TLS with MAC mail

Hi All

Please note we have managed to get SPF and dkim configured for our domain. Our ISP supports TLS. Our main issue is that MAC is used by our principal and it does not work on it. I have tried many different options in mac but i was unable to get it to work.  This works well in windows environment without any issues

What happens?
After setting up mail on MAC using mail with my exchange server all emails that the user sends goes to junk. have tested with  2 different users same thing.

Why does this happen? Upon investigating further the mail headers show that the spf and dkim had a pass but it still ends up in spam of the user been sent to. In advanced settings under accounts i see an apple certificate. I suspect this might be an issue. Is there any settings that i am missing out
Member_2_6474242Senior Systems AdministratorAsked:
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Peter HutchisonSenior Network Systems SpecialistCommented:
Open KeyChain Access  on the Apple Mac and make sure that any root and intermediate certificates using by DKIM are installed and configured as 'trusted' to access mail through your mail system.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
Jian An LimSolutions ArchitectCommented:
Principal = UserA
Principal use MAC

when UserA use windows outlook, send email - userB received in inbox
when UserA use Mac outlook, send email - userB received in junk

i am saying this correctly?
Peter HutchisonSenior Network Systems SpecialistCommented:
Maybe the Outlook client on the MAc has Junk mail enabled or has some client side rules enabled.

See Tools, Rules.
See Tools, Junk Email Preferences
Outlook Preferences -> Rules and Junk.
Creating Active Directory Users from a Text File

If your organization has a need to mass-create AD user accounts, watch this video to see how its done without the need for scripting or other unnecessary complexities.

Jian An LimSolutions ArchitectCommented:
Outlook client on the MAC don't have client side rules.
Member_2_6474242Senior Systems AdministratorAuthor Commented:
Hi Jian

Any email that is sent from MAC to external ends up in junk. e.g. or, . The user is using Mail on mac

As for your query
Principal = UserA
Principal use MAC

when UserA use windows outlook, send email - userB received in inbox
when UserA use Mac outlook, send email - userB received in junk

i am saying this correctly? yes you are correct
Jian An LimSolutions ArchitectCommented:
Assume the situation is correct, we can know is the Mac OUtlook who cause it, not the backend.

When you compare the Message header on both, how much difference is this? the best is if you can attached it here so we can view it.

Is this the same result on the user in gmail, yahoo or hotmail?

What version of OUtlook MAC you are using?
Mac 2011 ? or 2016?
Member_2_6474242Senior Systems AdministratorAuthor Commented:
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.