Outlook 2010 Not sending emails

I have 3 POP/SMTP accounts and 1 MAPI (hotmail) account configured. The last couple of days they are presenting problems because they will not allow me to send an email. I have tried sending one email from any one of the three to the other, or any other recipient and the error is this:

"Your message did not reach some or all of the intended recipients.

Subject: test
Sent: 2/7/2014 5:30 PM

The following recipient(s) cannot be reached:

() on 2/7/2014 5:30 PM
None of your e-mail accounts could send to this recipient."


Now the weird thing, this error message gets sent to the hotmail (MAPI)address almost immediately, which by my understanding, has nothing at all to do with the SMTP accounts. These accounts receive fine. Several resets, malware/virus scans no problems indicated.

I did notice that the TO: email address gets changed to "()"

Any suggestions, I am dead in the water

HammerHead said:

Here is where to start:

Click on file
Account Settings
EMail

Select a pop account to start with. With account selected click on repair. Follow the menus through and it will try to connect and send a test mail. When it fails you will have some idea of the problem. Or you may straighten it out by this method.

MS mail seems to work as expected. As I am troubleshooting further, I notice that when I hit contacts and use the auto fill in for the email address, it gets changed to a "()" upon send. Of course anything addressed to: () will result in an error. However if I manually type in the address, it will go thru. Don't know how all of a sudden this has changed.

Another problem that popped up is that outlook is constantly showing "off line" I cannot turn it online, (mail envelope with red X) however it seems to work ok. And also since I have an option to send email immediately, and it is checked, I have to manually do a send/receive to get it out of my draft folder and on its way.

On the send receive tab, I tried several times to toggle that icon. Persistence and several hours later, toggle worked! I read several instructions on how to do it on the internet, but it would just not cooperate. Day 2 now, it says I am still on line:) Tx for your help

HammerHead said:

How about the repair with the installation disc?

Here is a neat way to do the repair.
Click on Control Panel select Programs and Features. Scroll down to Microsoft Office 2010 and right click on it. Select change. You should get a menu where you can do a repair.

I did as you advised and so far so good. Will give it a couple of days and post back. I also tried yesterday, a new profile for outlook, had to configure the emails etc.

The only remaining "problem" that I now have is that outlook added a great number of folders such as Calendars, notes, journal, Rss Feeds, Suggested Contacts,tasks etc to every email I have configured. (4 email accounts) Normally you should be able to select them and delete, however on mine, the delete button is greyed out. I sure would like to just have the standard ones there, inbox, drafts, sent items, deleted items, outbox etc. Tx for your response!!