Outlook Attachment error - The attempted operation failed

Outlook is one of the premium and most integral parts of the Microsoft Office suite. It provides a plethora of utilities and offers several services like webmail (its most popular service), contacts management, and calendering. The email services from Outlook are used extensively by people and several of them have reported an error that says ‘The attempted operation failed’ while attaching a media file to an outgoing email. If you are one of those people, this article is for you.

Outlook Attachment error – The attempted operation failed

If when you try to attach a file to your email, Outlook throws up an error message The attempted operation failed then one of these fixes is sure to help you:

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

1] Update Outlook

Before you get on to make changes on Outlook, it’s best to make sure that you’re running the newest version of the app and if not, then updating it. Microsoft rolls out Outlook updates quite frequently and the bug you’re facing might’ve 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.

2] 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 settings have now been applied so Outlook is running under Normal mode thereon out.

3] 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.

4] Open Outlook in Safe Mode

Outlook comes with 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 just fine in safe mode then it means one of our add-ins is giving your problems.

Proceed to disable the add-ins one by one and see. Click on File and further select Options to do so. From the options tab on your left, click on Add-ins.

At the bottom of the box is an option to Manage these add-ins, next to which is a drop-down. This drop-down lists all the active Outlook add-ins. Select each one by one and disable them.

Once done, retry the process and check if the files are attachments are still not going through properly.

5] Change the text format of your e-mail

The issue here may lie in the format of the e-mail, in which case you can try changing that. The default format is HTML, so maybe your HTML permissions are not in line with file attachments. Here’s how you can change it:

Open Outlook and from the drafts (since the e-mail didn’t go through), select the one in which you faced the issue. Now, from the tabs ribbon on top, click on Format Text. This will allow you to change the mail’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.

6] Repair the Microsoft Office Suite

If none of the above-mentioned fixes were of any help to you, it’s time you try Repairing the Office Suite as well.

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

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 the Online Repair as well.

7] 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.

Select the e-mail ID you are operating and click on Change. This will open the Exchange Account settings. Here, 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.