Fix Outlook The Operation Failed Attachment Error [2024]

Microsoft Outlook is a wonderful tool that millions of people utilize daily, and with each Microsoft update, it’s becoming more stable & feature-rich. However, like all programs, there will always be the occasional problems that just don’t go away.

Many businesses depend on Outlook to keep their operations running, and having it break unexpectedly can end up costing lots of money and frustration. Many users have reported getting The Operation Failed error as they try to open or send an important file in email.

Although there could be many reasons causing this error, there are a number of general troubleshooting steps that are pretty straightforward. Since I’ve faced this issue myself, I conducted a thorough research on this matter & shortlisted the most effective fixes for this error message.

So let’s get straight to the topic, shall we?

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What Triggers The Operation Failed Error on Microsoft Outlook?

The attempted operation failed. An object could not be found. error can occur due to various factors ranging from compatibility issues to internal conflicts with other applications.

Here are the reasons which can trigger this error message:

Older Outlook Client

Microsoft regularly updates Outlook to prevent security issues and improve compatibility and program features. If you are using an outdated version, you are most likely to face the attachment error message.

Conflicting Apps

Conflicting with other apps in your system, such as anti-virus,firewall etc, can cause this error when attempting to do a particular task.

Conflicting Add-ins

Even though third-party add-ins add greater functionality to Outlook, some add-ins might end up conflicting with Outlook’s basic functionality & cause The Operation Failed error.

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Running in Compatibility Mode

Some of the essential components in Outlook won’t be able to perform their intended operation if Outlook is running in compatibility mode, which will affect the overall performance & often show error messages on certain tasks.

Missing or Corrupted PST Files

Outlook needs access to the .pst files to store local copies of its various data. If for some reason, the PST files get missing or corrupted and hence inaccessible for the program, the user will face the failed error message.

Drafts Folder Permission Issue

The drafts folder saves messages that haven’t yet been completed or have to be sent later on. Due to a software glitch in Outlook, many users experience the attachment error message.

Corrupted or Improper Installation

If you’re facing Operation failed because of a registry or installation problem error, the Office/Outlook installation itself is incomplete or corrupted.

Duplicate Rules

Rules are automated Outlook actions that perform on sent or received email messages based on conditions you specify, such as moving all messages from a specific person into a folder other than your Inbox.

If they are set incorrectly or restrict the attachment feature, you will end up with the attachment error message.

Additionally, your system administrator might have some Outlook restrictions (if you are from an organization that puts the restriction manually), which might cause the attachment error on your end.

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How to Fix Microsoft Outlook Operation Failed Error

Let’s discuss the effective solutions for Microsoft Outlook’s The Operation Failed error based on the above-mentioned possible reasons.

Before we begin, make sure you have administrator access to the system. If you are on a corporate network, inform your organization’s I.T. administrator first.

Here are the solutions for Microsoft Outlook Operation Failed error:

1. Update Office/Outlook

Microsoft regularly updates Outlook to improve its stability, add new features and squash bugs in it. If the error in question is happening due to a bug & Microsoft has already patched the fix, updating your Outlook client will solve this issue.

Here are the steps to check for Office/Outlook updates:

Click File > Office Account.
Go to Update Options & select Update Now.
Restart Outlook & check if the problem has been solved.

If you’re already using the latest version of Outlook, ignore this step & move on to the next procedure.

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2. Turn off Compatibility Mode for Outlook

Compatibility mode allows older or incompatible software to remain compatible with the computer’s newer hardware or OS. If Outlook is running in compatibility mode, it might not be able to perform some of its features/add-ins & end up showing error messages.

In that case, you need to run Outlook in non-compatibility mode by turning off the compatibility option from its Properties settings.

Perform these steps to turn off compatibility mode for Outlook:

Press Windows Key+S & type exe.
Right-click on Outlook & select Open file location.
Right-click on OUTLOOK & hit Properties.
Go to the Compatibility tab & uncheck the Run this program in compatibility mode for:
Click Apply.

Now restart Outlook & check if it is functioning properly.

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3. Disable Add-ins

Sometimes two or more add-ins on Outlook can conflict with each other. In that case, users might get the attachment error when they try to open or send a file in an email.

Here’s how to disable add-ins one by one:

Open Outlook in normal mode.
Click on Files> Options> Add-ins.
Select your desired add-in that you want to disable from the Manage section & click Go.
Uncheck the add-in & restart Outlook.

If you don’t want to disable the add-ins, there’s a built-in safe mode in Outlook that runs the program without the add-ins. To run Outlook in safe mode, Press Windows Key+R & type outlook.exe /safe.

