Exchange 2013 send as distribution list issue

Hi all,

I'm looking for help or suggestions relating to an issue that has several of us stumped.

We have a client running Exchange 2013 who is having issues sending as a distribution list that they have set up. The user in question is with the distribution list being

> Bob has send as and send on behalf of permissions for
> Bob is also an owner of the group

If Bob logs into OWA and sends as then the mail goes fine, there are no issues and the mail is received fine both by internal and external recipients, showing as having come directly from

If Bob sends the email from his Outlook 2013 profile and either types the email address to send as ( or goes into the global address list and selects the "info" group, the mail just sits in his outbox. I've seen this behavior for other reasons in the past but to clarify it's ONLY mail he's sending as the distribution list that does this, others go fine.

The funkiest thing is, if Bob then drags those mails out of his outbox and into his drafts and logs onto OWA again and tries to send them from there, the "from" address shows as being populated by an Exchange distinguished name rather than as the name or email address of the list in question. When this is deleted and the email address put instead it then sends fine from OWA.

I'm guessing the reason for the failure is therefore something to do with the distinguished name being pulled from somewhere and used for sending the mail. If I edit the mail in OWA and click send straight away with the distinguished name still in place it gives an "Invalid Recipient" error (yes, recipient, even though it's the from address).

error screenshot
This is a screenshot of the error and the distinguished name appearing when Bob drags the message into Drafts in Outlook and then edits it in OWA.

Whilst I suspect the issue must have something to do with the distinguished name (given that it sends fine when i overtype it with the email address) I can't explain why Outlook is using it or why it seems to register as invalid in OWA.

I've run through things I can think of as obvious, such as updating the GAL and OAB on the local machine but these are showing as up to date. I've force updated it as well as making changes and seeing these represented in Outlook before sending, but the results are the same. The profile is not running in cached mode, but live against Exchange 2013.

Does anyone have any ideas or thoughts that might assist? It's a complete mystery to me!

Many thanks.
Who is Participating?
Md. MojahidConnect With a Mentor Commented:
The workaround to this issue is using Outlook in cached Exchange mode for now. Official Fix might be released later.
Simon Butler (Sembee)ConsultantCommented:
"Bob has send as and send on behalf of permissions for"

Don't set both.
One or the other. Either Send As or Send on Behalf of.

Was this a migration? Did the group exist before the migration?

Robox1Author Commented:
Hi Simon,

I'll remove one and then the other and test as a potential solution. This was not a migration; this was a fresh setup. The company do not have many PCs and are not domained, they connect to Exchange using OAW utilising Outlook's HTTP proxy settings. The setup works in every way except this.

I must admit, this is also not the first time we've had issues with sending as on Exchange 2013, inside our own company we also have an individual who needs to send as another company employee and since moving from Exchange 2010 where this just worked, and flawlessly, it now doesn't. Not wanting to muddy the waters however, my main priority is the distribution list above. It just seems odd that it works fine in OWA but not at all in Outlook.

I'll report my findings after testing the above.
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