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 (https://outlook.office365.com/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 reddog.microsoft.com by default.dns-suffix

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

Programmatically read email from an Exchange Sever Mailbox

I can’t recall how many times I have come across a requirement to programmatically read emails from an Exchange Server mailbox and take some action based on the presence of new messages. The component reading the emails can read the mail content, parse its contents and transmit the data to other downstream systems. In this blog I’m going to take a look at one way we can do this.

Objective

In my scenario there was a requirement to develop a program to retrieve mails from an Exchange mailbox and, based on a specific criteria, send the email to multiple users based on an distribution list identifier.… [Keep reading] “Programmatically read email from an Exchange Sever Mailbox”

Securing Emails Outside of Your Organization With Office 365 Message Encryption

​For those of you who have been concerned about email security for a number of years, you may remember a solution from Microsoft called Exchange Hosted Encryption (EHE).  This was a cloud based service which allowed organizations to encrypt emails according to certain defined rules.  For example, you could encrypt emails where the intended recipient was outside of your organization and certain keywords or regular expressions where detected such as a credit card number.  This was a very useful service for protecting emails sent to ANY user, regardless of the relationship with the user’s company. … [Keep reading] “Securing Emails Outside of Your Organization With Office 365 Message Encryption”

End User Access To Spam Quarantine in Office 365

One of the ​features of Office 365 which gets very little attention is Exchange Online Protection (EOP). EOP is a Microsoft cloud service which protects Exchange Online in Office 365 from spam and viruses. EOP is a built-in capability of Office 365. There is no additional license required to use it.

Emails which EOP detects as spam are trapped in a quarantine area. Users were notified that email was quarantined by an automatically generated email message from EOP.… [Keep reading] “End User Access To Spam Quarantine in Office 365”

Exchange Online Inactive Mailboxes

In an enterprise deployment of Office 365 Wave 14, one of the recurring pain points was how to handle mailbox data retention once a user left the business and the data is required for compliance purposes. There were a number of options available to handle this:

  • Leave the mailbox in-situ and disable the user account
  • Change the license SKU to Kiosk Plan 2 as it’s a cheaper license cost and disable the user account
  • Migrate the departed user mailbox back to the on-premises hybrid Exchange platform
  • Use a 3rd party cloud archive solution

While all of these will work, on an enterprise scale they’re quite clunky and even with an identity management solution in place, they’re not particularly practical or cost effective.… [Keep reading] “Exchange Online Inactive Mailboxes”