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 email@example.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 firstname.lastname@example.org, the message will not be sent. However, (usually) if I close Outlook and re-launch it, the email@example.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 firstname.lastname@example.org 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.