Outlook 2010 client - One of the user's sent items email shows as from address as invalid address

Hi,
One of the user in exchange 2010 - outlook 2010 environment, in sent items email from address shows as invalid address after sent emails to recipients. Recipients are successfully received the emails. however, why the invalid address appearing in sent items
from address for the one of outgoing email?
EMail showing From: /O=FIRST ORGANIZATION/OU=EXCHANGE ADMINISTRATIVE GROUP (FYDIBOHF23SPDLT)/CN=RECIPIENTS/CN=users name On Behalf Of
username
thnaks
MD

Hi,
As what ManU Philip says, please check the issue in OWA firstly and try setting changes in Outlook.
Additionally, I noticed that there is an On Behalf Of in your post. If the issue is also the same on OWA, We can use the following command to check whether the user have Send on Behalf
permission on “/O=FIRST ORGANIZATION/OU…”:
Send On Behalf:
Get-Mailbox -Resultsize Unlimited | ?{$_.GrantSendOnBehalfTo} | select Name,GrantSendOnBehalfTo
Please try to remove these rights and restart Outlook to check the issue existing.
If all of the above fails, Please collect the error logs in Event Viewer and post here. I would like to help you any time.
Hope it helps.
Thanks,
Winnie Liang

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</Autodiscover>
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Thank You
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Hi,
How many users encounter this issue, all users with Outlook 2010 or some specific users?
According to your post, the Error code 600 indicates that your Autodiscover service is working well. as for the certificate mismatch issue, we can also following the KB below to resolve it:
http://support.microsoft.com/kb/940726/en-us
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