send as works in OWA, but not outlook client

We have 2 domains in our company.  I setup a corresponding distribution group for a users email account so he could send an email from either domain address. (example:  John.Doe@ficticiousdomain.com is the email account, John.Doe@ficticiousdomain2.com  is the corresponding distribution list)

In OWA john.doe is able to send as the corresponding distribution list.  However, when trying to do so in outlook 2016 client, user gets a message undeliverable bounce back.  Error is [0x80070005-0x0004dc-0x000524]

Any ideas over how to configure the outlook client to make this work?
tike55Asked:
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imkotteesSenior Messaging EngineerCommented:
If jone.doe has got send as permission on this DL, try downloading address book and send.
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tike55Author Commented:
already tried that
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masnrockCommented:
You could try deleting everything related to offline address books, which will force it to reload. Also, did you hide any of the email addresses involved from the GAL?
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tike55Author Commented:
I don't want to delete offline address books.  Im sure they have a lot of local contacts, it is HR so I don't even want to go there..

I didn't hide any of the email addresses either.
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masnrockCommented:
Delete and ready the permission or delete the other address from autocomplete cache. It is also possible that the issue is purely a 365 obe. People have mentioned having the issue, and it suddenly just goes away.
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tike55Author Commented:
We already tried deleting the other address from the autocomplete cache.  It didn't work.

Could you further explain what you mean by "delete and ready the permission?"
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tike55Author Commented:
What about if I try to add the user as an owner?
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masnrockCommented:
Sorry, autocorrect nailed me when I use using my phone. I meant delete and READD. Feel free to try adding the user as an owner, but won't 100% guarantee that it will work.
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