I have:
Outlook.com account with 1 alias (I didn't come from hotmail) 
Apple Mail desktop client.
iPhone
 
In the past my desktop mail client allowed me to check mail individually from different addresses from gmail, yahoo, etc. and reply from that same address via a drop down menu.  I'm guessing because of the structure of an alias vs. linked accounts though this has not been the case for outlook.com.

When I select to send from my alias address in the desktop mail client it sends and shows that it sends from the alias address.  But when I go to outlook.com and check it actually never sends from my alias address as it should, but it sends from my primary address.  It's really confusing for customer service people who have multiple cases open for me because of the different email addresses showing up.

Would someone be able to provide a workaround for this?  Right now the alias setup vs. the linked account setup is becoming more of a pain to work with my desktop client and my phone.

Thanks a ton for your help!

I recently set up my mail service for my custom domain through domains.live.com. After configuring the account and sending some test emails through the outlook.com website, I attempted to configure the account through an email program on my computer. I am using the recommended settings for the client and am able to properly send emails but when I go to receive them, I am getting an error message about my password not being received by the pop server: "Sending of password did not succeed. Mail server pop3.live.com responded: POP3 server failed to process your request." I am assuming this is due to some bad configuration on my part with the pop server - be it my username or password.

 

The configuration details I am using are below:

 

Incoming settings:

username: *** Email address is removed for privacy *** (username I use to access outlook.com)

password: (password I use to log into outlook.com)

pop3 server: pop3.live.com

port: 995

security type: SSL/TLS

Authentication: Normal Password

 

Outgoing Settings:

SMTP Server: smtp.live.com

Port: 587

Security Type: STARTTLS

Authentication: Normal Password

 

Again, I can send email properly through both the web client as well as the desktop client I am using. However, I am only able to receive mail through the web client. 

 

Is it an issue with the custom domain or something else?

 

 

Thanks,

Jeff