Can't drag and drop attachments between accounts, folders and out of Outlook into browsers.

Question

Can't drag and drop attachments between accounts, folders and out of Outlook into browsers.

Niv K 20

Hi,

Three days ago I stopped being able to drag and drop attachments and emails from Outlook.

This includes:

Dragging attachments into a new email from the same account or different account (only Copying and Pasting attachments to a new email works without having to save the attachment and attach manually).
Dragging attachments into a folder on the computer
Dragging any attachment - Regardless of file type - into a browser to upload files. I usually work with PDF Files and have had no problems until three days ago.
Dragging an email to another folder within the same account.

I have searched on the forum and found answers relate to this issue only occurring with the New Outlook. I can confirm I am still only using Classic Outlook and have also tried clearing the cache as recommended previously.

Please advise when this will be fixed, as it has a significant impact on workplace efficiency. Saving the attachment to a folder and then uploading, or dragging from the folder to a browser adds extra, unnecessary steps.

The image attached below shows what happens when I try to drag the attachment. This is just inside the email, and the circle with diagonal line through it stays when attempting to drag anywhere.

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Answer 1

Jade Ng 15,480 Microsoft External Staff Moderator

Dear @Niv K,

Thank you for providing the detailed description of the issue. I understand how disruptive this is, especially when drag-and-drop is part of your daily workflow.

Since you have confirmed that you are using Classic Outlook and that drag-and-drop was working normally until three days ago, this behavior is not expected. Drag-and-drop actions such as moving emails between folders, dragging attachments to File Explorer, attaching files to new messages, and dropping files into browser upload windows should continue to work in Classic Outlook.

To better isolate the cause, could you please confirm the following?

Does the issue affect all Outlook profiles/accounts or only a specific mailbox?
What version of Outlook are you using? (File > Office Account > About Outlook)
Are you running Outlook with administrator privileges?
Does the issue persist after completely closing and reopening Outlook?
Are you using Windows 11 version 24H2, and have any Windows or Office updates been installed recently?

As initial troubleshooting, please try:

1.Disable the Outlook setting “Optimize for compatibility”:

Select the File tab, then select Options.
On the General tab, under User interface options, select the option Optimize for best appearance.

Untitled

2.If you use an Exchange account, try temporarily toggling Cached Exchange Mode and test again. Turn on Cached Exchange Mode

3.Repair Outlook

Close Outlook and all Office apps.
Open Setting > App > Installed apps
Find Outlook for Window and right-click on it and select Advanced option.
Choose Repair Option.
Restart your computer after the repair is complete.

4.Create a new Outlook profile and test whether the behavior persists. Create an Outlook profile

There was a previously identified Microsoft issue that prevented drag-and-drop operations in Classic Outlook on certain Windows 11 24H2 systems after specific Windows updates. Microsoft later released a fix through subsequent Windows updates. For more detail, please refer to: Unable to drag and drop emails to folders in classic Outlook

If the issue persists after trying the steps above, please let me know, and I'll be happy to help you further.

I appreciate your cooperation and look forward to your update.

Jade Ng 15,480 Reputation points Microsoft External Staff Moderator

2026-08-03T00:30:43.8266667+00:00

Dear @Niv K,

I hope this message finds you well!

I just wanted to check in and see if you have any updates or additional information you’d like to share regarding your situation. If there's anything new or if you need further assistance, please don’t hesitate to let me know.

Looking forward to your response!
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Niv K 20 Reputation points

2026-08-03T23:23:17.56+00:00

Hi Jade,

Apologies for the delayed reply. I already had the optimize for best appearance selected, and already tried option 2 prior to reaching out.

Option 3 is what worked. Thank you!
Jade Ng 15,480 Reputation points Microsoft External Staff Moderator

2026-08-04T00:14:13.8033333+00:00

Dear @Niv K,

I am delighted to hear that your issue has been successfully resolved, and I am pleased to have been able to assist you. Should you encounter any further concerns, please do not hesitate to reach out to me, or feel free to create a new post so that other moderators can provide support.

Thank you very much for your valuable time and your cooperation.
Hiền Nhân 20 Reputation points

2026-08-07T03:20:47.1833333+00:00

Hi @Niv K,

I have a question about the following scenario: I have two Outlook on the Web sessions open in two separate Microsoft Edge windows (Window A and Window B).

Is it possible to drag and drop an email from Outlook in Window A directly into the compose box of Outlook in Window B?

I am asking because a user believes they were able to do this previously, but it is no longer working for them now.

Thank you!
Hornblower409 14,955 Reputation points

2026-08-08T13:56:07.9333333+00:00

@Hiền Nhân said

I have a question about the following scenario: ...

You will probably not get any help for your issue by adding to an existing post. I would suggest that you start a new thread using the "Ask a question" button at the top of this page to create a new Question and include the details for *your specific problem.*This provides much higher visibility to your issue than adding on to an existing post, which is only seen by people who are already following this question.