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Automatic replies (Out of office assistant) versus Automatic reply using mailbox rule – Exchange Online |Part 1#7

In the current article series, we will review the different options for implementing Automatic Reply in Office 365 (Exchange Online) based environment.
Corresponding terms are Automatic respond, Autoresponder, Automatic replies or, Out of office.

The term “Automatic reply” (and of the equivalent terms) defines a configuration in which we configure a specific mail user (mailbox) to respond to incoming E-mail using a predefined text or E-mail template.

Automatic replies (Out of office assistant) versus Automatic responder using inbox rule.

Generally speaking, in Exchange based environment, there are two ways of implementing the
“Automatic reply” mechanism-

Automatic replies (Out of office assistant)

Describe an Exchange mailbox feature, that was created for scenarios, in which Exchange recipient is absent for a limited period of time (vacation, sick leave, pregnancy leave and so on).

The purpose of the Automatic replies is to configure the user mailbox to respond with a predefined E-mail template to each incoming E-mail so the sender will be aware of the “absence” of the specific Exchange user.

In former Exchange server versions, this feature was described as – Out of office. The current formal term is Automatic replies

Automatic reply using Exchange Inbox rule

The Exchange Inbox rule is implemented by a very sophisticated “rule engine” that enables Exchange user to create a “rule” which consist of a “condition”, “actions” and “exceptions”. The Exchange Inbox rule can be used for various business scenarios and one of this scenario can be described as “Automatic reply”.

Generally speaking, there are a lot of shared similarities between this Exchange option but despite the similarities, there is variance between this option such as – different management interfaces, different characters and so on.

Automatic responder using Automatic Replies (Out of office assistant) | Advantages and disadvantages

Automatic Replies (Out of office assistant) – Advantages

The main advantages of the “Automatic Replies” feature is as follows:

1.  Easy to use

The “Automatic Replies” is a very easy to configure option, without the need of using a sophisticated rule wizard.

2.  Setting a trigger for activation based on specific types of a recipient (internal recipient versus external recipient).

The “Automatic Replies” can be activated based on the following triggers:

  • There is an option to configure a different set of “Automatic Replies” in case that the sender is an originating user, versus a scenario in which the sender is an external recipient. The ability to differentiate between an internal organization recipient versus
    “non-organization recipient” enable us to use different sets of “response” for each type or recipient.

3.  Prevent “reply back loops” – Automatic Replies (Out of office assistant)

The outstanding advantage of the “Automatic Replies” mechanism is – that he can prevent “reply back loop”. The “Automatic Replies” mechanism, record the information about the E-mail reply that is sent as an automatic response to a specific sender.
In case that the automatic response was sent to a specific sender, and the same sender sends E-mail again, the “Automatic Replies” mechanism will not send again the automatic reply.

The Out of Office Assistant sends an automatic reply to notify users who send you messages that you are away from the office. Your reply is only sent once to a message sender. The count is reset when you toggle the Out of Office Assistant. Microsoft Exchange clears its internal “sent to” list when you disable the Out of Office Assistant.

If you would like to have a reply sent for every message, use Rules instead of the Out of Office Assistant.

[Source of information – Only one reply is sent to each sender when the Out of Office Assistant is enabled]

4.  Using the option of Mail tips

When organization Exchange recipient creates a new E-mail and adds the E-mail address of other Exchange recipients that configure the option of “Automatic Replies”, Exchange will generate a mail tips, and inform the sender about the fact that he is going to send E-mail to the destination recipient who is not available at the current time.

5.  Using inbox rule with a combination of Automatic Replies

There is an option to use a combination of Automatic Replies + inbox rule. This “combination” enables us to define more complex scenarios in which we want to “expand” the operations of the automatic response. For example, create a custom notification for a specific sender.

6.  Managing Automatic Replies using PowerShell

Exchange administrator can manage the “Automatic Replies” option using PowerShell. Using PowerShell enables us to implement bulk operations. For example – “activate” the Automatic Replies option for all organized users before a national holiday.

Automatic Replies” (Out of office assistant) | Disadvantages

The disadvantages of the “Automatic Replies” feature are as follows:

1 . Limited text and image design options.

  • The automatic response text that we can use is some We can add a text message that will be configured as “automatic response” but we cannot use a more advanced automatic response text that includes images and so on.
  • The “logic” of the “Automatic Replies” is restricted to a specific date range or, to the external recipient versus internal recipient. By default, the “Automatic Replies” doesn’t include a sophisticated “rule engine”, that enable us to create a rule that is “tailored” to a specific Business requirement.

Automatic respond using Exchange inbox rule | Advantages and disadvantages.

The alternative or the “competitor” of the Exchange Automatic is – the option of creating “Automatic respond” using inbox rule.

The feature of inbox rule is a well-known Exchange feature because the inbox rule is a powerful and useful tool that enables Exchange user to create a custom rule for a specific business need.

The Exchange “inbox rule engine”, can cover a very wide area of possible scenarios.

One of the possible inbox rules that we can create described as “have server reply using a specific message“.

Using this specific inbox rule option, enable us to create a custom response (E-mail template) that will be “executed” or “activated” when a specific condition is fulfilled.

For example, we can define a very simple condition that activates the “Automatic respond” each time that E-mail reaches to the recipient mailbox. Versus this “simple condition,” the inbox rule engine enables us to define a very sophisticated condition which is built from many parts.