4. Disable Conflicting Apps

Internal softwares such as anti-virus or firewall can often conflict with the program as users try to perform certain tasks. This can lead to causing an error in Outlook if those softwares mistakenly flag the attachment as harmful.

Users can follow these measures to avoid this kind of inconvenience:

Set an exception for Outlook in your Windows Firewall.
Update your anti-virus.
Uninstall & reinstall anti-virus.
Disable anti-virus or Windows Firewall.

If the issue still persists, consider removing the anti-virus software completely from your PC or contact the support team of the anti-virus company.

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5. Reinstall Outlook

If you’re facing a registry or installation-related error when you’re trying to attach a file or open an email, it means the Office/Outlook installation itself is incomplete/corrupted.

Microsoft Office has a built-in repair tool for such cases, which lets users clear any issues relating to installation.

Here’s how to use the built-in repair tool in Microsoft Office:

Press Windows Key+S & type control panel.
Click Control Panel & select Programs> Programs & Features.
Select Office & click Change.
Click Yes if UAC prompts.
Hit Quick Repair & click Ok.
Click Repair> Continue.
Wait for completion & then restart your PC. Check if the problem has been resolved.
If the issue still persists, follow steps 1 to 4 & select Online Repair.
Select Repair> Continue.
Wait for the completion of the repair process, then restart your PC.
Start Outlook & check if the issue has been solved or not.

If the issue still hasn’t been resolved, continue to the next method.

6. Change Text Format in Email

Lots of users have reported that they’ve experienced the attachment error message when creating an email with HTML & save it to Drafts. This means that there are some permission related issues with the Drafts section for the HTML part of an email.

Users should change the email Format from HTML to Rich Text and then revert to HTML if they’re facing such a problem.

Here are the steps to change the text format in an email:

Open the problematic email in Outlook.
Navigate to the Format Text tab & change from HTML to Rich Text.
Save & close the email.
Reopen the email & go to the Format Text tab.
Change the format from Rich Text to HTML.

Now open the problematic email again in Outlook & check if you can add attachments. If not, move on to the next step.

7. Disable Auto Save

Some users have reported that when they open a saved message from the drafts folder & try to send/receive or attach a file to the email, they face the attachment error message. It happens due to a bug related to the Drafts folder.

Disabling the autosave feature restricts the message from going into the drafts folder so that the drafts folder bug doesn’t affect the email.

Here are the process to disable the auto-save feature in Outlook:

Open Outlook & select File.
Click Options> Mail.
Scroll down to the Save messages section & uncheck the Automatically Save Items that have not been sent after this many minutes box.

Now restart Outlook and check whether the program is operating as intended or not.

8. Create a New Outlook Profile

Microsoft Outlook saves your data & address book information in .pst files & needs access to the PST folder in order to function properly. This is either stored online or locally.

In case your Outlook profile or the PST file gets corrupted or missing, Outlook won’t be able to access files and folders containing your Outlook data. As a result, Outlook will show “Operation failed” attachment error.

Creating a new profile will automatically add a new .pst file to your profile & thus may solve the attachment error.

Here are the steps to create a new Outlook profile:

Press Windows Key+S & type control panel.
Select Control Panel & click Mail.
Click on Show Profiles from the Mail Setup – Outlook tab & hit Add.
Enter your desired title in the Create New Profile box & click Ok.
Enter the required email account details in the Add Account section.
Click Next & go through the rest of the setup wizard.
Press Windows Key+R & type Outlook.exe /safe.
Select the new profile from the drop-down list in Choose Profiles section.

For Windows 7/8/8.1 users, press Windows Key+S & type Mail. Then select the Mail program shown in the picture below. Afterward, follow the above-mentioned 3 to 8 steps accordingly.

9. Apply the Correct Configuration in Outlook

Microsoft Outlook lets you use multiple profiles in one application. If you have configured Exchange server account and Google apps sync for the Outlook account in one single profile, you might face the Operation Failed error.

You can solve this issue by creating multiple profiles where one profile is connected to the Exchange server, and another profile is configured with Google apps sync.

10. Repair PST File

Outlook uses the PST files to access the user’s data for the email & attachments when you try to send/receive an email. The PST files are stored locally or on a server if you’re using a corporate network.

If for some reason, the PST gets corrupted or missing, Outlook won’t function as intended & show the attachment error; hence the users become unable to send or receive emails in Outlook.

Fortunately, Microsoft has a built-in utility called Scanpst.exe which can check & repair corrupted .pst files and resolve the attachment error related issues.

