Mail Routing in o365.

Quick question about mail routing in O365.

Once we have migrated all mailboxes to cloud this is how we would like mailflow.

External email comes in to cloud mailbox,user responds and mail is sent out.  O365 routes outbound mail to On-Prem mailbox Server, mail server attaches signature  (Exclaimer Mail util is sitting on both MBX servers on prem) mail server routes back to o365 then out to the internet from there.

I have asked MS this same question and get 17 diff answers.  can anyone shed some light.
jgutierr76Asked:
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Adam FarageEnterprise ArchCommented:
Its a tad bit more complex unless you setup a send connector between both sites. The issue with this is that it might be brought up as a mail loop.

Do you still have an on-prem Exchange organization?
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jgutierr76Author Commented:
We are currently in a Hybrid setup so yes to On-Prem, the only solution MS is giving us ATM is to send mail to internet direct from mail server.  Doing this though we would lose the secure email function using a key word in subject line.
The other option is to have mail sent direct to us from web which would kill us due to the amount of spam we get.

We seem to be stuck be between the proverbial rock and hard place.
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Gareth GudgerCommented:
Have you seen this document. Seems like they have a setup guide of getting Signature Manager to work in Office 365.
http://docs.exclaimer.com/Signature-Manager-With-Office-365_Worldwide.pdf
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jgutierr76Author Commented:
thats it.
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