Sign in with Microsoft
Sign in or create an account.
Hello,
Select a different account.
You have multiple accounts
Choose the account you want to sign in with.

Last Updated: November 10, 2023

ISSUE

When you reply to an email that has long links in the body, Outlook may display the following error:

Microsoft Outlook error message, Cannot send this time.

Outlook will display the error 'Cannot send this item' when the 2084th character in a link is an escaped character. This situation can occur with long URLs and when processed with Safe Links. When Safe Links wraps the URL it exceeds the 2084 Outlook limit for URLs and the URL gets truncated. 

Other common symptoms with this issue include: 

  • URLs are truncated and when you click on them you may see a 404 Error.

  • When you click on a link, Microsoft Defender may display an error message “The page that you are trying to access cannot be loaded” and “Due to an internal error, this web page could not be loaded. We recommend that you close this page.”

STATUS: FIXED

The issue is fixed after installing the appropriate updates for both Outlook Desktop and Windows. This issue is originally fixed in Outlook Desktop build 16116.10000 and increases the URL limit from 2084 to 8192 characters.  

This issue is fixed in Outlook Desktop in the following channels. Please see Update History for Microsoft 365 Apps (listed by date) to track which versions are at which channels.

Current Channel – Fixed in Version 2302 (Build 16130.20218)
Monthly Enterprise Channel – Fixed in Version 2302 (Build 16130.20394)
Semi-Annual Enterprise Channel (Preview) – TBD, Backport in progress
Semi-Annual Enterprise Channel – TBD, Backport in progress
Semi-Annual Enterprise Channel Extended – TBD, Backport in progress

In addition to the Outlook Desktop update there is also a dependency on a Windows fix. The following Windows versions and updates include the fix.

OS

Release Update

Win 10 20H2

KB:5022834 and newer

Win 10 21H2

KB:5022834 and newer

Win 10 22H2

KB:5022834 and newer

Win 11 21H2

KB:5022836 and newer

WORKAROUND:

To work around the issue, you can do one of the following:

More Resources

Icon Experts (brain, gears)

Ask the experts

Connect with experts, discuss the latest Outlook news and best practices, and read our blog.

Outlook Tech Community

Icon Community

Get help in the community

Ask a question and find solutions from Support Agents, MVPs, Engineers, and Outlook users.

Outlook Forum on Answers

Icon feature request (light bulb, idea)

Suggest a new feature

We love reading your suggestions and feedback! Share your thoughts. We're listening.

Find out how

Need more help?

Want more options?

Explore subscription benefits, browse training courses, learn how to secure your device, and more.

Communities help you ask and answer questions, give feedback, and hear from experts with rich knowledge.

Was this information helpful?

What affected your experience?
By pressing submit, your feedback will be used to improve Microsoft products and services. Your IT admin will be able to collect this data. Privacy Statement.

Thank you for your feedback!

×