Follow these steps to repair the Outlook data file (.pst) using Scanpst.exe:

Press Windows Key+S & type exe.
Right-click on Outlook & select Open file location.
Scroll down & find SCANPST.
Right-click on SCANPST & select Run as Administrator.
Hit Browse in Microsoft Outlook Inbox Repair.
Choose the default PST file. The default path for Outlook 2010 to 2019 is:

For Windows 10

C:\Users\%username%\Documents\Outlook Files

For Older Windows Versions

C:\Documents and Settings\<username>\Local Settings\Application Data\Microsoft\Outlook

Click Start.
Select Make a backup of scanned file before repairing option to create a backup copy if prompted.
Click Repair.

You can also use 3rd party software to repair & restore corrupted PST files. But using the built-in utility is the best method.

11. Clean Boot Windows or Run Windows in Safe Mode

Some 3rd party or built-in services can interfere with Outlook’s basic functionality & cause Operation Failed error when adding attachments to an email. Clean booting Windows can resolve this issue.

Here’s how to clean boot Windows:

Press Windows key+R & type msconfig.
Hit the Enter button.
Select the Selective startup section and choose Load system services and use original boot configuration.
Uncheck Load startup items box.
Go to Services tab and check the Hide Microsoft services box.
Hit Disable all.
Select Apply & click Ok.
Select Restart from the pop-up window.

Or, you can try running your Windows in safe mode.

Here’s how to run Windows in safe mode:

Right-click on the Windows icon.
Select Power(for Windows 10) / Shut down or sign out(for Windows 8/8.1). Then click on Restart while holding the Shift button on your keyboard.
Select Troubleshoot> Advanced options from the blue screen titled Choose an option.
Click Startup Settings, and then select Restart.
Press 5 once the screen comes back.

After your PC reboots, open Outlook & check if the problem has been solved or not.

12. Change Outlook Connection Mode

Outlook has two modes to connect with an Exchange server, Online Mode & Cached Mode. In Cached Mode, a copy of your mailbox is saved on your computer locally. This copy provides quick access to your Outlook user data and is frequently updated with the Exchange server.

If a server connection problem occurs while trying to connect with the Exchange server, Outlook might show the attachment error message. You should change the connection mode with the exchange in order to solve this matter.

Here are the necessary steps to change Outlook’s connection mode:

Open Outlook & click on File.
Click on Account Settings.
Select Account Settings again from the drop-down menu.
Select your account from the Email tab & click Change.
Click on More Settings in Exchange Account Settings.
Navigate to the Advanced tab.
Check the Use Cached Exchange Mode box if it was unchecked.
Uncheck the Use Cached Exchange Mode box if it was checked.
Restart Outlook & check if the issue has been resolved.

Also, make sure your internet connection is running properly when Outlook tries to establish a connection with the Exchange server to sync.

13. Delete Outlook Rules

In Microsoft Outlook, a Rule is an action that will be applied to sent or received email messages if they meet certain criteria.

If there are duplicate rules or rules that conflict with each other, Outlook might throw an error message when performing a specific task, such as adding attachments or sending/opening emails.

In that case, you’ll need to delete the conflicting rule from your Outlook profile.

Follow these steps to delete rules in Outlook:

Open Outlook & click on File.
Click Manage Rules & Alerts.
Select the rule that you want to delete.
Hit Delete.
Click Yes.
Click Ok.

Alternatively, you can delete all the rules in all email accounts in your Outlook app.

Here’s how you can delete all rules in every email account:

Exit Outlook.
Press Windows Key+R.
Type outlook.exe /cleanrules and hit the Enter button on your keyboard.

FAQs

Why does Outlook’s Operation Failed attachment error occur?

Outlook’s ‘Operation Failed’ Attachment error occurs for various reasons such as an older version of the Outlook being used, Outlook being run in Compatibility Mode or problems with other internal Outlook components like PST files.

Why is Outlook not uploading an attachment?

Outlook might not upload an attachment based on the settings in sharing preferences. You can change your Outlook’s sharing preferences by navigating to Mail > Attachments.

How do I delete an email that is stuck in my inbox?

To delete an email stuck in Outbox, Go to the Send/Receive tab and click Work Offline. After that, switch to Outbox, right-click the message and select Delete.

What is the ideal attachable file size limit for Outlook?

For Outlook or Gmail, the combined file size limit is 20MB, and for Exchange accounts (business email), the default combined file size limit is 10 MB. If a file exceeds this limit, your email provider might switch to their online drive solution(such as Google Drive) to store & share the large attachment files.

Closing Thoughts

The desktop version of Outlook is perhaps one of the world’s most popular email client apps. While it might be a well-made application with many great features, sooner or later users will experience some inconvenience.

When you least expect it, you might get stuck on The Operation Failed error, which prevents you from opening a file or sending an important email.

Hopefully, this write-up will fix this annoyance for you in no time. If you need any further assistance or have found another solution, let us know in the comment section below.