some sent emails are missing and moving to "recover deleted items"

[spring8080]

hello , we are using on-premises exchange server 2016 in my environment.

and we are using microsoft outlook 2019 & 2021 .

i have one question :

i notice that the sent emails for all users are appear in "recover deleted items" , however these emails are not deleted and still exist in sent items folder  . so it is appear the same emails in "sent item" folder and in "recover deleted items" , which i think very weird .

i have one incident :

one of my user is encounter a weird problem , that some sent emails are  weirdly disappear from "sent item" folder but he never delete them , and we can found these items in "recover deleted items" , but the restore option in "recover deleted items" didn't restore the email to the user mailbox .

however i don't have any problem mention in healthreport for my exchange server , all in good condition .

what may be the problem ?

[#2]

@spring8080 

Sorry for the inconvenience or delays this issue may have caused you. Just like you have mentioned that emails from the sent items folder are moved into the recoverable items folder for users in your organization.

To start troubleshooting, could you please let me know when the issue started? Was there any recent changes that you are aware of? Is the issue reproducible when logged into the web version of outlook? Are they logged into the updated version of Outlook? Do they make use of Outlook on their mobile devices?

There could be a chance that a rule has been mistakenly setup on their app devices, hence causing the automatic deletion. Can they remove their account permanently oh their mobile devices and observe if the issue will be reproduced? How often does this happen? Does it occur with new set of emails, emails from particular domain or all emails (both internal and external organization)? Do we have working users? What is the difference between the working users and the non working users?

Let us also confirm if there is a rule triggering the effect of the email disappearance. This can be confirmed from the user end and also from the exchange admin console too. Does the issue occur when logged in to another machine of a working user?

Please feel free to respond at your earliest time to continue to work with you. Thank you!

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[#3]

@Deleted these the answers for the questions :

could you please let me know when the issue started?

the user who get this problem notice that 1 month ago , it happened with him around 3 times

Was there any recent changes that you are aware of?

nope, only i update the windows server 2016 using "windows update"

Is the issue reproducible when logged into the web version of outlook?

he is using desktop version of outlook only

Are they logged into the updated version of Outlook?

it was microsoft outlook 2019 , i update recently to microsoft outlook 2021

Do they make use of Outlook on their mobile devices?

yes

Regarding the rules , he has many rules , but i check them , nothing related to moving or deleting emails from sent items.

Can they remove their account permanently oh their mobile devices and observe if the issue will be reproduced? 

ok i will inform him to do that

How often does this happen?

3 times in this month

Does it occur with new set of emails, emails from particular domain or all emails (both internal and external organization)?

new set of email emails , it happened when he sent email to internal users

Do we have working users? What is the difference between the working users and the non working users?

i didn't understand what you mean by "working users"

This exactly what happened :

it happened with him 3 times , while he is working in excel file and then choose file , share , email , send as attachment and he choose a recipient to send this excel file to him , after he sent , the recipient receive the email but this email not appear on the sender "sent item" folder , however he can found this in "recover deleted items" , the restore option does not restore the email  .

and also regarding my question :

is it normal for emails in "sent items" to be appear also in "recover deleted emails" , i found the same for many users , same email appear on "sent items" and on "recover deleted items" , but not every sent emails are appear there but most of them .

is it normal ?

[#4]

@spring8080 

When I say working users, I mean users who are not affected by this.

It is not normal that emails that appear in the sent items folder to also appear in the recoverable items folder. This must be an outlook misconfiguration. Can you confirm the behavior after the accounts were completely removed from their mobile apps.

Outlook is probably generating copies of sent items which is getting deleted. So, we need to confirm, if normal sent items are showing in the deleted items folder (not the one that occurs while working with Excel File).

In addition, check if the Don't save copies of sent items check box is unchecked. If it is unchecked, try checking it following the steps below:

• On the File menu, select Account Settings > Account Settings.
• Choose the IMAP, and then select Change.
• Choose the Don't save copies of sent items check box.
• Select Next, then Done.

Try all of this and let me know if issue is resolved. Thank you!

If I have answered your question, please mark your post as Solved

If you like my response, please give it a Like 

Appreciate your Kudos! Proud to contribute! :)

[#5]

Hi @spring8080  - There is a possibility that the messages that you see in the Recoverable Items folder might be a copy of the draft that was saved when the user was composing the message.

Regards

Dhruva

[#6]

@Deleted , as i mention before , i am using exchange account not imap account

[#7]

so you think it is normal ?

[#8]

@spring8080 I have the same issue with brand new Exchange 2019 CU12 and Outlook 2016.
But what I noticed is that during the weekend when clients are not connected, the emails are not going to Recover Deleted Items. So I think in my case the issue is caused by the Outlook client. Tell me if you managed to resolve your issue. Regards.

[#9]

@GPetkov  

Hi we've got office 365 , deleted all the users Rules. When she creates a new Rule the email is diverted to the correct directory. 5 Minutes later the email is in " Recover Deleted items " 

Any advice , I can't seem to resolve this problem 

[#10]

Hi Leon_Nel,
try deleting the user's Outlook profile, cleanup Outlook profile files from C:\Users\Leon_Nel\AppData\Local\Microsoft\Outlook and setup a brand new profile with new data file. Also try setting exclusion in the AV for this Outlook path where the data files are stored.

[#11]

@Leon_Nel 

In some cases seems the emailjunkconfiguration to have caused this behavior, check by running following command:

Get-MailboxJunkEmailConfiguration <MailboxIdentity> | Format-List Enabled

and try disabling it for the affected user:

Set-MailboxJunkEmailConfiguration <MailboxIdentity> -Enabled  $false

Monitor whether the mails are still being moved in Recover Deleted Items.

In my case only the sent mails are landing in Recover Deleted Items.

And disabling the mailbox rule for junkemailconfiguration didn't help.

[#12]

This is a fascinating thread. We are also moving over to Exchange 2019 but with Outlook 365 licensing. I originally thought my users were just making mistakes, but I can confirm even IT staff are having the issue.
What we see are specifically Sent Items missing from that folder; they are in the Recover Deleted Items folder instead. When they are restored, they go to the Archive folder for some reason. Archiving is disabled, and there are no Rules to produce this.
I'm currently working on the theory that it's only remote users having the issue, I'll report any more findings back here.

[#13]

@TWagner Any updates on this?