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swilliamson-mwnsFlag for United States of America

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Exchange 2010 Coexistence with Exchange 2016 Mail stuck in Outbox

We have a Coexistence environment with Exchange 2010 and 2016.  I migrated two mailboxes to the Exchange 2016 Server and those two mailboxes cannot Send mail (internally or externally)
Those messages get stuck in the Outbox.
Any suggestions?
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Valentina Perez
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Hi Swiliamson,

Have you configured a send connector in Exchaneg 2016?

Regards
Valentina
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Yes, one actually came over automatically from my Exchange 2010 environment.  All the settings appear to be appropriate.
Where is the outlook anywhere pointed?
Outlookanywhere should point to Exchange 2016. i.e. mail.domain.com should point to IP of Exchange2016.
Fir testing you can add a host entry and in the PC in which this mailbox/outlook configured.
https://support.rackspace.com/how-to/modify-your-hosts-file/
Your outlook interface should be Exchange 2016.  Exchange 2016 will proxy/redirect all the connections to 2010.
BTW your Exchange 2010 users should be connected to Exchange 2010 by CAS server/CAS array as Exchange 2016 is not aware of MAPI/TCP connections.
It is pointing to webmail.domain.com  I have the appropriate DNS entry point to our exchange server.  
I have the authentication method set to "Negotiate"
HI swilliamson,

If you connect in OWA, do you have the same behaviour?
almost the same behavior, but instead of messages going into the "Outbox" they are placed in the "Drafts" folder
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Valentina Perez
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open the EAC and navigate to “mail flow” -> “receive connectors”. Double click “Client Frontend “. Go to the “security” tab and under permission groups, tick “Exchange servers”. Click “save”.
Try this
I checked that setting and I have the following checked already. "Exchange Servers" "Legacy Exchange Servers" and "Exchange Users"
Please try to delete the emails in outbox and try sending new email.
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Enough information to confirm as answer.