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Posted (edited)

Just got home, and glad to see you managed to sort it!.... :-) I was in the middle of driving on the motorway so my hands were pretty tied!

 

It's quite a common thing people having issues with receiving email between O365 & Hybrid Exchange Server when setting this up, always down to 1 setting being out of place! :-) and it's generally down to the configuration of the receive connector :)

 

James.

Edited by EduTech
Posted

Potential, only if you're concerned data not being sent via TLS.

 

If you are then I would work on the issue and enforce TLS.

Posted
Potential, only if you're concerned data not being sent via TLS.

 

If you are then I would work on the issue and enforce TLS.

 

It is recommended that you enforce TLS so that when you send/receive between your On-Premise & Cloud Recipients the communication is secure, just like if it was internal. You wouldn't allow mail to be routed around your internal infrastructure unsecure would you? so why do it in this scenario.

 

I would look into the reasons as to why you have an issue using TLS, I would imagine it's something to do with the SSL Certificate being used as in FOPE it will have a rule which states...

 

The Security.. which generally is setup as follows (certificate Subject Name Matches X)

Image11.PNG

 

and it routes email via smarthost (which points to the Public IP of your Hybrid Server)

Image12.png

 

James.

Posted
It is recommended that you enforce TLS so that when you send/receive between your On-Premise & Cloud Recipients the communication is secure, just like if it was internal. You wouldn't allow mail to be routed around your internal infrastructure unsecure would you? so why do it in this scenario.

 

I would look into the reasons as to why you have an issue using TLS, I would imagine it's something to do with the SSL Certificate being used as in FOPE it will have a rule which states...

 

The Security.. which generally is setup as follows (certificate Subject Name Matches X)

[ATTACH=CONFIG]20879[/ATTACH]

 

and it routes email via smarthost (which points to the Public IP of your Hybrid Server)

[ATTACH=CONFIG]20880[/ATTACH]

 

James.

x

 

I agree but it's down to the company if they want to send via TLS. There 10,000 companies I know who still use SMTP without TLS. Most finance sectors do as its a requirement but many O365 customers still don't.

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