Fix Outlook Error “Cannot Send This Item” when Replying

Nowadays, email has established itself as the base of our daily interactions, both in our personal and professional lives. Yet, even the most dependable tools occasionally hit obstructions. Outlook users may have experienced the enigmatic and often vexing error message: “Cannot Send This Item.” In this blog post, we delve into the complexities of this error, dissecting its origins and equipping you with the knowledge needed to conquer it effectively.

When you see the message “Operation Failed in Outlook when Sending Email” in Outlook, there is an issue preventing the email from being sent. When you’re dealing with really long website addresses, like those with more than 2084 characters, there’s a problem. Sometimes, using a security feature called ‘Safe Links’ in Outlook can make these long web addresses longer. And when they become too long, Outlook can’t handle them properly, and they end up getting cut off or shortened.

You May Also Read: Send Large Files through Outlook

Common Causes of the Problem

• Large Attachments: One of the most common reasons for this error is trying to send an email with an attachment that exceeds the size limits imposed by your email provider or your organization’s email policies.
• Corrupted Email: Sometimes, the email itself may be corrupted or contain problematic elements, such as unsupported characters or damaged formatting.
• Outlook Profile Issues: A corrupted Outlook profile or misconfigured settings can also lead to this error.
• Outlook Add-Ins: Third-party add-ins or plugins can sometimes interfere with Outlook’s functionality and cause email-sending issues.

Also Read: Outlook is Sending Multiple Copies of an Email

Solve Outlook Cannot Send This Item when Forwarding Error.

The above section has gone through the common reasons for causing this error. Now, this segment will discuss the troubleshooting ways to resolve it.

#1. Change How Your Email Looks

To fix this error, you can make your email look different.

• First, open the email you want to work with.
• If you’re reading it in a small window, make it bigger by clicking on ‘Reply,’ ‘Reply All,’ or ‘Forward.’
• At last, click the ‘Format Text’ option inside the bigger window and then choose ‘Rich Text.’

NOTE:

HTML: This is how emails usually look in Outlook. It’s like making your email look fancy, like an appropriate document with all the fonts and colors.

Plain Text: This format works for all email programs, but this is plain and simple. You can’t make text bold or colorful and put pictures inside the email. You can only send images as separate files.

Rich Text: This is a unique format from Microsoft, and it only works with Outlook and some Microsoft programs. With Rich Text, you can do more, like using bullets, aligning text, and adding links. If you send something with Rich Text, any attachments look like little icons inside the email.

#2. Use the Web Version of Outlook

Sometimes, this problem only happens on the computer. So, if you’re having trouble, you can use the Outlook application on the internet instead.

#3. Remove Really Long Links

If you don’t want to do any other stuff, you can take out the super-long links. But be careful because those links might be necessary.

#4. Check Attachment Size

Ensure that the size of your attachments doesn’t exceed the limits set by your email provider. You may need to compress large files or use cloud-sharing services for big pictures.

#5. Disable Add-Ins

Temporarily turn off any third-party add-ins in Outlook and try sending the email again. If it goes through, you can re-enable the add-ins one by one to identify the problematic ones.

#6. Update Outlook

Ensure that you’re using the latest version of Microsoft Outlook. Sometimes, updating the software can resolve known issues.

NOTE: If you’ve corrupted Outlook PST files, opt for the Cigati PST Repair Tool. It will recover corruption from your targeted PST files without facing problems.

Sum Up!

The “Cannot Send This Item” error in the Outlook application can be frustrating, but it’s usually solvable with some troubleshooting. By following the steps outlined in this blog post, you can identify the root cause of the issue and take the appropriate actions to resolve it. Remember to keep your Outlook and system updated to minimize the chances of encountering such errors in the future. Email is a critical communication tool, and with a little patience and know-how, you can keep it running smoothly.

You May Also Read: The Attempted Operation Failed

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