How to Fix ‘Outlook Cannot Send This Item’ Error

Imagine you are working on an important project and you need to send an urgent email to your team. You compose the message, attach the necessary files, and press Send. But instead of the satisfying ‘Sent’ notification, you get the frustrating ‘Outlook cannot send this item‘ error message.

We all have faced this issue, but don’t worry, there are many solutions to this common problem

In this blog post, we will explore the reasons why you might encounter ‘Outlook cannot send this item’ error and provide you with easy-to-follow steps to fix it.

Whether it is a problem with your email attachments, your Outlook profile, or something else entirely, we have got you covered.

This guide is here to be your hero. We’ll break down the reasons why you might be seeing this error message. Additionally, we’ll walk you through some simple fixes to get your emails flying out of your inbox in no time.


How to fix Microsoft outlook cannot send this item?

Has the ‘Outlook cannot send this item’ error message ever stopped you when you were rushing to send an important email?

Don’t worry, you are not alone. This common problem can be frustrating, but the good news is that there are many solutions to get you back on track, including checking the email format.

In this section, we will guide you through the steps to fix the ‘Outlook cannot send this item’ error, which may sometimes be related to the email format, and get your email sending without any problem.

Change the text format from HTML to Rich Text

Outlook has three text formats: HTML, Plain Text, and Rich Text Format. Each format uses different coding.

Changing the message format can alter the content of your email by moving it within the coded email body, resulting in the displacement of escape characters.

This adjustment to the message format can be crucial in maintaining the integrity of your email’s content.

To do this, and ensure better management of email threads, make sure you are not composing your email from the Reading pane.

Click the pop-out icon to open a separate window for your email. This will give you a clearer view and more control over your email threads.

Follow these steps to change the text format from HTML to Rich Text in Outlook:

  • Firstly, open an Outlook conversation and click on Forward, Reply, or Create a new message.


  • Secondly, go to the Format Text tab in the new window.




  • Thirdly, select Rich Text from the available text formats.




  • Finally, enter the recipient’s email ID, body of the E-mail (if creating a new message), and click Send.




Removing long links would 9 out of 10 times solve the issue, as it would remove the potential escape characters from the email body. This is particularly effective in email programs where the email address formatting can be sensitive to such characters.

Alternatively, try sending shorter URLs or shorten the long URL using a URL shortener.

To do so, follow the below mentioned steps:

  • Secondly, enter the URL you want want to shorten in the empty field and click Shorten URL.


Outlook Cannot Send This Item

  • Thirdly, after shortening the URL, a new shortened version of entered URL will appear. Click the ‘Copy’ button next to it to copy the shortened URL to your clipboard.


Outlook Cannot Send This Item

  • In last, once the link is copied, paste it in place of the long URL.


Outlook Cannot Send This Item

Use Outlook web app

The problem of “Cannot send this item” especially arises when using Outlook on PC.

If you encounter this issue while sending emails, you can try switching to the web app version to see if that resolves the issue.

Use Microsoft 365 app updated channel

You should also check that you have the latest updates installed for Outlook and Microsoft 365 apps.

To do this Go to File > Office Account > Update Options and select “Update Now” to install any available updates.

Updates often include bug fixes and security patches to prevent problems like this.

Learn more about the Outlook app update channel and how to change it to semi-annual.

Repair outlook data file

Firstly, make sure that your Outlook data file is not corrupted. To repair your data file, navigate to ‘File’ then ‘Account Settings’ and select ‘Data Files’.

From there, select your data file and click the ‘Repair’ button.This will check your data file for errors and fix any problems.

Disable firewall or antivirus software

It is possible that your firewall or antivirus software is preventing Outlook from sending email due to bad hyperlinks, embedded hyperlinks, or third-party add-ins.

Try temporarily disabling your firewall and any antivirus software you may be running.

If this fixes the problem, you need to ensure that Outlook is added to the allowed programs list, and consider reviewing any embedded hyperlinks or third-party add-ins that could be flagged as potential threats.

Remove or update the problem causing add-ins

Installing add-ins can improve your experience with Outlook, but sometimes troublesome add-ins can cause problems.

To troubleshoot and identify if an add-in is causing the “Cannot send this item” error, you can run Outlook in Safe Mode.

You can check if the error persists by running Outlook in safe mode. If the error disappears in Safe Mode, it indicates that one of the add-ins is the culprit.

