Pro Introduction

In your Vacation and holidays, you shall not think about your work and for sure not look into your emails! So, here is the perfect guide to set up outlook in the best way to send outlook automatic reply like PRO when you are Out of the office.

Use Outlook Web and Not the normal Outlook

Here comes the PRO tip, because you probably use only the Outlook software for desktop like windows or mac. Now, the surprise is to use Outlook Web to set up the “outlook automatic reply” because more configuration is possible in Outlook Web then Outlook desktop app!

Do I have access to Outlook Live (web) ?

Everybody can access the Outlook web if a valid Microsoft Account with an Outlook license or office 365 package. (This means if you use Outlook desktop app you can simple login to Outlook Web).

Login to Outlook web and Not the normal Outlook

Login to Outlook Live Web, therefore use your Microsoft Username and password, what you also use in your outlook desktop app:

Go to https://outlook.live.com/owa/
Sign in with your Microsoft Username and password
If it gives you a selection of “Work” or “Private” account, then probably you must use the “Work” Account (see screenshot)

Open the advanced settings

After the successful login to Outlook Live, then navigate to the advanced settings:

Click on the right top corner on the (Configuration symbol)
On the right side, a new pane appears. Here go at the bottom and click “View all Outlook settings” (see screenshot)

Activate the normal Outlook Automatic Reply

In the advanced settings, you can configure in Outlook live many things:

Activate the automatic replies by checking the “Automatic replies on”
The time span when this setting is active, “Send replies only during a time period”. I strongly recommend this because then you cannot forget to activate/disable it.
1. In “Start time” I recommend inserting the last day in your office BUT set the hour to the exact time when you turn OFF your computer. This ensures that if you receive an email in the same day after working hours, then the automatic reply is already activated!
2. In “End time” I recommend inserting the first day in your office BUT set the hour to the exact time when you turn ON your computer. This ensures that if you receive an email in the same day before working hours, then the automatic reply is already activated!

Go PRO for the Outlook Automatic Reply

Now, I show you the settings available only in the Outlook live. They have some real advances at work, specially if you have a lot of meetings:

You can block your Outlook calendar for this time period. This ensures your work colleagues see in the schedule assistant that you are Out Of the office, they will be thankful if you use this feature!
“Automatically decline new invitations” is a must-have to activate to respond to meeting invitations, so all participants can see your decline in the meeting overview.
“Decline and cancel my meetings” helps you to bulk cancel all your meetings where you are the organizer.
1. As default, all meetings in the given time period are selected to cancel. You can manually unselect some if you don’t want them to get cancelled.
2. Important: The meetings are only canceled if you click “Save”!

Save your settings and start your Vacation

To complete the configuration, set the last settings:

Set the email message for the Outlook Automatic Reply.
1. Optionally, you can set a different email message for contacts outside and inside your organization.
Anyhow, now it’s time to click “Save”.
1. After saving, Outlook will start to cancel all your meetings in the time period if specified, this could take some minutes.
2. Now, you are done. You don’t need to worry more about activating it, as soon as the “Start Date” comes the automatic replies are sent.
Go out of the office, you deserve it!

Alternative: Outlook Desktop app to Set-up auto-reply (out of office)

If for some reason you cannot use the Outlook live to configure it, then I recommend to check out this 40 seconds video by Microsoft to see how to set-up the outlook automatic reply on Windows and Mac for the desktop version:

Written documentation can be found here on how to set up the automatic reply on Outlook desktop app.

OOTO for Microsoft Teams and GitHub

I highly recommend setting up for other applications and also the Out Of The office feature. Almost every software with communication offers somewhat of an “automatic reply” feature:

Microsoft Teams: Make sure to set an out-of-office status in Teams, find the Microsoft documentation here.
GitHub: Change your Profile status to “busy” so other users get notified about your vacation, find the Github documentation here.

Do you need help for Outlook?

I am a software engineer with over 8 years of professional development experience in desktop applications. So, you are in the right place to ask questions:

I do VBA Macros for Outlook, but also Excel and Word.
I create VSTO Addins for Outlook, Excel, PowerPoint and Word to automate your monotone work process and save you time.
- Example 1: Excel, prevent PDF publishing if certain criteria in the Excel file are not filled.
- Example 2. Outlook, force users to classify the email before sending them.
- Example 3: Excel, match source files like PDFs with excel rows and sync data.
For any question, contact me now, and I always find a solution!
- patrick@limitlesspatrick.com
- On Fiverr @Patrick_iTech