Outlook: Fix for "Cannot send this item", Send mails are missing

[German]Microsoft Outlook users and administrators sometimes struggle with the fact that the program does not always work reliably. Sometimes e-mails are not sent. In other cases, the mails are not sorted in the Sent folder or two program starts are required. I have listed two cases and their solutions.


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Send bug in Outlook fixed

In the Microsoft Answers forum the “cannot send this item” bug in Microsoft Outlook has been discussed since February 2021. A user reported that his Outlook shows the message “cannot send this item” every time he tries to reply or forward a mail as HTML. The whole thing also does not work when he tries to save message and send it afterwards. The bug has been confirmed in the forum by many affected people.

Within the forum thread is asked at the end of March, beginning of April 2021, whether the bug had been eliminated by the monthly Office updates. Microsoft had published a support post Outlook error “Cannot send this item” when replying to an email  as of March 25, 2021 and marked the bug as fixed.

The bug can occur when the 2084th character in a link is an Escapes character. This problem can also occur with long URLs and when processing with SafeLinks. Microsoft provides instructions on how to work around the issue in the support article. In the Microsoft 365 update channel, where users, get monthly updates, a fix should be rolled out automatically. I had already noticed it at Bleeping Computer in early April 2021, but didn’t address that on the blog.

Sent mails disappeared

And then there’s the bug of sent mails disappearing and not being found in the Sent folder in Outlook. I stumbled across this error description again on Facebook over the weekend. Here is the translation

Exchange 2019 on Premise

Sent mail disappears and can’t be found in Outlook. Solution: recreate Outlook profiles.

Weird: On Android with Nine, the problem does not exist.

The problem occurs more often

I had already noticed this thread at German site administrator.de some time ago (didn’t have time to address it here on the blog yet). A user there describes a rather strange error pattern in Outlook 2019 (Office Home & Business with POP3 account):


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Mails to be sent stay in the outbox until you press Send/Receive. After that, the mail is sent (also arrives at the recipient), but does not appear in “Sent Items”. In parallel to the problem, the “Auto Complete” feature does not work when entering an email address. If Outlook is closed and reopened, everything works as usual. Closing and reopening it again causes the error. The problems occur exactly every second start of Outlook.

The usual attempts to solve the problem with installing updates, having Office repaired, deactivating add-ons, a new profile did not lead anywhere. Exactly every second start of Outlook showed this behavior. The solution was posted by someone in the Spiceworks community in the article Outlook not putting copy of email in sent folder.  Laird Spicehead wrote:

Check the following setting File -> Options -> Mail -> Save messages

There is a setting When replying to a message that is not in the Inbox, save the reply in the same folder.

If the user has moved the email to another folder before replying and the above setting is active then the reply will save to that folder not to Sent Items.

And there is another solution, posted by user Will320:

Think I may have found the culprit that is causing the issue. Try unchecking the  Store my Outlook settings in the cloud under options -> general, then set your settings back under the options -> mail -> sending messages area.  Just in case it isn’t the culprit with watch it through the next couple of days and will post the results.

This option apparently causes the Outlook client not to store the sent mails in the Sent folder, because it assumes that they are in the cloud (which is not the case with on-premises solutions – so the option my be available only in Office 365 modules). Perhaps it will help those affected.


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