not mistaken, that report from isnotspam.com listed a DKIM record.
These are not advertising emails. These are in response to people calling them asking about pricing and menus etc. It's not mass emailing. One at a time.

 

[nlinecomputers]

Check the domain on mxtoolbox.com. Unless you can see the headers of an email that has been marked as spam you are only guessing.

 

[Sky-Knight]

Ditto the mxtoolbox check, sounds like you're on a black list. OH, and good luck fixing it! Only idiots use Godaddy hosted O365, this is just the tip of the nightmareberg you're going to be living with until you get them out of there.

 

[Markverhyden]

You need to make sure and get the DMARC done as well. To be clear, they are actually using Exchange and not Godaddy host iMAP.

 

[tek9]

I checked mxtoolbox multiple times, was the first thing I checked, they're not blacklisted.
They're on O365 via GoDaddy, not IMAP.

 

[Sky-Knight]

O365 via GoDaddy means they're in Godaddy's private section of O365, which often gets black listed for the same reasons Godaddy mail used to.

Meanwhile, you have no admin tools to fix stuff yourself... no ability to access that tenant to protect your client from anything... you cannot access the Azure tenant either so all the AAD stuff that's coming down the pipe is inaccessible AND your client is paying more than the MSRP full retail for O365 to get there.

They are paying more... for less... The local telco out myway does the same thing... GET THEM OUT OF THERE!

You should be able to look at the SMTP logs and KNOW why someone rejected the mail... but you can't.. because Godaddy is in the way. The entire reason you don't know what's going on here is GODADDY!

I cannot emphasize enough just how much every MSP on the planet should be pushing to get their customers away from that nightmare. And every day that goes buy, every new feature MS bolts onto 365, the worse the value prop gets.

 

[YeOldeStonecat]

I agree with NLine and Mark...double check their DNS records. Ensure SPF, DKIM, and DEMARC are solid 'n proper.
And I agree with Rob (Sky Knight)...GoDaddy sucks for email...they block access to much that you should be able to do in the Admin panel, so you, as the IT people for your client, are stuck not being able to do much at all.

Move 'em under your own CSP or if you don't do CSP (why not if you're in the IT game?) have them go direct..so at least you'll have an Admin account where you can get in and effectively admin things.

 

[tek9]

I do have a CSP account with a few customers under it. This particular client did their account on their own, so just trying to help them along. I just quoted them a migration project for this, but am not looking forward to it. The little googling that I did on moving away from GoDaddy's O365 shows that it might take them a while, after a few phone calls, for them to remove the domain from their account.

 

[Sky-Knight]

I wouldn't rely on Google too much, that standing issue with Godaddy has generated considerable friction between Godaddy and Microsoft, and as a result Godaddy has responded with better training.

So it's easier to move people today, than it was even a month ago. But you do still have to plan for the worst of course.