Unable to drag emails as an attachment to a new calendar invite item as an attachment (New Outlook)

Question

Unable to drag emails as an attachment to a new calendar invite item as an attachment (New Outlook)

Matthew To 20

Recently one of our colleagues reported an issue where she was unable to drag and drop emails from new outlook to a calendar invite as an attachment.

She was previously able to do so and has only found this to be an issue about a week ago. I've also tested this myself and have faced the same issue.
Is this a result of a recent update?

Lia V 8,115 Reputation points Microsoft External Staff Moderator

2026-07-24T15:21:28.8566667+00:00

Hi Matthew,

I am following up on the support thread that has been discussed and wanted to check whether you need any further assistance from my side.

If you have additional questions, please feel free to reach out at any time. I would be happy to assist further as needed.

Thank you again for your collaboration throughout the troubleshooting process.
Abe Botha 0 Reputation points

2026-08-13T01:39:35.82+00:00
I was able to perform some additional testing and identified a reproducible scenario that may help narrow down the cause.

In both New Outlook and Outlook on the Web, email drag-and-drop functionality works when a meeting is created from the primary Outlook window. I was also able to drag an email directly onto the Calendar icon to create a new calendar item successfully.

Reproduction Steps

Working Scenario

Open New Outlook.

Create a new Event/Meeting from the primary Outlook window.

Drag an email from the Inbox into the meeting.

The email is successfully attached.

Failing Scenario

Open New Outlook.

Right-click the Calendar icon and select Open in a new window.

Create a new Event/Meeting from the newly opened Calendar window.

Return to the main Outlook window.

Attempt to drag an email from the Inbox into the meeting.

The email cannot be attached.

I was able to reproduce this behaviour consistently, and the same result was observed in Outlook on the Web when using a separately opened Calendar window.

Based on testing, the issue appears specifically related to meetings created from a Calendar instance opened via "Open in a new window", rather than the user's mailbox, permissions, or the email message itself.

Workaround

Create the meeting directly from the primary Outlook window. In this scenario, drag-and-drop email attachments continue to function as expected.

Question

Can Microsoft confirm whether this behaviour is:

By design, where Calendar windows opened via "Open in a new window" are intentionally isolated from the primary Outlook session; or

A defect/bug, given that the behaviour is reproducible in both New Outlook and Outlook on the Web?

Any clarification on whether this is an expected limitation or a known issue would be appreciated.

I was able to perform some additional testing and identified a reproducible scenario that may help narrow down the cause.

In both New Outlook and Outlook on the Web, email drag-and-drop functionality works when a meeting is created from the primary Outlook window. I was also able to drag an email directly onto the Calendar icon to create a new calendar item successfully.

Reproduction Steps

Working Scenario

Open New Outlook.

Create a new Event/Meeting from the primary Outlook window.

Drag an email from the Inbox into the meeting.

The email is successfully attached.

Failing Scenario

Open New Outlook.

Right-click the Calendar icon and select Open in a new window.

Create a new Event/Meeting from the newly opened Calendar window.

Return to the main Outlook window.

Attempt to drag an email from the Inbox into the meeting.

The email cannot be attached.

I was able to reproduce this behaviour consistently, and the same result was observed in Outlook on the Web when using a separately opened Calendar window.

Based on testing, the issue appears specifically related to meetings created from a Calendar instance opened via "Open in a new window", rather than the user's mailbox, permissions, or the email message itself.

Workaround

Create the meeting directly from the primary Outlook window. In this scenario, drag-and-drop email attachments continue to function as expected.

Question

Can Microsoft confirm whether this behaviour is:

By design, where Calendar windows opened via "Open in a new window" are intentionally isolated from the primary Outlook session; or

A defect/bug, given that the behaviour is reproducible in both New Outlook and Outlook on the Web?

Any clarification on whether this is an expected limitation or a known issue would be appreciated.

Answer accepted by question author

0 additional answers

Your answer

Lia V 8,115 Reputation points Microsoft External Staff Moderator

2026-07-24T15:21:28.8566667+00:00

Hi Matthew,

I am following up on the support thread that has been discussed and wanted to check whether you need any further assistance from my side.

If you have additional questions, please feel free to reach out at any time. I would be happy to assist further as needed.

Thank you again for your collaboration throughout the troubleshooting process.

Answer 1

Hi Matthew,

Good day, and thank you for the clear description of the issue.

From my research, this does not appear to be the result of a recent product change. According to Microsoft's official article, Add pictures or attach files to emails in Outlook | Microsoft Support, dragging and dropping an email into a new email message or calendar event remains a supported feature in New Outlook.

In addition, I tested this behavior on my end and was still able to drag and drop an email into a calendar event successfully. Based on that, the behavior you are seeing may be related to a specific user, Outlook client, or environment rather than a general removal of the feature.

With that in mind, you may wish to try the following:

1/ Determine whether the issue affects all users or only specific users

This can help identify whether the problem is environment-specific or more widespread within your organization. If only one or a small number of users are affected while others can still perform the action successfully, that may point to a client-side issue, an account-specific issue, or a configuration difference.

2/ Test the same workflow in Outlook on the web

This can help determine whether the issue is specific to the New Outlook desktop client.

Create a new calendar event.
Select Open in new window.

User's image

Arrange the browser windows so that both the message list and calendar event are visible.
Select the email you want to attach.
Drag the email from the message list into the calendar event.

3/ Try dragging the email directly onto the Calendar icon

I have found that dragging an email directly onto the Calendar icon creates a calendar item from the email content. While this is not exactly the same workflow, it may help determine whether drag-and-drop functionality itself is working normally in Outlook.

User's image

4/ Contact your Microsoft 365 administrator

If the issue persists, as this is a supported feature that should normally work in New Outlook, this may indicate an issue that requires further investigation on Microsoft's side. Because of this, the best next step would be to have your IT administrator open a support ticket with Microsoft via the admin center. A technical support engineer can then initiate a remote session, review backend settings, and run diagnostics. If needed, they can escalate the case to specialized engineering teams who are well-equipped to perform advanced troubleshooting and provide targeted solutions.

As moderators, our primary goal is to provide helpful guidance and support through general troubleshooting steps. While we don’t have access to internal systems or administrative tools required to resolve account-specific or backend issues, we truly appreciate your understanding of these limitations. We genuinely hope the information we share helps point you in the right direction, and we're always here to assist as much as we can within our scope.

For guidance on how to request support in the admin center, please share this with you admin: Get support - Microsoft 365 admin. 

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I hope the information helps guide you to the next steps. Please feel free to share any additional details if you need further assistance.

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