How to Fix “Cannot Send This Item” in Microsoft Outlook

Last Updated on February 17, 2024

Outlook users have been reporting an issue on various online communities regarding a “Cannot send this item” error that they encounter. Although Microsoft has supposedly released a fix for this last April 2021, you may be one of those users who still experience this issue.

The “Cannot send this item” error in Microsoft Outlook started showing up for users on long email threads and when replying or forwarding emails with embedded hyperlinks point to website pages with long URLs.

To solve this issue, here are some fixes that you can implement, at least until you get the Microsoft update that will hopefully solve the problem for you.

Change the Email Format to Rich Text

One of the things that you can do to get rid of this error to change the email format from HTML to Rich Text Format (RTF). You can also use the plain text format.

Changing the format to text format will show the embedded links in text format.

To do so, make sure you’re not composing your email from the reading pane. If so, click the pop-out icon to create a separate window for your email.

Then, go to Format Text > More options > Message Format > Rich Text (or Plain Text).

Use the Outlook Web App (OWA)

For some reason, the “Cannot send this item” issue only happens when you’re using Outlook for PC. Meaning, if you’re experiencing the issue while sending an email, try switching to the web app version and see whether or not that solves the problem.

To do so, simply head over to the web app of Microsoft Outlook.

Change the Microsoft 365 Apps Update Channel

Without diving into the technical realm, what this fix basically does is switch to a different update channel (specifically, to the semi-annual channel) where the bug that may be causing the error has not been introduced.

Doing this will not require you to redownload and reinstall all your Microsoft 365 apps. When you change the channel, all those apps get updated automatically.

You can do this in two ways:

1. With Group Policy
2. With the Office Deployment Tool (ODT)

You can refer to Microsoft’s documentation page for more information regarding the steps you need to take.

Remove the Long Links

If you don’t want to go deeper, you can implement the easiest fix possible — removing the embedded links that point out to long URLs. However, this may not seem like the best move especially when the links are important.

On the bright side, you can always use the web app version of Outlook. If you insist on using the more powerful desktop version, then you can always change the email format to rich text or plain text.

That’s it! If you still have more questions regarding the issue, don’t hesitate to ask them down below in the comments section. You can also reach me directly by using the contact page.