I don't use MS Outlook at all. I think that because it is Microsoft, it is extremely vulnerable to viruses, hackers, bots and spammers. It is an easy gateway for malware and everything bad about the internet. It hasn't even been configured on my machine.
However, I am writing a program for inviting people to our app, and I needed to get Outlook contacts to send them an email (that will be the subject of another blog post). So I configured Outlook and the base email address was an AOL email address that I rarely use except for testing and for signing up for things where I don't want them to know my real identity (like the kajillions of white papers and secrets that one can get just for giving someone your email address -- a spam feedlot of sorts).
Well, it was supposed to be painless and take a few seconds. I let the wizards set up Outlook for me and then of course, I had to test it. I sent an email to my other email address. Immediately it was rejected. The error message was:
Your message did not reach some or all of the intended recipients.
Subject: Test
Sent: 05/05/2014
The following recipient(s) cannot be reached:
'test@test.com' on 05/05/2014 11:19 AM
<test2@aol.com>: Sender address rejected: not owned by user test2
I thought -- WTF!!! It had just used that identity to create an account for me using the account wizard. It had just authenticated me to aol using that identity. It was a total mystery.
I burned over an hour trying to de-bug this. Here is the simple solution. I went to Accounts on Outlook and clicked on the account to show the properties. The username was test2. When I go into the web interface of AOL mail and sign in, I just put in test2 and the password. Outlook knew that the domain was AOL.com because it had just automatically used those exact same credentials to create the account. To make it work, I simply modified the username to include the domain -- ie. instead of test2, I put in test2@AOL.com and it worked.
This has done nothing to change my opinion of Microsoft products. They are still a piece of crap.
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