outlook Message "cannot send this item"

Hi solonstampoulis,

Good day. Thank you for posting in our forum.

To isolate whether this is a client side or an account side issue, please check whether you can reply or forward a mail on the Outlook Web App.

Meanwhile, let create a new Outlook profile, add the email accounts, then perform reply or forward and check if it works as expected.

You may refer to the following article for instructions on how to a create new profile. Meanwhile, please check the updates of Outlook.
http://office.microsoft.com/en-us/outlook-help/create-an-outlook-profile-HA102749460.aspx?CTT=1 

If the issue persists, could you please provide us the error message and the email in the private message ?  In addition, may l know if all the messages you try to reply have this issue? We are happy to do more research for you. Thank you so much.

Best regards,

Nerissa

have had 6 user have this same problem with in the last two days .outlook Message "cannot send this item  when trying to send a email.  I tired changing the format of the email to rich text and rebuilding their profile nothing work.

I started having the same issue in my environment.  I am probably up to 50 people.  I have not been able to find a fix.  The rich txt workaround seems to work but its just a work around.

Hi team 

I have already try everything you suggested but the problem is still there. 

Do you have any update?

Hi solonstampoulis,

I am so sorry for the late reply since I was out of office.

Please run outlook in safe mode and check the issue, it can tell us if the issue is related to add-in issue. If the issue is solved by that, please disable the add-in one by one to check which one is causing the issue. How to open Outlook in sage mode: https://support.microsoft.com/en-sg/help/4026478/outlook-open-outlook-in-safe-mode.

If you install Norton Antivirus on your PC, the best way to resolve it is to simply disable the script blocking feature in Norton Antivirus.

If you don't have Norton Antivirus downloaded on your PC, please try disabling the new-mail notification feature in MS Outlook. Many users reported the error was solved by that.

Please run the Windows Registry tool to detect if there are any invalid registry entries. Here is an article about description of the Windows Registry Checker Tool (Scanreg.exe): https://support.microsoft.com/en-us/help/183887/description-of-the-windows-registry-checker-tool-scanreg-exe

If the issue still persists after steps above performed, please send us a screenshot of the detailed error for us to further analysis, thanks.

Best regards,

Nerissa