Odd issue with Exchange 2013 & Outlook 2013 (and OWA) with regards to mail being sent as spam

[xbamaris]

I'm having a weird issue with Outlook 2013 and OWA sending email that is marked as spam...

 

 

My Exchange server's IP has everything set up correctly, PTR, SPF(as I host for a few different domains with Accepted Domains configured properly)

 

 

I can receive email on all of the different domains.

 

 

However, when sending an email from Outlook 2013 and the OWA, it is marked as SPAM by Gmail. (5.7.1) 

[MorganX]

Have you checked your IP to see if it's on any blacklists? mxtools ... If it was SPF related the mail would get rejected, not tagged as spam.

[Praetor]

Just gmail marks it as spam? Can we se the message?

[sc302 Veteran]

The ptr record is incorrect, the email domain does not match the domain being sent as, or there is some other issue with dns that has propagated to gmail yet.  You will need to look at your mail header to determine what is going on.  You will be able to determine what it is pretty quickly once you do.