During many Exchange projects (On-Premises or in the Cloud) we see a lot of situations when organisations create an additional mailbox (secondary mailbox) for some users. Everybody, who works with Exchange environments, knows that a mailbox could have multiple email addresses associated with it. The question is always, why not just define an additional email as an alias to the mailbox? Of course, this scenario could work in some use cases. You probably think, it’s OK…

However, when someone sends an email to the address that defined as an alias, the recipient is not going to easily see to what email address the email was sent (in more details down in this blog post). Also, when we only use aliases, all emails that we send are always seen as if they were sent from the primary email address associated with the mailbox.

We all know that  pictures explain better than 1000 words, so let’s take a look. Because of this, let’s see how to do this On-Premises and in the Cloud (Office 365).

The “Challenge”

The following image illustrates that I have multiple email addresses associated with my mailbox:

Multiple Email Addresses (eMail Aliases)

When someone sends me an email to one of my addresses, let’s say to InterruptYourVacation@iRangers.com 🙂 , of course it will arrive at my main mailbox.

Email in the mailbox

 

As  you can see, the email arrived. And… do you see the first issue?! At least it bothers me! 🙂 … If I look on the line “To:“, I see that this email was sent to Misha Hanin. When I double-click at the name I see the following screen:

Contact Details

 

Yes, it’s not clear to what address the email was sent! Of course, I can go and check “Internet headers” and I will see something like this:

 

Internet headers

 

I don’t know about you, but for me going and checking headers for all emails, every time when I need to know to what address it was sent to is too much :)!

And, this is only the first part of the problem!  In addition to this, we also have a “challenge” to use “Send As” functionality!

Let’s try to “Send AsInterruptYourVacation@iRangers.com. So, logically, many of us will try to do something like this:

 

5

 

or

 

Send As

 

Now, let’s see how I will see this email when I check my @highclouder.ninja mailbox:

 

Send As - Wrong

 

Seems like, ALL my attempts to send emails as  InterruptYourVacation@iRangers.com were ignored and as a result, this email looks like it was sent from misha.hanin@irangers.com (this is the primary email address of my corporate mailbox)!

Therefore, exactly at this moment, many companies decide to create an additional mailbox (in my case it should be InterruptYourVacation@iRangers.com) and configure “Send As” permissions.

It’s nothing wrong with this approach, however, as a result of this decision, now you have to manage multiple mailboxes (I even not touching the licensing topic yet!).

HOW EXPERTS WORK WITH MULTIPLE EMAIL ADDRESSES

So, when our clients deal with this “Receive As / Send As” problem, we, at iRangers, do the following:

  1. Create a new Distribution Group. As a Primary Email address for this group we define an address that we want to use as “Receive As / Send As
  2. We add required users to this new Distribution Group. So, in My case, I added myself (misha.hanin@irangers.com) to this group. Now, all emails that will arrive to address InterruptYourVacation@iRangers.com will be forwarded to misha.hanin@irangers.com
  3. Assign “Send As” permissions. By doing this, misha.hanin@irangers.com will be able to Send As: InterruptYourVacation@iRangers.com

I hope you know how to do all this by using GUI, therefore let’s see one of the ways how to do this in PowerShell (first of all, If you are in the Hybrid Mode, you will need to do all steps, from On-Premises and Office 365 sections):

On-Premises:

Also, we can try to allow the Group itself to Sen-As (Sometimes this doesn’t work. So, please consider this command just as a reference):
For a validation:

Office 365:

Before moving forward, be sure that Azure Active Directory Connector (AADC) has already synchronized all data. Of course, you can force the sync by executing the following command from the AADC server:

(iR-Sync01 is our AADC server. And…., Yes, I am lazy… I am connecting to my AADC server with remote PowerShell… )

Now, when all objects get synced to the cloud, let’s connect to Office 365 and execute there a few commands. Here is how we connect to the Office 365:

OK, now as a result of the previous steps, we are inside O365 PowerShell session. Let’s run this commands:

In addition, for a validation purposes:

In Conclusion

Now, after all those steps, let’s repeat Receive As and Send As exercise  :). First of all, I will send an email to InterruptYourVacation@iRangers.com

And… Voila! As a result of all our hard work 🙂  email was automatically forwarded to my primary mailbox: misha.hanin@irangers.com and …in the “To” field I see that this email was sent to InterruptYourVacation@iRangers.com:

 

Recieve As

 

We are almost at the end :). So, I think this is a time for the last test. Now let’s Send as: InterruptYourVacation@iRangers.com

 

Send As - Working

 

Yes, here is the result we were looking for!

 

Send As / Receive As

 

Finally, I hope you find this blog post informative.

Don’t hesitate to contact me via contact form or be in touch through iRangers.com

Cheers,
Misha

P.S.
Special thanks to Alexander Stankevich and Dima Razbornov (iRangers’ Sr. Solutions Architects), who were actively involved in crafting this blog post!

Written by Misha Hanin

Trusted Business & Technology Advisor, Solutions Managing Director & Senior Solutions Architect at iRangers International Inc. with more than 25 years of experience in the field of information technology, infrastructure analysis and design, implementing innovative and leading technologies for International companies around the globe in public and private sectors.

Over the years I was able to develop very strong technical and engineering skills which helped me to earn trusted advisor status with our clients. As one of the nearly 500 trained Microsoft Certified Masters (MCM) in The World (during 10 years existence of MCM program, just about 500 people in The World participated in this very intensive training), I have a winning track record in building and bringing projects to operational and measurable success.

I am honored to have been awarded Microsoft Most Valuable Professional (MVP). This award is given to "exceptional, independent community leaders who share their passion, technical expertise, and real-world knowledge of Microsoft products with others."