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Level 1

8 points

The connection doctor, shows that smtp.live.com is not connecting?

Hi,

Im having the exact same problem, email has worked fine since 2008 and on friday it stopped allowing me to send email. I have no problem recieving, or sending from my iphone over the same newtwork my mac is using.

The smtp.live.com server is showing as offline, having tried changing ports, deleting and reinstalling my account.

I no longer have tech support from apple, and have reached the point I no longer have any idea what to try in order to resolve this issue.

Im based in the UK, using snow leopard on a 2008 machine and my service is provided through BT infinity.

Any help would be greatly appreciated.

Regards

Phil

MacBook Pro, Mac OS X (10.6.8)

Posted on Nov 27, 2012 2:17 AM

33 replies

Nov 28, 2012 2:38 AM in response to Untzy

OK, try in Terminal

telnet 65.55.162.200 25

and see what happens.

Untzy Author

Level 1

8 points

Nov 28, 2012 5:13 AM in response to Austin Kinsella1

That reults in this message,

Trying 65.55.162.200...

Connected to 65.55.162.200.

Escape character is '^]'.

220 BLU0-SMTP133.blu0.hotmail.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Wed, 28 Nov 2012 05:12:49 -0800

Nov 28, 2012 10:00 AM in response to Untzy

So you can also connect with telnet to the live.com server that your DNS finds. What version of Mail have you?

Untzy Author

Level 1

8 points

Nov 28, 2012 10:10 AM in response to Austin Kinsella1

it's Version 4.6 (1085)

Untzy Author

Level 1

8 points

Nov 29, 2012 12:07 AM in response to Untzy

I tried updating the software, its now running Version 6.2 (1499)

This has had no affect on the smtp issue.

Nov 29, 2012 4:20 AM in response to Untzy

What software did you update?

Untzy Author

Level 1

8 points

Nov 29, 2012 4:40 AM in response to Austin Kinsella1

OSX, now running lion.

its made no difference.

Nov 30, 2012 1:43 PM in response to Untzy

I have exactly the same problem, followed the steps above and no joy! Running 10.7.5, can receive mail but not send. I can send mail fine from various devices connected to the same router via BT infinity but not from my Mac. So I'm pretty certain its a problem with Mac mail as I've eliminated everything else. So annoying, had a good search of the forums and can't see any solutions.

Untzy Author

Level 1

8 points

Nov 30, 2012 2:16 PM in response to sjallam2012

Tried using the connection doctor within mac mail to see if it showed any obvious issue, which reslted in the following,

WROTE Nov 30 09:13:27.208 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x7fe9a2bd9300 -- thread:0x7fe9a26c6f90

HELO unknown-00:23:12:54:23:79.home

READ Nov 30 09:13:27.305 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x7fe9a2bd9300 -- thread:0x7fe9a26c6f90

501 5.5.4 Invalid Address

Tried googling the results but nothing that helps so far.

Untzy Author

Level 1

8 points

Dec 1, 2012 9:57 AM in response to Untzy

Anyone?

Dec 1, 2012 8:04 PM in response to Untzy

I hope I can join the fun. Having a very similar issue. Running 10.8.2 and Mail 6.1 (1499). This is on a new Mac mini that I just set up. Was running Snow Leopard - had the mail issue. Upgraded to Mountain Lion. Still have the isse.

I get the "p01..." port 143" message for connecting to servers. I am connected to internet. Mail accout on iphone, ipad, Mac Air working fine.

However - I can send an email from the Mac Mini. I just cannot see any mailboxes other that In, Sent, Trash

Any suggestions would be greatly appreciated

Dec 2, 2012 3:40 AM in response to Untzy

Ok, this is getting weirder. I can now send from my macbook via wifi on any connection including my BT Infinity router on my private network as well as BT fon etc. But I cannot send when I connect my cable to my Macbook. It get the smtp error we all appear to have. So this is increasingly looking like something weird with the BT infinity router. Baffled.

Dec 2, 2012 5:02 AM in response to Untzy

I would like to look at this at the packet level, to see if I can work out what is, or is not, happening. If you don't mind, quit any program using the internet (to keep it simple) except Mail. In Terminal, give the command

sudo tcpdump -i en1 -s 0 -B 524288 -c 100 -w ~/Desktop/DumpFile01.pcap

(Simplest is probably to copy and paste it) It will prompt you for your admin password.

then in Mail get mail then try sending an email - have one ready to send before giving the Terminal command. You can restart Safari or whatever. When the Terminal command finishes - it will put up messages something like

100 packets captured

226 packets received by filter

0 packets dropped by kernel

email to me (my address is in my profile) the Desktop file DumpFile01.pcap. (Warning: it may have plaintext passwords in it. I won't attempt to use them, and will delete the file after reading it)

Dec 2, 2012 9:37 AM in response to Untzy

Emailed you, not sure its correct.

Untzy Author

Level 1

8 points

Dec 3, 2012 8:14 AM in response to sjallam2012

Ok managed to fix it, try the following.

1. Login to your BT home hub manager (this can be done using the router address located at: system preferences/network/advanced/TCP/IP)

2. Input your router address into the web browser search bar

3. Once on the access page you will need to input your wireless admin password (found on the back of your router)

4. When you are on the home page, you will need to follow the following steps to change your device name:

5. Select "A-Z" in the top right section of the page

6. Click on "Home Network" from the available list of options

7. Click on the Device in question (it should be showing as connected - I identified mine by the mac address, although it was named as 'unknown')

8. Under Device Information, enter a new name (be sure this is memorable in case you need it again)

9. Ensure Always use this address is set to Yes (it is by default)

10. Click Apply.

You will then need to restart your computer - after this, hopefully the problem will be resolved....

The connection doctor, shows that smtp.live.com is not connecting?