Outlook 2010 Sending To Wrong Account

Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#1
I have an Outlook 2010 on a Win 7 (32) Laptop that has two IMap accounts and one Exchange account (HTTP) and when I try to send a message using an IMAP account, Outlook refuses my direction and starts sending to the Exchange Server. Only when I select the Exchange account as the source of the message will the send be successful. BTW, the Exchange account is last in priority in the profile, one of the IMAP accounts being specified as default.

I've tried registry hacks that attempt to force manual selection of the sender but they don't work for me. In effect, it would seem that Outlook is trying to use the Exchange Server as an open-relay server but I can't really prove that. Still, RackSpace doesn't seem to tolerate such nonsense. (Good for them)

Is there a solution for my problem? I really don't care for the GUI of Outlook 2013 or 2016 although I suppose I could force myself to use one of them if they'd solve my problem.

Need some advice here, please...
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#3
Yes, it does. I don't know if reinstalling 2010 would fix the issue. I've "repaired" it to no avail.
The PSTs and OSTs are unique to each account. I intuit that I'd have to completely expunge
the Office information from the registry to make re-installation a worthwhile project.
But I'm not on intimate terms with Office so I really don't know.
Thanks for your reply....
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#4
I don't know if reinstalling 2010 would fix the issue.
I doubt it. I'd make a second profile and see if it works as expected in the new profile first.

Can you add a pst file to the profile and set it as default then see if it works?

I'll try to repro it on my test system this evening.
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#5
I did create a new profile, removed the old one, re-created the accounts. I even went to the file storage areas in the APPDATA area and removed the old PST and OST files, plus anything else that looked "outlook".
(FWIW, the Exchange Account is an "autodiscover" account. I don't know if that matters.)
Same problem.
What I'm forced to do when replying/sending to one if the IMAP accounts is use the host's webmail interface.
Except for receiving mail, it's almost as if I don't have Outlook at all.
I've never seen this kind of behavior before...
 
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#6
Did you see if it also happens in Safe mode? To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.

Are you using any addins?

It's definitely not correct behavior - especially for replies.
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#7
Sorry I'm so tardy responding to you Diane. No, I have not yet tried safe mode. I have built new profiles -- in fact, I've deleted all profiles and started from scratch, all to no avail. I'd not want you to spend a bunch of time on this Diane. My new laptop is to be delivered in two (2) days and I'll start over on Windows 10 Pro with Office 2010 Pro and hope for the best...
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#8
My new laptop is to be delivered in two (2) days and I'll start over on Windows 10 Pro with Office 2010 Pro and hope for the best...
The laptop will probably have the new Windows store version installed. Go to Settings, Apps & Features to uninstall the Microsoft Office Desktop apps before installing Office 2010.
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#9
The laptop will probably have the new Windows store version installed. Go to Settings, Apps & Features to uninstall the Microsoft Office Desktop apps before installing Office 2010.
Yes, it's an OEM Windows 10 (via DELL) and it was 'way behind in updates. No HUHU. I'll test office 2010 once I get it up and running.
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#10
Diane, I haven't tested this outside of my own lab, but it appears to be working properly. At least the proper SENT items are in the proper folders.
There was ONE anomaly though: I was unable to add the RackSpace Exchange account to a profile with IMAP accounts in it. I had to remove all the IMAP accounts and then add the autodetect Exchange account -- which worked! THEN, I was able to add the two IMAP accounts back to the profile and all seems to be well.

There were a "ton" of updates since SP1 and they were handled expeditiously. I didn't try creating a profile until all the updates were in.
If I continue to have trouble with this, I guess I'll cave in and install either 2013 or 2016. I don't care for either of them but when all else fails...
Thanks for looking into this with me.
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#11
Diane, with Outlook 2010 configured with the RackSpace Exchange account, and two IMAP accounts (1 from Earthlink and 1 from GMAIL), Outlook refuses to connect to the Exchange account. It throws up a username/password screen as if the account has the wrong password on it. It doesn't.

However, it works IFF the Exchange Account is the DEFAULT account! That's not what I'd like but I can live with it.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#12
There was ONE anomaly though: I was unable to add the RackSpace Exchange account to a profile with IMAP accounts in it. I had to remove all the IMAP accounts and then add the autodetect Exchange account -- which worked! THEN, I was able to add the two IMAP accounts back to the profile and all seems to be well.
I had another client who has problems similar to this. I can't recall which outlook they used though.

If I continue to have trouble with this, I guess I'll cave in and install either 2013 or 2016. I don't care for either of them but when all else fails...
Thanks for looking into this with me.
While the act of upgrading might fix it, it should work with your cuirrent version. 2013 will be hard to find these days and if you are getting the perpetual version, i'd wait for 2019's release - just because it gives you a couple more years of life.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#13
Diane, with Outlook 2010 configured with the RackSpace Exchange account, and two IMAP accounts (1 from Earthlink and 1 from GMAIL), Outlook refuses to connect to the Exchange account. It throws up a username/password screen as if the account has the wrong password on it. It doesn't.

However, it works IFF the Exchange Account is the DEFAULT account! That's not what I'd like but I can live with it.
Exchange likes to be the default data file but should work ok with any account as default email.

Do you know what version of exchange you have at rackspace?
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#14
Exchange likes to be the default data file but should work ok with any account as default email.

Do you know what version of exchange you have at rackspace?
I'm not sure but I strongly suspect it's 2016. I never thought of Exchange as the culprit but we've both seen issues with that beast... :)
The behavior was really odd though.

I routinely set up Email accounts using the MAIL applet in ControlPanel! And when I set up the exchange account after having setup the IMAP accounts, it appeared that all was well. It was only after Outlook was started up that it failed to connect to the account and kept hounding me with the Username/Password pop-up. Going back to the MAIL applet, I was again hounded by the Username/Password pop-up until it was clear I wasn't trying to connect to the account.

I can get 2013 and 2016 - no problems there.
Have a good evening.
 
Outlook version
Outlook 2010 32 bit
Email Account
IMAP
#15
Diane, I'm truly embarrassed by this but it seems AT&T blocks Port 25 to non AT&T domains.
I found an alternate port (587) that works.
Problem solved.
I can't tell you how long it's been since I've seen a port 25 blocker in operation. :(
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
#16
Diane, I'm truly embarrassed by this but it seems AT&T blocks Port 25 to non AT&T domains.
I found an alternate port (587) that works.
Don't be embarrassed - you've educated me and now when someone has a problem, I'll know the answer. :)
 
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