Fixed: Outlook Cannot Send This Item

Users have been facing problems since the end of 2020 while sending emails from Outlook. Reportedly, the error message in Outlook says, “Cannot send this item”.

The matter has been in discussion on the Microsoft forum and is under investigation. However, many Microsoft experts have tried to give solutions, yet some users are unable to fix the problem because of the too technical language. Also, the information is diversified into multiple questions making it difficult for the users to troubleshoot.

We have compiled the information in such a way that it is easy to read and understand by the average user.

We have compiled all the information from the users’ experience, Microsoft’s expert solutions, and that we got from our own experts. In this article, we will share what we know about the “cannot send this item” error in Outlook along with the solutions.

Why does Microsoft Outlook keep saying “Cannot send this item”?

You might have faced the problem that it cannot send an item when sending, replying, or forwarding emails.

The error generally arises when the email body contains longs strings and URLs. Precisely, an escape character at the 2085th character place causes the email to not be sent.

What is an escape character?

An escape character is a character that causes an alternative interpretation in computing and telecommunication, such as an alphabet followed by a backslash (“\”).

The error looks like this:

Outlook Cannot Send This Item

How to fix “cannot send this item” in Outlook?

Now that we know why this problem occurs, we can develop the solution by eliminating the reason behind it.

You can either change the position of the escape character or remove the alternative interpretation of the text. Based on this, the following are the ways to fix “Cannot send this item” in Outlook 2007, Outlook 2010, Outlook 2013, Outlook 2016, Outlook 2019 and Outlook 365:

1. Change the text format from HTML to Rich Text

There are three text formats in Outlook: HTML, Plain text, and Rich Text Format. All these formats have different coding. Changing the text format would move the content of your email in the coded email body, thereby resulting in a displacement of the escape character.

What is the difference between HTML, Plain text, and Rich Text Format in Outlook?

As the name suggests, the plain text format can only be used to create simple text with no formatting, such as underlines, bold text, and custom text color. Whereas HTML and Rich Text Formats look the same, but the difference lies in the text coding. Also, the size of Rich Text Format files is slightly larger than that of HTML text files.

You cannot use text formatting with plain text format, so you have to choose either between HTML or RTF (Rich Text Format) for those beautiful-looking emails. If you are facing problems with the HTML text, we recommend you shift to RTF for that specific email. Furthermore, we recommend using HTML over RTF in the long term because of easier problem resolution and the small size of HTML.

How to change text format from HTML to Rich Text?

Use the following steps to change the text format from HTML to Rich Text in Outlook:

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

  2. A new window will open, go to the Format Text tab.

  3. Select Rich Text from the available text formats.

  4. Finally enter the recipient’s email id, body (if creating a new message) and click Send.

2. Remove Lengthy Links

Removing long links would 9/10 solve the issue as it would remove the potential escape characters from the email body. Alternatively, try sending shorter URLs or shorten the long URL using a URL Shortener.

How to shorten a long URL?

Use the following steps to shorten long URLs:

  1. Firstly go to a URL Shortener.

  2. Enter the URL you want want to shorten in the empty field and click Shorten URL.
    Outlook Cannot Send This Item

  3. A shortened URL will appear, click the Copy button next to it in order to copy it to the clipboard.
    Outlook Cannot Send This Item

  4. Once the link is copied, paste it in place of the long URL.
    Outlook Cannot Send This Item

3. Remove or update the problem causing add-ins

You can install add-ins to make working with Outlook easier. However, you may face trouble because of a problematic add-in.

To check if the add-ins you are using are causing any error, run Outlook in safe mode. If the “cannot send this item” error goes away, the problem is with the add-ins.

In order to find the problematic add-in, disable each add-in one by one and try sending the email. Successful sending of an email upon disabling a particular add-in means that the particular add-in is creating problems. Update or uninstall the problematic add-in to get rid of the problem while sending emails.

4. Try sending email using the Outlook web app

Use the Outlook web app or any other email client to detect if the error is from the client-side or the host (server) side. The successful sending of the email from another client means that the “cannot send this email” error was from the client-side, which is Outlook in our case.

If the problem is from the client side, either use another client or wait for the client to fix the problem, which may take long.

If the problem is from the server side, try running troubleshoot and following the other methods discussed in this article.

5. Change the app update channel

Well, this is quite technical to talk about if you are not a nerd. In simpler language, changing the app update channel to semi-annual would take you to the previous version when the bug was not reported.

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


After reading this article, you can get rid of the “Cannot send this item” message in Outlook. However, if you face any other problem while sending emails from Outlook, refer to why my Outlook is not sending emails?

These troubleshooting guide can help you eliminate the “cannot send this item” error in all the version of Outlook i.e., Outlook 2016, Outlook 2019, Outlook 365 and older versions.


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.

Leave a Comment