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Last Updated: April 4, 2023


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.”


The issue is fixed after installing the appropriate updates for both Outlook Desktop and Windows. 

This issue is fixed in Outlook Desktop build 16116.10000 and increases the URL limit from 2084 to 8192 characters.  The Outlook Desktop fix is enabled at 100% of Current Channel as of April 4, 2023.  Monthly Enterprise Channel will get the fix when it updates to Version 2302 (Build 16130.20218) and higher.  Please see Update History for Microsoft 365 Apps (listed by date) to track which versions are at which channels.

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.


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


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

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