Exchange 2007/Outlook 2013: Distribution Group SendAs Issue

I have an annoying weird issue where doing a SendAs with a DL only works if picking the address from the GAL. However if the second time I pick it from the now cached entry, it tries to do a Send on Behalf.....which of course is denied and I get an NDR. Of course have had no luck searching forums or the Internet.

Here is the current environment:
2008 Forest and Domain
Exchange 2007 SP3
Outlook 2013

This issue of course only occurs in Cached Mode. I have gone so far to even delete the Outlook OAB file and redownload it. Again this works every time, even in cached mode, when I pick the address from the GAL. Just for some reason tries to send with Send on Behalf Of permissions which choosing it from the cached entry in the auto-complete list.

Is this just one of those weird rarely known issues? FYI: I am looking for a fix.....if there is one.....not a work-around or unsupported fix.
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SilverwolfSenior Server EngineerAsked:
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SilverwolfConnect With a Mentor Senior Server EngineerAuthor Commented:
Update:

Turns out the issue was do to the OS for the CAS server being corrupted. Had to setup a new VM and then restore Exchange to it. Worked fine after that.
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Serena HsiMarketing ConsultantCommented:
It would appear that this issue comes up frequently, regardless of the version of Outlook. It's like this recurring bug that never gets fixed from version to version. You'd think that after n-iterations of the application, the fix would get in eventually...

Here is what Microsoft suggest for Office 365 "Send As" error for sending.

Here is how to clear the caching issue for Outlook 2010.

And some other suggestions on the fix
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SilverwolfSenior Server EngineerAuthor Commented:
Serena,

Thank you however those don't work or apply in my situation. The first link refers to only a feature in Office 365 or Outlook 2016. The second link doesn't apply because it is talking about a mailbox, not a distro list. Also I stated in my initial question that I have already cleaned the Autocomplete cache. The other suggestions also do not apply and are already things I have tried.
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SilverwolfSenior Server EngineerAuthor Commented:
Only one suggested solution provided, which I had stated in my question that that was tried. Also my notes showed that the suggestions given did not relate in anyway. However it mostly was due to my issue being caused by a corrupt OS, which none of the suggestions relayed to that issue.
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