Outlook won't send messages except from default account

Posted on 2013-01-24
Last Modified: 2013-02-18
I have a new account that I created in Exchange. MYDOMAIN\drdamnit the smtp address I gave my main domain user (MYDOMAIN\CaptainAwesome) Send As and Full Access permissions to the drdamnit mailbox.

When I configured outlook, I added the account, and just typed in, and clicked next. Outlook queried AD, got the information, and autoconfigured the account.

I can receive fine. Outlook opens.

When I click New > Email, I get the email form as normal, and have to click the "From" button to select which account I am sending from. I select the drdamnit account.

I compose theemail, and hit send.

THen it goes to the outbox of that account, and just sits there. Mocking me. It doesn't send. It does nothing.

Open it again? Sure. Click send again.

Again... nothing.

My email is having an existential crisis. I need an answer before I become a real head case.

Question by:DrDamnit
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LVL 47

Expert Comment

ID: 38817018

So Captain Awesome is the main account

You created an Entirely New AD User w/Mailbox called drdamnit
You gave yourself Full Permissions to it, as well as send as...

Looking at your tags i see you have outlook 2010

So when you added Drdamnit to your account
You didn this by closing outlook
 Going to control panel>Mail> Accounts

Selecting add New Account
Manually Configure
Exchange Account
Enter DrDamnit user it
Check name against exchange server
Then finished the user accoutn setup as you would a normal account

Now when opening outlook once should see both accounts on the left

Becuase you are using outlook 2010, and you have full permissions on this account
Outlook 2010 should simply treat it as a 2nd exchange acccount

Not an additional account, so send as is not reallt required....

You should only need to select/highlight drdamnit*
Select New email, From SHould be drdamnit
Then send and it should go

if it doesnt, I might try removing the send as permissions from the ad account
Since you have full permission on the account already....

might be getting confused

The only way i see thee could be some issues is if the drdamnit account was setup as an additional account not an Exchange account

You would see this if you went into your Captainawesome account properties>more settings>Under advanced Tab, you would see drdamnit
LVL 32

Author Comment

ID: 38817191
It's definately setup as an exchange account. I did not set it up manually, in OL2010, on the first screen, it asks for your name, the email address, and the password. But since it is exchange and my main account has full permissions, i just enter in the as the email address without entering anything else, the next button gets enabled, and I click next. It sets itself up.

I do have to restart outlook after doing it (i think), whcih I do.
But the outbound emails are just getting stuck. They dont' send.

They send from the main account just fine.
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 38818957
If it was permission based, it would bounce.
The first thing I would do is try it with another machine. That will confirm if the problem is specific to that machine.

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LVL 32

Author Comment

ID: 38819198
Update... One did send, (apparently). I got a delivery delayed message. It says that it will continue to try to deliver this message for 1 day, 23 hours, and 39 more minutes and then give up.

Exchange cannot deliver messages to itself? That's odd.

Another test message still sits in the Outbox....
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 38819358
If the message is stuck in the queue, then look in the queue viewer to see what the reason for the message delivery problem is.

LVL 32

Author Comment

ID: 38827053

I decided I wanted to test to see if the problem was outlook or server / ad /exchange related.

So, I logged into the web interface for the new email address. I was able to successfully send and recieve email from that account. Replies worked, everything is fine as long as I am working in the web interface.

To me, this means taht it is not an exchange problem, it's an outlook problem.

So, I deleted the account from my outlook profile, closed outlook, went back into mail32 in the control panel, re-added it, unchecked "USe cached mode" so I was working with the live version on the server, then re-opened outlook.

No joy.

When I create a new email, then change the from to the new email address instead of my main account, and attempt to send an email, it just sits in the outbox....

LVL 32

Author Comment

ID: 38827157
Another update...

I have other exchange accounts setup in Outlook. Normally, when I hit reply from one of those accounts, the new message bears that alternate address in the from field. So, if i receive an email on that account, the reply comes from that account automatically.

However, with this new account, it defaults to my default account when creating a reply instead of showing the new account as the from field.

The plot thickens...
LVL 32

Author Comment

ID: 38827222
I decided to go scorched earth.

I ended up backuping and deleting %userprofile%\appdata\local\microsoft\outlook AND %userprofile%\appdata\roaming\outlook.

Then I deleted everything in mail32 control panel, and re-setup a new profile.

I can now send and receive mail from both accounts in Outlook; however, something strange is going on... there should only be TWO accounts on the left side of my Outlook in file view mode. There are 7 (all the accounts I previously had).

Where is Outlook looking to get these accounts and their information?

After doing this, and re-adding in the alternate (new) email address in question, I have decided the problem was a stale email address in the From dropdown. Killing the accounts and re-adding them did a fresh query to AD, and allowed me to add it and it now works.

But there appears to STILL be a problem with the profile.

LVL 47

Expert Comment

ID: 38829081
Check you account settinngs just to be sure there not extras added

Also have a look under accoutn settings
Look under Datafiles and see how many are listed here

Might also look at More Settings and make sure additional mailboxes havce not been added

Could also try to open outlook using
Start>Run>Outlook.exe /safe

See if they are loaded here
If they arent close and reopen, and see if they come back
LVL 32

Accepted Solution

DrDamnit earned 0 total points
ID: 38904196
I ultimately scrapped the profile using the steps in my post above, and disabled using cached mode.
LVL 32

Author Closing Comment

ID: 38904197
No solutions fixed the problem. The profile had to be scrapped, and then cached mode disabled.

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