Office 365 Outlook - Opening Multiple Calendars Automatically at Start-up

Question

Office 365 Outlook - Opening Multiple Calendars Automatically at Start-up

BP 25

I have 2 professional calendars in Outlook.
Every day, when I open Outlook calendars, I have to select both in the menu and overlay them manually.

I would like Outlook to remember this setting and reopen my overlayed calendars by default at startup.

Currently, it only opens one of them (I guess the last one I clicked on before quitting).

What is the right method?

Best regards,

BP 25 Reputation points

2025-12-19T09:25:01.1+00:00

This has been a daily annoyance for 10 years, I wish a feature was developped!

Answer accepted by question author

Vergil-V 13,545 Microsoft External Staff Moderator

Hi @BP
Thank you very much for sharing your updates. They really helped me understand your situation better.

I followed the steps you described and observed the same behavior when opening a new window in Calendar. It defaults to the standard calendar view.

After further testing, I was able to successfully open a new calendar window that retains the last view choice. Here’s how I achieved this:

Step 1: Instead of going directly to the Calendar section to open a new window when first launching Classic Outlook, I opened a new window from the Mail section by selecting View > Open in New Window.

Step 2: Once the new window was open, I switched to the Calendar section. This time, the view reflected the previously saved settings.

The key observation is that if you navigate to the Calendar section first, even opening a new window from Mail afterward will still default to the single selected calendar. To achieve the desired outcome, avoid selecting the Calendar section before opening the new window.

I would truly appreciate it if you could test this on your end and let me know if you experience the same results.

If you do, I highly recommend sharing your feedback through Ideas · Community

This is the official channel for submitting suggestions, and it ensures that your feedback reaches Microsoft’s development team, where it can help shape future updates and improve the overall experience.

Your feedback is valuable and truly appreciated.

Once again, thank you for your time and contribution.

BP 25 Reputation points

2025-12-19T14:24:14.31+00:00

True!

When I left-click on the calendar icon on the left, then the calendar is displayed as expected (and then I can right click on the eMail icon > open in a new window)

If I right click>open in a new window on the calendar, I only see 1 calendar

Thank you for pointing out, a new era in my usage of Outlook is starting :)
Vergil-V 13,545 Reputation points Microsoft External Staff Moderator

2025-12-19T14:33:31.1933333+00:00

Hi @BP
Thank you for confirming.

I’m happy to hear that my insight was helpful.

If your question or concern has been addressed, please consider marking any helpful responses as “Accepted Answer”. Doing so helps others in the community find useful guidance more easily and keeps the conversation productive for everyone.

Thanks again for your time

2 additional answers

Your answer

BP 25 Reputation points

2025-12-19T09:25:01.1+00:00

This has been a daily annoyance for 10 years, I wish a feature was developped!
BP 25 Reputation points

2025-12-19T14:24:14.31+00:00

True!

When I left-click on the calendar icon on the left, then the calendar is displayed as expected (and then I can right click on the eMail icon > open in a new window)

If I right click>open in a new window on the calendar, I only see 1 calendar

Thank you for pointing out, a new era in my usage of Outlook is starting :)
Vergil-V 13,545 Reputation points Microsoft External Staff Moderator

2025-12-19T14:33:31.1933333+00:00

Hi @BP
Thank you for confirming.

I’m happy to hear that my insight was helpful.

If your question or concern has been addressed, please consider marking any helpful responses as “Accepted Answer”. Doing so helps others in the community find useful guidance more easily and keeps the conversation productive for everyone.

Thanks again for your time

Answer 1

Hi @BP

Thank you for contacting the Microsoft Q&A forum.

I understand your concern regarding Classic Outlook not saving the last Calendar view in your environment. I tested this behavior in my Classic Outlook (Microsoft 365 MSO, Version 2511 Build 16.0.19426.20186), and in my case, the feature worked as expected.

To better understand your situation, could you please clarify the following:

What is the current type of your account: IMAP, POP, or Exchange?
What version of Outlook are you using: Outlook 2016, 2019, 20xx, or Outlook for Microsoft 365?

For visual confirmation, would you be able to share a screenshot showing your Outlook build in a private message?

Please check your inbox for an email with the subject “New private message on Microsoft Q&A question” to review my response.

To check your Outlook build, please go to File> Office Account > About Outlook

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Additionally, I tested Outlook on the web, and it behaves consistently with Classic Outlook. The last view choice is saved after reopening.

If I’ve misunderstood any part of your situation, or if you have further questions or updates, please don’t hesitate to reply. I’m here to help.

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

BP 25 Reputation points

2025-12-19T12:34:12.78+00:00

Thank you for answering, Vergil.

To answer you questions:

My account is a MicroSoft Exchange account

My build is "Microsoft® Outlook® pour Microsoft 365 MSO (Version 2408 Build 16.0.17928.20730) 32 bits"
There might be a misunderstanding around the "feature worked as expected" statement. I do not know what was intended, but what I observe is:

I open the calendar in a new window (through the Windows app)

Under "my calendars", I select my 2 calendars (both associated with my account, one shared, one private)

I click on the "overlay" and get the view I want :)

I quit Outlook (usually at the end of the day, before turning the PC off)

When I reopen Outlook, only one window opens (the inbox)

I reopen the calendar in a new Window

Only one of the 2 calendars are displayed in the large view :( I have to return to step 2 above. (This is where I would expect the 2 calendars to be restored)

Answer 2

Outlook does not have a built-in feature to remember the overlay settings for multiple calendars upon startup. Each time you open Outlook, it typically restores the last selected calendar view, which may not include the overlay of multiple calendars.

To manage multiple calendars more effectively, you might consider using the following workaround:

Create a Group Calendar: If your organization allows it, you can create a group calendar that includes events from both calendars. This way, you can view all events in one place without needing to overlay them manually.
Use Calendar Sharing: If the calendars belong to different accounts, ensure that they are shared appropriately so that you can access them easily without needing to switch back and forth.

Unfortunately, without a specific setting to save the overlay state, you will need to manually select the calendars each time you start Outlook.

References:

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Office 365 Outlook - Opening Multiple Calendars Automatically at Start-up

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