Outlook 2010 w/Multiple Exchange Accounts Won't Send From Second Account

I am having an issue using two MS Exchange email accounts (each one on a different server) within Microsoft Outlook 2010. I am able to recieve email from both Exchange accounts, but I'm only able to send email using one of them. When attempting to send email from the second account, the email just remains in the Outbox and won't send.

It seems that, upon opening the program, whichever email account sends the first outgoing message is the one that will actually send email - the other email account just retains the message in the Outbox. For example:

If I open Outlook and compose a new email using mail@domain1.com, that message will be sent - and I can continue to send email through this account. However, if I try to send a new message (or reply to a message) using mail@domain2.com, the message will not be sent. However, (usually) if I close Outlook and re-launch it, the mail@domain2.com account will send the message(s) in the Outbox, and I'll be able to continue sending email using this account - but if I try to then send an email using the mail@domain1.com account, it won't send.

I've had this issue before with Outlook 2010, but then it went away and I was able to use both accounts without any problems. I don't remember what (if anything) I did to resolve the problem before.

One of the Exchange accounts uses a local server (running Small Business Server 2008 w/Exchange Server 2007). The other Exchange account is located on another server which I don't have control over. I doubt that this is a problem, since I've also tested this problem accessing two Exchange accounts located on the local server and had the same problem.

I am desperate to figure this out. Setting up another profile for the second Exchange account is not an option - I need to be able to access both accounts from the same profile.

Thanks
savetheorcasAsked:
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pvernocchiCommented:
What if you create the profile with only one account? Does it happen?

Did you try running scanost.exe to the file involved?
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savetheorcasAuthor Commented:
What do you mean "create the profile with only one account"? If I understand you correctly, you're asking if I have any sending problems when using a single Exchange account in a single profile - in which case, no, the problem does not occur.
As for the scanost.exe question, I've never heard of it and wouldn't know how to run it.
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pvernocchiCommented:
Sorry, take a look at http://office.microsoft.com/en-us/outlook-help/about-the-ost-integrity-check-tool-HP003089624.aspx

So the email is queued in the Outbox folder ONLY when two Exchange accounts are configured in the same Outlook profile. am I right?
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savetheorcasAuthor Commented:
Correct. Like I said, I had this issue before then it went away, now it's come back. I actually restored my computer back to a previous backup and tried it again, but I just got the same error. It almost seems as though Outlook doesn't even TRY to send the email from the second account. When I send an email from one account, it actually shows (at the bottom) the send/recieve message, whereas with the other account it shows nothing.
 
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savetheorcasAuthor Commented:
I looked at the link you included in your reply regarding the OST integrity check tool, but I don't seem to have that file anywhere on my system. I looked in C:\Program Files\Common Files\System\ and there is no MSMAPI folder. I also looked in C:\Program Files (x86)\Common Files\System\MSMAPI\1033, which does exist, but the only file located in the folder is MSMAPI32.DLL.
The only thing even close is a file called SCANPST, which is located at: C:\Program Files (x86)\Microsoft Office\Office14.
A search on the C: drive also couldn't find the scanost.exe file.
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JuusoConnectaCommented:
Can one mailprofile in outlook 2010 withhold 2 exchange mail accounts within the same mailprofile? (if yes, can it be against 2 different excahnge servers?)

I was under the impression that outlook only (undependent of which version) only support one exchange account within one mailprofil, and if you want to set up a second mail account (which in this case seems to be Exchange aswell), it needs to be setup as IMAP.

To be able to receive mails correctly to bouth mailboxes and "send from" function work properly, you will need to configure advanced settings in you secondary (the second added mailaccount, which is exchange accoutn aswell) mail account and specify the servername (which should be the webmail in this case) and specify the user and password ?

Let me know if Ive missunderstood the problem ?
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pvernocchiCommented:
JuusoConnecta: Outlook 2010 can have two Exchange accounts from different servers.
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pvernocchiCommented:
Since I can't find it neither, you can try deleting the ost file which is in your Windows profile. You'll have two ost files, one per Exchange account. Just delete the second account ost.

Regards,
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JuusoConnectaCommented:
Thanks for the inco pvernocchi =], didnt know that,

regards
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savetheorcasAuthor Commented:
Thanks everyone, the problem still exists even after deleting the OST files. Like I said, Outlook doesn't even look like it's trying to send the email.
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savetheorcasAuthor Commented:
I finally fixed this - but it's hardly worth mentioning. Basically, I re-installed Windows 7 and started from scratch. Works fine now (for now being the point of concern). Makes no sense to me whatsoever. I just hope it stays working.
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savetheorcasAuthor Commented:
Was unable to find a solution to my problem, despite trying very hard. This must have been one of those rare (I'm hoping) things that just happens sometimes. As I posted in the comments, I was able to fix this problem by reinstalling Windows. Not an ideal fix, but it worked.
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ITC-TexasCommented:
I am experiencing the same issue, with the exception that the user is opening two mailboxes on the same server. The problem came from nowhere and is driving us nuts. We deleted the OST files for both and allowed them to rebuild and the problem remains. Does anyone have any other suggestions?
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