Mail cannot connect to SMTP for Hotmail/Live/Outlook.com
I cannot believe how many people are having variations of this problem. On the Outlook.com discussion forum there seemed to be a few "private" responses from moderators but I am not sure why answers have not been made public.
It suits me not to use a browser to check my Hotmail. Up until recently I had no difficulty using the Mail application on an iMac to check my Hotmail email using POP with the settings Incoming Mail Server: pop3.live.com and Outgoing Mail Server (SMTP): smtp.live.com:myname@hotmail.com. Recently I have had problems and in particular keep getting in the Mail Connection Doctor the error message "Could not connect to this SMTP".
In Outlook.com Help there is information on setting up apps with POP3 and SMTP. Following those instructions I tried using the settings Incoming Mail Server: pop-mail.outlook.com and Outgoing Mail Server (SMTP): smtp-mail.outlook.com This did not seem to work so I tried: smtp-mail.outlook.com:myname@hotmail.com but still get the error message "Could not connect to this SMTP".
Mail on the iMac lets you click on Edit SMTP Server List which opens a dialogue box to select Advanced > Authentication > Password and entered username & password. This didn't stop the error message though.
With POP the problem seems only to be with the Outgoing Mail Server (SMTP) and not the Incoming Mail Server. So with this server arrangement I could get mail but not send it.
Interesting, when I try to add a new email account in Mail on the iMac it finds Hotmail IMAP automatically. This is even though I have POP enabled in my settings options in Outlook.com.
Looking at the various discussions I cannot find an answer to how to now check my Hotmail using POP with the Mail application on my iMac?
Does Outlook.com still support the Mail application on the iMac using POP for Hotmail accounts?
Does Outlook.com only support the Mail application on the iMac using IMAP for Hotmail accounts?
Is the problem an SSL certificate issue? I note in an answer by Lanie P (Microsoft Forum Moderator) on 27 Jan 2014 she said "Hi Everyone, Apologies for the delayed response. As an update regarding this case unable or having a hard time connecting your account to SMTP server, our Product Group verified that there is an SSL certificate issue on our end and they are still on process creating a fix about it. But the time frame is not definite. Our Microsoft Engineers advised that this will get fixed in their future release. We would like to ask for your patience regarding this matter. Thanks!" If this is the situation, has it been fixed?
A couple of disussions suggested specifying a particular port number eg 25 but that did not seem to work.
There is the following discussion about a similar problem which identified the router as the problem but I haven't changed my router or service provider for ages.
Hotmail smtp.live.com server will not connect
25479 Views 42 Replies Latest reply: Jan 24, 2014 7:30 AM by wembley2014 
Level 1 (0 points)
Help from anyone would be great. I have had my Hotmail email address for ages and would like to continue to use it for non-work things. I suppose I could easily change to another email provider. Particularly, with the iMac I already have an iCloud account.
Thanks
iMac (21.5-inch Mid 2010), Mac OS X (10.6.8), Also older Macs