The attempted operation failed – Outlook Attachment error

Outlook is an integral part of Microsoft Office and provides a plethora of utilities and services. Its most popular service is webmail, but it also offers contacts management and calendaring’s users have reported an error that says ‘The attempted operation failed’ while attaching a media file to an outgoing email. If you’re one of those people, this article is for you.

Outlook Attachment error – The attempted operation failed

Related Article: Outlook Web App cannot download attachments

If attaching a file to your email results in Outlook displaying an error message reading “The attempted operation failed,” try one of these fixes:

  • Update Outlook
  • Run Outlook in Normal (non-compatibility) mode
  • Disable AutoSave on Outlook
  • Open Outlook in Safe Mode
  • Change the text format of your e-mail
  • Repair the Microsoft Office Suite
  • Enable Cached Exchange Mode

Update Outlook

It’s always a good idea to make sure you’re running the latest version of Outlook before making any changes. Microsoft releases Outlook updates quite frequently, and the bug you’re facing might have been fixed in one of them.

You can check for updates by clicking on Files on the top-left corner of the screen > Office Account > Update Options. Once updated, restart to check if the issue has been resolved.

Run Outlook in Normal (non-compatibility) mode

Here’s how you disable the compatibility mode if Outlook is running on your PC under that.

  • Click on the App icon from your desktop and select Properties
  • From the tabs on top, click on Compatibility
  • In the Compatibility box, un-check the Run this program as administrator box and apply these settings.

The changes have been saved and Outlook will now open in Normal mode.

Disable AutoSave on Outlook

  • Open Outlook and click on File
  • Then, select Options from the left-pane menu.
  • Click on the Mail tab and scroll down to ‘Automatically Save Items that have not been sent after:’. Uncheck this box and save these settings.

Open Outlook in Safe Mode

Outlook has a built-in Safe Mode that helps it run without preinstalled add-ins used to automate tasks. These add-ins may be at fault here, so if you try running Outlook without them, you may just be able to rid yourself of this problem.

Close Outlook on your PC and open the Run dialog box by pressing the Windows and ‘R’ key combination. In the space, copy and paste ‘Outlook.exe /safe.

If Outlook is working fine in safe mode, it means one of our add-ins is causing problems.

One by one, proceed to disable add-ins. To do so, click on File, then Options, and from the options tab on your left, select Add-ins.

The option to Manage add-ins is located at the bottom of the box, next to a drop-down. This drop-down list all active Outlook add-ins. To disable each add-in, select it one by one.

Once finished, try the process again to check if files are still not being attachments properly.

Change the text format of your e-mail

It’s possible that the issue lies in the format of the email. Try changing the format to HTML. The default format is HTML, so it’s possible your HTML permissions are not in line with file attachments.

Open the Outlook application and select the email from the drafts folder that you were having trouble with. From the top ribbon, click on the Format Text tab. This will give you the option to change the email’s text format.

Change it from HTML to rich text and save these settings. Close the draft and revert to HTML by following the same steps. This may help you solve the issue at hand.

Repair the Microsoft Office Suite

Try repairing the office suite if the above-mentioned fixes did not help.

Open the Run command and type ‘appwiz. couple’. If you’re not comfortable with it, this page can also be approached via the Control Panel.

Search for Microsoft Office or Outlook in your app store. From the maze of apps, look for Microsoft Office or Outlook. Right-click when found and select Change. Click on Quick Repair and further select Repair.

If Quick Repair doesn’t fix it for you, you might want to try Online Repair as well.

Enable Cached Exchange Mode

Lastly, you can try enabling the Cached Mode. Click on File and from the Account Settings drop-down, click on Account Settings.

Click on the e-mail ID you want to change. This will open the Exchange Account settings. Click on More Settings. A small dialog box will appear with three tabs on top. Click on Advanced. Check the Use Cached Mode box and save the settings.

Restart Outlook and check if the issue persists.

I hope one of these solutions will help you solve the problem so you can easily send emails from Outlook.

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