outlook Message "cannot send this item"

Anonymous
2021-02-09T08:13:59+00:00

Hi to 

As of yesterday my outlook is popping the above message every time I try to reply or forward a mail as HTML. i even try to save the message and send it after but even that does not work.

Can you please help

Outlook | Windows | Classic Outlook for Windows | For home

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments

43 answers

Sort by: Oldest
Most helpful Newest Oldest
  1. Anonymous
    2021-03-19T10:47:16+00:00

    Microsoft,

    Please sort this as soon as possible, we are a small business and my other users are not tech savy so this is causing a lot of problems. I cannot believe how flaky the Microsoft products are now. Please stop changing things for the sake of change. I could go back to outlook from 1997 and have a better experience and be able to see folders down the side more clearly because they are colored yellow and stand out.

    Please inform me when there is a fix and how to download it.

    Was this answer helpful?

    3 people found this answer helpful.
    0 comments
  2. Anonymous
    2021-03-26T10:20:54+00:00

    We have encountered the same issue with 'Cannot send this item' errors appearing when replying\forwarding messages.

    It appears to happen when the message content contains a chain of messages, which will have URLs in signatures that have been rewritten by Sophos Mail Gateway. One suggestion has been to turn off the URL rewriting but we have yet to test this.

    I have, however, just tested a message from an eml file which was unable to send, and unfortunately the latest beta channel build 13919.20002 does not appear to fix this issue. The same 'Cannot send this item' appears.

    What the root cause appears to be is either the number of URLs in the message body, or the combined length of all URLs - since rewritten URLs tend to be of a considerable length. I'm hoping to test this next by replacing previously rewritten URLs and testing. The combined length appears to be more likely as removing longest URLs first one by one until the message sends appears to resolve the issue with less removed than removing shorter URLs.

    Many thanks,

    --Richard Allan

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  3. Anonymous
    2021-03-26T10:48:52+00:00

    We are seeing the same behavior.  Disabling URL Rewriting may help future emails but does not fix emails that we already have in place and have been testing with.  

    Following this thread.

    Was this answer helpful?

    0 comments
  4. Anonymous
    2021-03-26T14:52:40+00:00

    simply switching the format text from html to rich text worked for me as a work around - found this video on youtube.

    https://www.youtube.com/watch?v=45HgJP3trBo

    Was this answer helpful?

    0 comments
  5. Anonymous
    2021-03-31T15:45:43+00:00

    It is insane that Microsoft doesn't have a solution for something an dominant at Outlook. That being said, what is the down side to disabling rewriting of URLs as a working around to this problem?

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments