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We will be migrating about 2000 users to Office 365. How do you prepare the Hybrid Server? I suppose this should be new Exchange server with no mailboxes and just the CAS role (Exchange 2016) and not part of the DAG.

Lets say I set up two Hybrid servers (VM) with 2-4 cores, 8-12GB of RAM, and 100GB of disk space and install the SSL certificate - same one used across the Exchange org

How do I create a DNS namespace eg. hybrid.abc.com and publish this to the public DNS?

Is this the namespace I need to put in as the FQDN name in the HCW setup?

I suppose this namespace - hybrid.abc.com needs to be in the certificate SAN?

Can I add multiple hosts A record for hybrid.abc.com in the public DNS if I have 2 or more hybrid servers?

Do I need to manually create the send connectors on the Hybrid servers to my Trend Micro IMVSA? This is the first hop, after Trend IMVSA, the next hop is the Cisco Email Security - our mail gateway to the internet. We have a Edge transport (ET) server for address rewriting for outgoing mails only. We will pass the address rewrite job to the Cisco instead.

Should I create a bypass in Trend IMVSA for hybrid traffic since this is only meant for mailbox migrations? create a rule a rule to bypass all traffic from hybrid server to Office365 endpoints?

How do I make sure that the Hybrid servers only do mailbox migrations and it will not process any email traffic?

Thanks

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Why do you want the hybrid server to bypass the mail traffic? It is not common.

You could try Exchange Server deployment assistant. https://technet.microsoft.com/en-us/exdeploy2013/Checklist?state=3229-W-AAAAAAAAQAAAAAEAAAAAAAAAAAAAwAMAAAA~

The migration is a complex process, you may review the following official documents to prepare an overall plan.

First you need to do some prerequisites before you config a hybrid deployment. For example: AAD Sync, custom domains in O365, server role (Exchange 2016 and newer: At least one server that has the Mailbox server role installed) and so on. https://docs.microsoft.com/en-us/exchange/hybrid-deployment-prerequisites

Next, create a hybrid deployment with the Hybrid Configuration wizard. https://docs.microsoft.com/en-us/exchange/hybrid-deployment/deploy-hybrid

Last, you then could move your mailbox to Online.

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