Office 365 Hybrid Setup Problems :(

[2097]

Started to Deploy Full hybrid setup for O365 due to more and more people using Teams and i imagine eventually we will have to go "Full" O365.

 

I ran the full setup and it didn't give me no errors at all.

 

But ! i do have problems

 

1.) Any user with an exchange online mailbox cannot email internal on-premises mailboxes . It gets stuck in pending. Non-internal users it does use Microsoft's own servers and it works fine.

 

2.) This was done for teams , but seemed to have buggered it up even more . Teams will now not save the calendar meeting to their calendar. They can still see their on-premises calendar though.

 

With regards to the emails , Looks like online exchange is trying to send internal emails via port 25 to our domain name. The problem being we do have a SMTP spam filter ( GFI ) on port 25. Has any one set this up without a Internet facing internal exchange ?

[3s-gtech]

Have the send connectors for internal (same domain) connectors set up correctly? Are they showing in the ECP for both?

 

Calendar can be a challenge. Do you have autodiscover set up and working back to your Exchange?

[2097]

regarding the connectors , it does look like its forwarding emails to onsite port 25 ( which all emails do )

 

But For o365 to internal emails i am getting this error

 

Reason: [{LED=450 4.4.317 Cannot connect to remote server [Message=451 5.7.3 STARTTLS is required to send mail] [LastAttemptedServerName=mail.MAILSERVER.org.uk]

 

Im assuming this is because its trying to send emails to our on premise via port 25 .. Which is our GFI spam filter.

 

Any way around this ?

[3s-gtech]

Are your Exchange certs valid and in date, for send and receive? If you email a GMail address from an internal mailbox, does it show the padlock in the message headers?

[2097]

OK think i figured it out thanks to you and your comments on the send connector.

 

Removed the default send connectors on exchange online -

 

Created a new one , pointed it to GFI port 25 onsite - Removed the need for TLS encryption.

 

On GFI IIS SMTP , added an allowed relay "Outlook.com"

 

Inside GFI , i could then see all the emails coming in . Had to modify the settings for header verification.

 

Once this is done emails and calendar setup now work ( i assume calendars wasn't working because it couldn't send the emails out ? )

 

 

 

Now i just need to do it the other way ... Internal and external to O365 accounts

[chaplic]

This is not correct. O365 <> Exchange requires no other email server in between them. Yes, you can ship mails but you'll start noticing things won't work

 

Try setting an internal and external Out of office on a O365 mailbox then mail it from exchange mailbox- you'll get the external reply.

[2097]

This is not correct. O365 <> Exchange requires no other email server in between them. Yes, you can ship mails but you'll start noticing things won't work

 

Try setting an internal and external Out of office on a O365 mailbox then mail it from exchange mailbox- you'll get the external reply.

 

lucky we are not migrating any mailbox yet

 

i just wanted team implementation to work better , which now it does.

 

How have other schools done this ? surely im not the only one on hybrid with a spam filter.