To pinpoint the problematic add-in, especially if it’s causing issues with additional email, blank email, or corrupted email, disable each add-in individually and try sending the email.

If disabling a specific add-in allows blank email or corrupted email to be sent successfully, that add-in is the likely source of the problem and should be investigated further.

To resolve the issue, consider updating or uninstalling the problematic add-in. Taking this step will remove the obstruction and you will be able to send emails without any hassle.

Check Email accounts settings

Double-check your email account settings in Outlook to make sure everything is configured correctly.

Go to File > Account Settings >. Select your email account and click “Change” to review the settings.

Also check: How to fix Outlook not responding?


Why does outlook say cannot send this file ?

Outlook is a popular email client, but sometimes you may encounter “Outlook cannot send this item” error message. There are a few possible reasons why Outlook won’t send your email.

File size is too large

The most common reason Outlook won’t send email is that the total size of the email, including any attachments, is too large.

Outlook and email services have size limits for sending and receiving email. If your email exceeds 50MB, Outlook will not be able to send it.

Some steps are mentioned below to resolve this issue:

  • To reduce the size of an email, remove any unnecessary attachments or content from it.
  • Zip or compress any large attachments to make them smaller. You can then send the zipped file as an attachment.
  • Use a file sharing service like Dropbox or Google Drive to share large files instead of emailing them. Provide the download link in your email.
  • Ask your email provider or network administrator to temporarily increase the size limit. Some services will allow a one-time increase if you have a valid reason.
  • Split email into individual smaller emails that are within the size limit. Be sure to label each email appropriately in the subject line, such as “Project Files Part 1 of 3.

Outdated email account or profile

If your Outlook profile or email account settings are out of date or corrupted, it can prevent email from sending.

It is a good idea to check for any updates to the Outlook app and to make sure your email accounts are working properly.

To update your Outlook profile and email accounts:

  • Firstly, open Outlook app and go to File > Account Settings > Update Profile.
  • Secondly, click “Update now” to install any available updates.
  • Thirdly, go to your email accounts and click on “Change” or “Repair” to refresh the account settings.
  • Fourthly, enter your email account password and click “Next” to update the account.
  • Finally, verify if the email sending issue has been resolved. If not, continue to the next steps.
  • To delete and recreate your Outlook profile, navigate to ‘File’ then ‘Account Settings’ and select ‘Delete Account’. Afterward, add your email accounts again.
  • To remove and re-add your email accounts in Outlook, navigate to ‘File’ then ‘Account Settings’ and select ‘Delete Account’.
  • Check with your email service provider to make sure there is no problem accessing your email accounts.

Software conflicts or File corruption

In some cases, software conflicts, file corruption, or other technical problems can prevent Outlook from sending email.

Repairing Outlook, resetting your network connection, or possibly uninstalling and reinstalling Outlook can help to resolve these types of problems.

If problems persist, you may need to perform a hard reset of your device or consult a technical support professional.

Also Check: Why is my Outlook not sending emails?


Conclusion

Are you tired of facing the frustrating “Outlook cannot send this item” error message?

We understand the importance of seamless email communication, especially when time is of the essence.

That is why we are here to assist you through the steps to resolve this error and ensure smooth email sending.

In this guide, we will provide you with step-by-step solutions to fix this issue and ensure smooth email sending.

We will cover various methods, such as changing the text format, using the Outlook web app, updating your Microsoft 365 app, disabling firewall or antivirus software, removing problematic add-ins, and checking email account settings.

Don’t let this error bother you. Let’s fix the “Outlook can’t send this item” problem so you can send your emails without any problems.

To know more about such topics visit assistme360.com


Frequently Asked Question’s (FAQ’s)

Why can my Outlook receive but not send emails?

There might be some problem in the email body or attachment because of which you are not able to send an email on Outlook. Try sending the emails with a slightly different body and without attachments.

Why doesn’t Outlook 2007 send the item when forwarding? 

Outlook 2007 cannot send an item when forwarding if there is some misinterpretation of one or more characters while decoding.

Why doesn’t my Outlook send the attachment?

Outlook might not be able to send an attachment either because of the big size or unrecognized format.


Content Writer

Smith Ron, the writer at Assistme360. He has extensive experience in crafting straightforward, step-by-step guides for technical issues. His broad knowledge ensures accurate solutions. Kindly spare a moment to drop a comment down and express your opinions. Your feedback can be valuable in assisting others who may come across similar problems.


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