#exchange 2003

Decide on Office 365 Migration Path

Deciding on the best migration path of your users’ email to Office 365 can be difficult. Your migration performance will vary based on your network, existing messaging systems design, mailbox size, migration speed, and so on.

For migrations from an existing on-premises Exchange Server environment, you can migrate all email, calendar items, tasks and contacts from user mailboxes to Office 365. The…

Mailflow Co-existence between Hosted Mail and Office 365 during IMAP Migration

This article will explain how to create mail flow coexistence between disparate IMAP source and Exchange Online destination.

Use case:

Customer wants a mailflow co-existence between hosted email e.g. Gmail and Exchange Online during mailbox migration phase.

Customer has on-premises Exchange Server but does not want to create hybrid environment or have a situation where hybrid configuration is not…

A large City in the Phoenix area was on a deadline to upgrade their Microsoft Exchange environment, and reached out to Sentinel Technologies to help them design, upgrade and migrate their Exchange and Active Directory.

The driving factor for this project was that the City was on Exchange 2003, which had a an End-Of-Support date of April 2013. Additionally, they had accumulated multiple Exchange organizations (2003, 2007, 2010) over the years, creating an inefficiency in interoperability. The latter issue presented an opportunity for Sentinel to move their physical Exchange server environment to virtual servers (P2V) with VMWare, effectively cleaning up their environment through the consolidation of their users to a single Exchange organization.

Sentinel Technologies first delivered a comprehensive design of what their environment should look like once the entire environment was migrated to Exchange 2010. Once the City approved the design, the project was scheduled via Sentinel's Project Management. The implementation process began with the preparation of the virtual environment, upgrading the Exchange, migrating the data of their 2000 mailboxes; continuing through to the connection and configuration of the supporting equipment (backup software, email filtering appliance, Citrix Netscaler load balancing appliance, SAN storage), the testing and verification of performance, and the decommissioning of the old Exchange environment.

The result was an email environment that was more efficient, easier to manage and came with the availability of new features, such as Multi Mailbox Search and the Exchange Control Panel.

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First we need to verify that port 25 is working.

Try telnet outbound.mailhop.org 25

If you can't connect, try again using another port.

ehlo <your domain>

If there isn't 250-STARTTLS then something is not right. Try again using another port (e.g. 10025)

The actual configuration

Leave "Default SMTP Virtual Server" as is. Revert all outbound security and smart host configure. Only change outbound connection TCP port. (For more information on how to change please google for Microsoft Knowledge Base: 274842 How to change SMTP port 25 to another port in Exchange 2000 and in Exchange 2003. 

Create new SMTP Connector.

On the General tab, provide an appropriate identifying name for the connector. I used the name ‘SMTP Smart Host Relay for DynDNS Connector’.

Choose to use DNS or forward to a smart host.  Enter ‘outbound.mailhop.org’ or you use the IP address of the smart host in square brackets. [63.208.196.171].  I would enter the FQDN rather then the IP address

Under Local Bridgeheads, click Add. Add the server that becomes the bridgehead server for the routing group. Designate an SMTP virtual server as a bridgehead server for the SMTP connector. This can be either the server that you are working on or another server in the same routing group. Alternatively, this duty can be shared by multiple servers.

Click the Address Space tab. Under Connector Scope, click either Entire Organization or Routing Group. As in earlier versions of Exchange Server, when you configure the Internet Mail Service, click Add, click SMTP, and then click OK. Accept the default (*) unless you require outbound e-mail domain restriction, and leave the cost as 1. If you have accepted the default of (*), you should never click to select the Allow messages to be relayed to these domains check box. Clicking to select the Allow messages to be relayed to these domains check box would open your server for relay to the world. The Allow messages to be relayed to these domains check box should be for secure domain to domain connections only.

If you have chosen forward all mail to a smart host, click the Advanced tab. Click the Outbound Security option, and then select an appropriate authentication method for your relay host. The default is Anonymous Access. You must change this to Basic authentication (password is sent in clear text).   Now click the Modify button.  Now you must enter your DynDNS user account information.  Enter your DynDNS user name and the password.  Then confirm the password.  Check TLS encryption. You don't need to use "SMTPS (SSL/TLS)" port if you enable TLS encryption. You can use port 25/10025 and TLS altogether. (Given that the server response with STARTTLS in the previous steps) NOTE: If there is an error here under your connector you won’t be able to send email out.  Mail will be stuck in the queue.

The article said you need to restart Microsoft Exchange Routing Engine service and Simple Mail Transfer Protocol (SMTP) Service but in practice, I didn't have to restart anything. (Exchange 2003)