Mail: SMTP not working on MacBook Air, same settings work on iPhone

Hello. First time posting here so please forgive any indiscretion. I have searched the support forums but have been unable to find an answer to this problem.

I have identical Mail configurations setup on my iPhone 5 (iOS 7.0.4) and my MacBook Air (OS X 10.9.1). I am able to receive email fine on both (POP), and I can send mail (SMTP) from my iPhone, but the *identical* SMTP settings on my Macbook Air will not send email. The error is:

"Could not connect to this SMTP server. Check your network connection and that you entered the correct information in the Account preferences. Also verify that the server supports SSL. If if does not, deselect the "Use SSL" checkbox in the Advanced tab of Account preferences".

The SMTP settings on both the iPhone and Macbook Air are:

- Use custom port 465 (I have also tried 'Use default ports')

- Use SSL (I have also tried without)

- Authentication is password (I've confirmed user/password is correct)

In my testing I setup a POP/SMTP account on another computer (not a Mac) using Outlook and everything works fine there as well. So from what I can tell this is specific to Mail on my Macbook Air only.

I read in this forum that some users have installed Outlook on their Macbooks and had success. So this seems specific to Mail on Macbook Air?

Any assitance would be much appreciated! Thank you!

Mail-OTHER, OS X Mavericks (10.9.1)

Posted on Jan 8, 2014 8:04 AM

18 replies

Oct 27, 2014 8:59 AM in response to scrappleandeggs

Just following up this many months later that I have not been able to determine the problem. Again, for what its worth, in a nutshell:

> The Identical SMTP settings in Mail which work on my iOS devices (one iPhone and one iPad) do not work on my Macbook Air. The error in Connection Doctor is constantly "Could Not Connect to this SMTP server". I have tried every possible combination of settings.

I have been waiting for the Yosemite release to see if the new Mail would fix this problem (which seemed to start with Mavericks release), but the behavior is the same. Sigh..

Oct 28, 2014 5:49 AM in response to scrappleandeggs

One more bit of information - iPhoto is sending mail a-ok from my laptop using the same email account that is not sending via Mail. How is that possible? Does iPhoto use a different method or authentication to send mail?

blueeos

Level 1

87 points

Feb 25, 2015 4:11 PM in response to scrappleandeggs

I too am unable to send email from my MBA (Yosemite) in either hotmail.com or msn.com or outlook.com. While I can't be certain, I think the trouble started in Dec '14 and continues to this day. I can and do receive daily mail in hotmail.com, msn.com and outlook.com, but if I reply to any of these message or try to send a new message, I have to select gmail.com as my outbound server. I do seem to be able to send mail with these same accounts with my iPhone 6.

If I go into settings on my MBA, I see the following...

IMAP Hostname imap-mail.outlook.com

IMAP Path Prefix (blank)

Port: 993 Use SSL (checked)

I've played around with this numbers to no avail. I think my trouble started when I added an Outlook account. I'm wondering if I should have used another template from the list that starts with iCloud, E Exchange, etc, etc. I went with "Add Other Account". I"m thinking of dumping ALL my MS mail accounts and switching to Gmail, but so many of my friends and financial sites have my MS Hotmail or MSN.

I've searched google for a MS site that might help me, but so far I haven't found a helpful site and I've already spent WAY too many hours trying to fix this.

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Mail: SMTP not working on MacBook Air, same settings work on iPhone