Sending Auto-Replies from Shared Mailboxes

Configure Shared Mailbox Auto Reply for External Contacts

Contact handling is an important part of website communication. Most sites have a contact form that people can fill in to ask questions, perhaps after passing a CAPTCHA test. Behind the scenes, the information from the form might end up in an email to allow the site owners to deal with the query, which is how things should work normally.

Much to the embarrassment of the Office 365 for IT Pros team, we discovered that the contact form for our website has not worked for quite a time. We’ve fixed the problem now to make sure that if anyone uses the contact form to ask a question about the book or comment on book text, the site emails the query to a shared mailbox. If anyone’s interested, we upgraded the site to use the WPForms Lite plug-in for WordPress.

Suitably chastened, we have reached out to people who entered queries through the contact form to follow up and make sure that their questions are answered.

Shared Mailboxes versus Microsoft 365 Groups

Now that everything is fixed on our web site, contact messages sent to Office 365 for IT Pros flow into a shared mailbox. We could use the Microsoft 365 group to process book comments, but it’s cleaner to separate the two. And anyway, we want to use an auto-reply message to acknowledge the receipt of queries, and that feature isn’t supported yet by Microsoft 365 groups (see this comparison between shared mailboxes and Microsoft 365 groups). Some people don’t know that shared mailboxes support auto-reply, but they do and it’s a very useful option at times. For instance, when national holidays roll around, you can use PowerShell to quickly configure shared mailboxes used for customer communication with an appropriate auto-reply message saying that responses will be delayed.

We do use a Microsoft 365 group to organize the production of the book because we keep our chapter and other files in a SharePoint Online site and use Teams to discuss different aspects of the book, like what we’re working on in a monthly update or who hasn’t filed their chapter updates for a monthly update. So many options exist within Microsoft 365 to achieve goals in different ways that it’s often hard to decide which is best. In our case, being able to send auto-replies for contact messages tipped the balance.

Configuring the Distribution List

The email address used for comments configured on our website directs messages to a distribution list. The membership of the distribution list includes the shared mailbox and some other user mailboxes that might be involved in answering queries.

Because the first address reached by inbound messages is a distribution list, we need to configure the list to allow the generation of auto-reply messages and to allow external people to send messages to the list:

Set-DistributionGroup -Identity O365.Book.Comments -RequireSenderAuthenticationEnabled $False -SendOofMessageToOriginatorEnabled $True

To configure the shared mailbox auto reply, we use the Set-MailboxAutoReplyConfiguration cmdlet:

$AutoReplyText = "<h1>Thanks For Your Message</h1><p>We've received your email to <b>Office 365 for IT Pros</b>. If we need to respond to you, we'll be in touch by email within 48 hours. If you need help faster, reply to this email and we'll accelerate our response.</p><p>Best Regards</p><p><i>The Office 365 for IT Pros team</i></p>"
Set-MailboxAutoReplyConfiguration -Identity book.comments@office365itpros.com -AutoReplyState "Enabled" -InternalMessage $AutoReplyText –ExternalMessage $AutoReplyText -ExternalAudience 'All' 

Figure 1 shows the auto-reply we generate:

The technique of allowing Exchange Online to generate and deliver auto-reply messages for messages received by mailboxes through their membership of a distribution list is uncommon but it is used in practice (which is why the SendOofMessageToOriginatorEnabled parameter exists). For instance, this recent example of a use case is in the Microsoft Technical Community.

Another thing to check is to ensure that the shared mailbox doesn’t have a forwarding SMTP address set (this article is worth checking out when debugging OOF issues). Exchange Online won’t send auto-replies for a mailbox when a forwarding address is set.

Forwarding from a Shared Mailbox

We could have reversed the process and configured the shared mailbox to forward messages to another address. Any valid internal SMTP address works including one for a distribution list, but the outbound spam filter probably blocks forwarding to external addresses. If the organization blocks forwarding to external addresses, senders receive a non-delivery notification (5.7.520 Access Denied). In general, mail forwarding from mailboxes is a practice to avoid, so it’s one that we decided not to investigate too much.

Normal Service Resumed

Running a website throws up challenges on an ongoing basis. We should have caught the problem with our contact form earlier and sincerely regret if this caused anyone any extra hassle. On the upside, it did give us a chance to review the handling of contact queries from the website through to Exchange Online to make sure that everything now works as it should.

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