Service mailbox, inbox rule and custom response

Most of the time, we will use the option of Exchange inbox rule that is configured to generate “Automatic Reply” by using a dedicated Exchange mailbox that will be configured as “service mailbox”.

The term “service mailbox” is for a formal technical Exchange term. I use this term for describing a mailbox (or other types of an Exchange recipient mailboxes such as Public Folder) that serve for representing a specific organization department such as – the Help Desk, Human Resource and so on.

Most of the time, the “service mailbox” is not implemented as a standard user mailbox that “belong” to a specific user, but instead, implemented as a Shared mailbox or Mail enabled Public Folder.

The relevant organization users who need access to the specific “service mailbox”, will be assigned with the required permissions such as Full Access permissions, Send As permissions, and so on.

Automatic respond using inbox rule | Advantages

  1. Inbox rule a powerful rule engine

As mentioned, the Exchange inbox rule evolved to become a very sophisticated rule engine, that can cover most of the common business scenarios. For example, we can create a very complex condition that will activate the Automatic response (“have server reply using a specific message“) only in a very specific scenario.

Another example is the ability to create multiple inbox rules, that will respond with a different template for different scenarios.

Automatic respond using inbox rule | Disadvantages.

1.  No History transaction records (partial support in loop back scenarios).

The main disadvantages of using an Exchange inbox rule as a tool for implementing Automatic respond is – that the inbox rule is not aware of “former Automatic respond” that was sent to recipients.

For example, in a scenario in which we create an inbox rule that will respond with a predefined mail template each time that someone sends E-mail to the recipient, the “respond” will occur every time, even in the case that the “source sender” sends E-mail repeatedly.

Versus the Exchange “Automatic Replies” (Out of office assistant) feature that includes a record for “respond E-mail” to a specific recipient, the inbox rule doesn’t include this information.

This disadvantage can lead to a scenario described as “mail storm” or “mail loopback”.

To understand better, the possible scenario of “mail loopback”, let’s use the following scenario:

  1. Recipient A mailbox was configured using inbox rule the respond with a specific E-mail template to each E-mail that is sent to recipient A.
  2. The recipient B mailbox was configured using inbox rule the respond with a specific E-mail template to each E-mail that is sent to recipient B.
  3. Recipient A sends E-mail to recipient B.
    The Inbox Rule of recipient B is “activated,” and recipient B responds by sending a reply to recipient A.
  4. The Inbox Rule of recipient A is “activated,” and recipient A respond by sending a reply to recipient B.

In this type of scenario, the mail flow between these two mailboxes (recipient A mailbox and recipient B mailbox) can continue forever!

When we use an inbox rule there is no way for predicting such a scenario or identifying such a scenario.

The scenario of “mail storm” or “mail loop back”” is not a common scenario because, in Exchange based environment, the Exchange server is “Smart enough” to add information to the E-mail header of the E-mail that was generated by the inbox rule as an Automatic reply.

This information should prevent “mail storm” scenario.

We will cover this issue in more details in the article – Automatic Reply in Office 365 -Dealing with mail loop (mail storm) scenarios |Part 7#7  

2.  Manage inbox rule using PowerShell

The Exchange administrator can manage the ” inbox rule” option using PowerShell, but the task of creating the specific condition, and the specific response is not so easy.

3.  Shared mailbox and Automatic respond using inbox rule

In case that we use Shared Mailbox as a “serviced mailbox” and we want to create an Automatic respond using inbox rule, we will need to use a little trick to be able to login to the Shared mailbox using Outlook mail profile, for creating the required Automatic respond using inbox rule.

We will review the required steps in the article – Setting up an Automatic Reply in Office 365 using Public Folder | Part 3#7

Automatic responder using inbox rule versus Automatic Replies (Out of office assistant) – Exchange recipient

In the next articles, we will review how to implement the option of ” Automatic respond” using Inbox rule and Automatic Replies (Out of office assistant) using three types of Exchange server mailboxes:

  • User mailbox
  • Shared mailbox
  • Public Folder

Each of this option has advantages and disadvantages.
For example-

  • Using Shared mailbox or Public Folder – in an Office 365 based environment (Exchange Online), we don’t have to purchase a license for Shared mailbox and for Public Folder.
  • Using the option of Public Folder enables us to easily share information between many users without the need of adding an additional mailbox to their Outlook mail profile

In the following table, we can see the matrix of specific Exchange recipient mailbox, and the support option in the two Automatic respond option.

The main conclusion is that the option of Inbox rule is supported when using all the Exchange recipient types.

The Exchange Public Folder doesn’t support the option of Automatic Replies (Out of office assistant).

Exchange rule and Automatic respond solutions. 

Q1: What about the option of using Exchange rule for implementing a solution of Automatic respond?

A1: The Exchange server rule infrastructure, consider as a very powerful and sophisticated “rule engine”.

The interesting thing regarding the “Exchange server rule feature” is, that although Exchange rule includes a huge amount of different options and business scenario, in the current time, there is no option to create an Exchange rule that will “activate” automatic response that will be sent to the sender (the mail originator).

In other words, in the current time, we cannot use the “Exchange server side rule” option for creating an “organization level” Automatic reply rule.

Implementing Automatic responder in Exchange on-Premises versus Exchange Online environment

The demonstrations in the current article series, are based on Office 365 and Exchange Online environment. It’s important to emphasize that most of the information is relevant to Exchange on-Premises base environment.

The o365info Team

The o365info Team

This article was written by our team of experienced IT architects, consultants, and engineers.

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