Send mail to Office 365 via an Exchange Server hosted in Azure

Those of you who have attempted to send mail to Office 365 from Azure know that sending outbound mail directly from an email server hosted in Azure is not supported due to elastic nature of public cloud service IPs and the potential for abuse. Therefore, the Azure IP address blocks are added to public block lists with no exceptions to this policy.
To be able to send mail from an Azure hosted email server to Office 365 you to need to send mail via a SMTP relay.… [Keep reading] “Send mail to Office 365 via an Exchange Server hosted in Azure”

Free/busy Exchange hybrid troubleshooting with Microsoft Edge

Those of you who have configured Exchange hybrid with Office 365 before know that free/busy functionality can be troublesome at times and not work correctly.
Instead of searching through Exchange logs I found that you can pin point the exact error message through Microsoft Edge to assist with troubleshooting.
To do so;

  1. Open Microsoft Edge and login to Office 365 OWA ( with an Office 365 account
  2. Create a new meeting request
  3. Press F12 to launch developer tools
  4. Conduct a free/busy lookup on a person with a mailbox on-premises
  5. Select the Network tab
  6. Select the entry with “GetUserAvailability”devtools-getuseravailability
  7. Select the body tab (on the right hand side)
  8. The MessageText element will display the exact error messagedevtools-messagetext

Exchange Server 2016 in Azure

I recently worked on a project where I had to install Exchange Server 2016 on an Azure VM and I chose a D2 sized Azure VM (2 cores, 7GB RAM) thinking that will suffice, well that was a big mistake.
The installation made it to the last step before a warning appeared informing me that the server is low on memory resources and eventually terminated the installation, leaving it incomplete.
Let this be a warning to the rest of you, choose a D3 or above sized Azure VM to save yourself a whole lot of agony.… [Keep reading] “Exchange Server 2016 in Azure”

Exchange Server 2016 install error: “Active Directory could not be contacted”

I recently worked on a project where I had to install Exchange Server 2016 on an Azure VM and received error “Active Directory could not be contacted”.
To resolve the issue, I had to complete the following steps;

  1. Remove the Azure VM public IP address
  2. Disable IPv6 on the NICipv6-disabled
  3. Set the IPv4 DNS suffix to point to your domain. If a public address is being used it will be set to by default.dns-suffix

Once done the installation could proceed and Active Directory was contactable.

Completing an Exchange Online Hybrid individual MoveRequest for a mailbox in a migration batch

I can’t remember for certain, however, I would say since at least Exchange Server 2010 Hybrid, there was always the ability to complete a MoveRequest from on-premises to Exchange Online manually (via PowerShell) for a mailbox that was a within a migration batch. It’s really important for all customers to have this feature and something I have used on every enterprise migration to Exchange Online.

What are we trying to achive here?

With enterprise customers and the potential for thousands of mailboxes to move from on-premises to Exchange Online, business analyst’s get their “kind in a candy store” on and sift through data to come up with relationships between mailboxes so these mailboxes can be grouped together in migration batches for synchronised cutovers.… [Keep reading] “Completing an Exchange Online Hybrid individual MoveRequest for a mailbox in a migration batch”

Exchange Deployment in the Cloud

A little Introduction
Some organisations, would still prefer hosting their own Exchange server(s), rather than migrating to Office 365. And since the Cloud is the way to go for many organisations, deploying an Exchange server in the Cloud, be it Azure or AWS, could be challenging on so many levels. This includes latency, failovers, data disk corruption, replication and so forth.
If you’re unsure on how to start, unfortunately Azure does not provide a free test drive for Exchange server (as of this writing).… [Keep reading] “Exchange Deployment in the Cloud”

Complex Mail Routing in Exchange Online Staged Migration Scenario

Notes From the Field:

I was recently asked to assist an ongoing project with understanding some complex mail routing and identity scenario’s which had been identified during planning for an upcoming mail migration from an external system into Exchange Online.
New User accounts were created in Active Directory for the external staff who are about to be migrated. If we were to assign the target state, production email attributes now, and create the exchange online mailboxes, we would have a problem nearing migration.… [Keep reading] “Complex Mail Routing in Exchange Online Staged Migration Scenario”

Exchange Online Protection Organizational Approach

I have been working for an organisation who had recently migrated to Exchange Online protection (EOP), and we had found that some of his important emails, from a legitimate email source, were getting blocked.
Upon investigation it turns out that a week before the customer’s organisation was hit by a Zero-Day virus which resulted in spoofed emails coming through and landing in the end user mailboxes. This resulted into a bit of chaos and a decision was taken to modify the Bulk email threshold (BCL) to a tighter level.… [Keep reading] “Exchange Online Protection Organizational Approach”

Understanding Outlook Auto-Mapping

Auto-mapping is an Exchange & Exchange Online feature, which automatically opens mailboxes with Full Access permissions in a delegate’s Outlook client. The setting is configurable by an Administrator when Full Access permissions are assigned for a user. Once enabled, the periodic Autodiscover requests from the Outlook client will determine which mailboxes should be mapped for a user. Any auto-mapped mailboxes with be opened by the Outlook client in a persistent state and cannot be closed by the user.… [Keep reading] “Understanding Outlook Auto-Mapping”

Exchange in Azure: NIC disabled/in error state

I recently had the need to build my own Exchange server within Azure and connect it to my Office 365 tenant.
I loosely followed the steps in this Microsoft article: to get my Azure (ARM) VMs and infrastructure deployed.

I initially decided to utilise an A1 Azure VM for my Exchange server to reduce my costs, however upon successfully installing Exchange it was extremely slow and basic things like EAC and creating mailboxes would not function correctly due to the lack of resources.… [Keep reading] “Exchange in Azure: NIC disabled/in error state”