Can't send TO a Distribution Group "AS" somebody else

Have a weird issue I can't determine how to fix, and whether it's AD, Exchange, a bug in either or what.

But User A is trying to send to a Distribution Group "from" User B (User A is putting User B in the "from" box, and putting the Distribution Group in the "to" box).

When User A sends the e-mail, they get a bounce-back error:

From: Microsoft Outlook
Sent: Friday, February 28, 2014 10:57 AM
To: User A
Subject: Undeliverable: My Parents 2014


Delivery has failed to these recipients or groups:

DistributionGroup
You can't send a message on behalf of this user unless you have permission to do so. Please make sure you're sending on behalf of the correct sender, or request the necessary permission. If the problem continues, please contact your helpdesk.

I have verified in the Exchange Console that User A has "Send As" permission on User B, and that User A is listed as a Delegate in User B's Outlook > File > Account Settings Delegate > Delegate Access.
garryshapeAsked:
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David CarrCommented:
Have you tried removing and re-adding the Send-As permission?
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garryshapeAuthor Commented:
Yeah but got the same error. Unless I need to wait longer.

I'm going to try from OWA next.

If OWA doesn't work, I'm wondering if I need to add AD permissions to the DistributionGroup for both User A and User B, if such a permission is even possible.
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David CarrCommented:
Exchange permissions and AD permissions can be tricky to get working right
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garryshapeAuthor Commented:
Haha yeah, tell me about it. Will report back.
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ktaczalaCommented:
can user A send to distribution group as user A without any issues?
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MaheshArchitectCommented:
You can try to set Permissions through active directory

You need to enbale advanced features view in active directory in order to view security tab

Then replicate the changes through AD replication within all DCs in site as Exchange servers installed and check if it works
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garryshapeAuthor Commented:
Yes, User A can send to the Distribution Group as themself. Just not when changing the Froma ddress to a person they have Send As permissions to.

As for AD Advanced Features on User B's security properties, I show User A already is listed in there with "Send As" properties. Should I maybe also check "Allowed to authenticate" in advanced too?
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MaheshArchitectCommented:
No that is not required
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garryshapeAuthor Commented:
The issue appears to be a problem with our Exchange server, and I do not have a resolution for our particular situation at this time, as an admin has a case open with Microsoft who is still assisting. There may be some hotfixes involved but I do not know yet. I probably won't know for another month. Accepting general answers as a general solution here. If I find anything more helpful I will add to the discussion later.
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