Cannot send mail (SMTP offline)

I have posted the correct settings for Hotmail SMTP below, enter these settings exactly as posted (except for username and password)

• Windows Live Hotmail SMTP server address: smtp.live.com
• Windows Live Hotmail SMTP user name: Your complete Windows Live Hotmail email address ("me@hotmail.com" or "me@live.com" for instance)
• Windows Live Hotmail SMTP password: Your Windows Live Hotmail password
• Windows Live Hotmail SMTP port: 587
• Windows Live Hotmail SMTP TLS/SSL required: yes

I can not help without more information regarding the other account.

Time to contact Microsoft.

Hi Axiomatic48

I am in the UK and eventually found the problem was due to my BT Home Hub Router. Not sure where you live, but of you are in the UK, this might work for you.

I found this fix below on https://discussions.apple.com/thread/4604180?start=15&tstart=0

It worked for me. If you can't link to the URL, here is the body of the text

There's an issue related to the BT homehub that is providing a hostname that is "syntactically incorrect" for several smtp server.

Here's how you can fix it.

Using your internet browser, go to the address "192.168.1.254

- Follow instructions to reset your password if asked.

- Then go to "Settings", then "Advanced Settings" and "home network"

You will see there all the devices that are connected or that has been connected before. It's gonna be easyer if yout computer is the only one connected.

Your computer should have a name like "unknown-xx:xx:xx:xx:xx ...

Click on this name, chose another name without any special characters, like "macbook" for exemple.

And then click on "apply"

- restart your computer.

That should fix the issue.

Credit goes to vincentfromcork for providing me with the solution.

If this works for you, spread the word :-)

Interesting, and thank you Cornish_techie - I will try this fix today if I can.

The computer-nervous friend I have who is suffering this problem (I am using BT as an ISP and Google Mail on my Mac, and everything has always "just worked" for me) switched about a week ago from Windows XP to an iMac (with the latest Mountain Lion OS X), but had been using (the latest) Thunderbird mail client set up for Hotmail/Outlook (POP and SMTP) on Windows XP without any problem. When I switched him over to Apple Mail (similarly set up), mail sending (via SMTP) didn't work, which problem is the original subject of this thread. (I've not looked at his BT Home Hub 3 settings at all so far.)

When the fault occurred, and I read some of the earlier postings in this thread, my first thought was that the problem was perhaps the apostrophe that OS X places in its 'computer name' - e.g. "John Smith's iMac" - set under 'System Preferences' -> 'Sharing'. However, taking the apostrophe out and restarting OS X didn't fix mail sending by SMTP to Hotmail/Outlook (smtp.live.com). When I login to the 'Advanced Settings' section of my own BT Home Hub 3, I see that the 'Home network name' for my Mac there is the name of my OS X install, but with the apostrophe automatically removed and one or more hyphens added - e.g. "john-smiths-imac" - the MAC address is shown under this name in the list of devices, but the 'Home network name' field itself doesn't contain the MAC address with its possibly SMTP-upsetting colons.

So you're saying that its the hyphen or hyphens that Hotmail/Outlook SMTP is not coping with? (Just alphabetic - alphanumeric? - characters are ok, I read.) I'll try the fix today if I can, and post to say whether it cures my friend's problem or not.

Yes, remove the hyphens and the Hotmail problem is fixed. The hyphens are not a problem with GMail or Yahoo! (BT) mail sending.

Jamurdie - You are a STAR 🙂

I had encountered the SMTP issue several times, deleted .plist, deleted accounts, keychain prefs, even tried a different mail client - Albeit intermittently, and that was the biggest issue, it was intermittent - it never went away and last week my mail went down for good -

Frustrated beyond belief, and during a lunch break, I came across your post about the BT3 home hub -

Luckily I had an old BT2 home hub, and it came to my mind these problems only started after wee took delivery of a new BT3 home hub, so I unplugged that, put back the BT2 home hub in and hey presto - issue resolved......

I cannot say how much time and effort I wasted on this small issue - something in the region of 60-80 man hours

Thank you so much -

Hi, pronimen - glad you, too, have fixed this problem for yourself. My friend's BT-connected iMac continues to function correctly with Hotmail/Outlook e-mail. Thank you for your thanks! (I know how frustrating it is to have to try and retry many alleged fixes until I find one that works.) If you login to your BT Home Hub 3 and remove the hyphens from the domain name Hotmail/Outlook e-mail will work just fine, as explained above. (Mind you, my BT Home Hub 3 gives me problems with my 1st generation Apple TV which I've not yet fixed, but that's another story.)

I think, though, that you should give Cornish_techie the recognition for having solved this problem - his/hers was the first accurate offered solution I found here - and, Axiomatic48 (as the original author of this thread), if you're reading this, why not give Cornish_techie their 'This fixed my problem' points. We need to encourage people to stay around here to offer solutions for problems beyond Apple's control.

Opps, I did not intentionally mean to miss anyone out. Jamurdie, you are indeed right -

Thank you to Cornish_techie, Axiomatic48, and anyone else who takes the time and effort to work out and post solutions.

Just to further add - Prior to this solution coming, my brand new retina had been to an Apple genius bar twice, only to be told, "nothing wrong, no-one else has this issue". I then contacted my ISP, who were excellent, yet could not resolve the issue......

With my e-mail down for day's going into weeks, I cannot explain the frustration I felt - Thanks to this post, but more importantly, thanks to all you guys who take the time and effort to SHARE your solutions - without it, my tiny one man business would still be down.

I am still overwhelmed to find out it was BT's home hub (BT3), as this was never an area I would have considered in a million years -

There are some great people in our world 🙂

Thank you guys.....

off to do some mails now ........................

Cornish,

Ive had this problem for a year now and been through all the same fixes mentioned in all other posts. I have now changed the name of my device and have email back. How simple was that. For me very, for thoses that worked it out, wow. Amazing work well done.

Just spent another 5 mind crushing days with a dropped out SMTP error AGAIN !!!!

BT said it was my webhost

Webhost said it was BT's hardware problem

Bla, bla, bla

Change BT Hub to older hub2 (worked for month then poof) GONE AGAIN!

Performed all the usual fixes', i.e. deleted .plist, mail accounts, and checked the details a thousand times..... still did not work.

Eventually, and I mean eventually it popped on live the same way it went down - without notice - though I believe it was a 50/50 BT/Web-Host issue as I've heard (though cannot confirm) that BT Hubs (and that's all of them) are made by Huawei (china) which come pre installed with inherent issues..... This makes sense as living and working in China for 10 years, they do have the same issues as we are experiencing here, but they are not called BT in China, it's called normal hub issues.......

Having said all the above, this would be plausible if the issue was restricted to the UK, yet as I see it, it's the US as well, so my theory is most likely just a theory....

So while it's working and functional today - It's by no means a guaranteed fix, and yes it's still driving me crazy......

For what difference it will make, I have taken the above advice and changed the device name 🙂

Thanks jarmurdie, worked for me! 🙂

This worked a treat for me 🙂 Thank you Cornish_techie!