I can't send hotmail emails from my mac but I can receive them

The Internet standards for protocols mandate that component hostname labels may contain only the ASCII letters 'a' through 'z' (in a case-insensitive manner), the digits '0' through '9', and the hyphen ('-').

So, spaces are invalid just like ":"

Hi Vincent,

I seem to be the only one this fix hasn't worked for.

I have a Hotmail account which hasn't sent an email for a year now through the mail app on my Mac.

Similar story to everyone else. keeps saying the smpt server is offline... I've been through the thorough diagnostics with Apple to no avail. I got a refund as they couldn't help me.

I recently added a gmail account and it worked fine.

You seem to be the guy to talk to as I am getting no help from anywhere at all.

Many thanks

An extremely frustrated Mac user

One year without senging email is tough !

It's hard to believe that the Apple support couldn't find how to fix your issue. Makes me think that maybe it's something wrong with you account. But I don't have enough informations to help you here.

In this situation, the "show more details" of the connection doctor window can be realy helpful. If you don't mind posting it.

TrickyRicky1987 wrote:

Hi Vincent,

I seem to be the only one this fix hasn't worked for.

I have a Hotmail account which hasn't sent an email for a year now through the mail app on my Mac.

Post the settings you are using for the Hotmail SMTP server.

Post them here.

It's never been green before but it's still not sending

I've copied what came up along with a screen shot of what happens

INITIATING CONNECTION Apr 05 16:14:03.868 [kCFStreamSocketSecurityLevelNone] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

CONNECTED Apr 05 16:14:04.836 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

READ Apr 05 16:14:04.936 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

+OK BLU0-POP566 POP3 server ready

WROTE Apr 05 16:14:04.936 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

CAPA

READ Apr 05 16:14:05.033 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

-ERR unrecognized command

WROTE Apr 05 16:14:05.035 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

USER rmk1234@hotmail.com

READ Apr 05 16:14:05.132 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

+OK password required

WROTE Apr 05 16:14:05.132 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x608000e6dfc0

PASS ************

READ Apr 05 16:14:05.947 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

+OK mailbox has 73 messages

WROTE Apr 05 16:14:05.947 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

STAT

READ Apr 05 16:14:06.044 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

+OK 73 2210039

WROTE Apr 05 16:14:06.045 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

UIDL 1

READ Apr 05 16:14:06.144 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

+OK 1 7910A358-B489-11E3-99A6-00237DE4A74A

WROTE Apr 05 16:14:06.144 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

UIDL 73

READ Apr 05 16:14:06.241 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

+OK 73 A370A9A1-BCD2-11E3-9C36-D89D675C7980

WROTE Apr 05 16:14:06.242 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

QUIT

READ Apr 05 16:14:06.339 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000002df330 -- thread:0x60000046c640

+OK mailbox unchanged, POP3 server signing off

INITIATING CONNECTION Apr 05 16:18:46.978 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000e67dc0

CONNECTED Apr 05 16:18:47.544 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

READ Apr 05 16:18:47.647 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

220 BLU0-SMTP309.phx.gbl Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Sat, 5 Apr 2014 08:18:47 -0700

WROTE Apr 05 16:18:47.660 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

EHLO mac.home

READ Apr 05 16:18:47.766 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

250-BLU0-SMTP309.phx.gbl Hello [86.176.234.51]

250-TURN

250-SIZE 41943040

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-TLS

250-STARTTLS

250 OK

WROTE Apr 05 16:18:47.766 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

STARTTLS

READ Apr 05 16:18:47.880 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

220 2.0.0 SMTP server ready

WROTE Apr 05 16:18:48.367 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

EHLO mac.home

READ Apr 05 16:18:48.473 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

250-BLU0-SMTP309.phx.gbl Hello [86.176.234.51]

250-TURN

250-SIZE 41943040

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-AUTH LOGIN PLAIN XOAUTH2

250 OK

WROTE Apr 05 16:18:48.476 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

AUTH PLAIN (*** 72 bytes hidden ***)

READ Apr 05 16:18:49.061 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

235 2.7.0 Authentication succeeded

WROTE Apr 05 16:18:49.061 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

MAIL FROM:<rmk1234hotmail.com>

READ Apr 05 16:18:49.167 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

501 5.5.4 Invalid Email address

WROTE Apr 05 16:18:49.167 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6080004d4820 -- thread:0x608000c7e740

QUIT

INITIATING CONNECTION Apr 05 16:19:16.197 [kCFStreamSocketSecurityLevelNone] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x608001071d80

CONNECTED Apr 05 16:19:17.314 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x608001071d80

READ Apr 05 16:19:17.414 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK BLU0-POP435 POP3 server ready

WROTE Apr 05 16:19:17.414 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

CAPA

READ Apr 05 16:19:17.520 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

-ERR unrecognized command

WROTE Apr 05 16:19:17.522 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

USER rmk1234@hotmail.com

READ Apr 05 16:19:17.625 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK password required

WROTE Apr 05 16:19:17.625 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

PASS ************

READ Apr 05 16:19:18.460 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK mailbox has 73 messages

WROTE Apr 05 16:19:18.460 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

STAT

READ Apr 05 16:19:18.563 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK 73 2210039

WROTE Apr 05 16:19:18.566 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

UIDL 1

READ Apr 05 16:19:18.667 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK 1 7910A358-B489-11E3-99A6-00237DE4A74A

WROTE Apr 05 16:19:18.667 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

UIDL 73

READ Apr 05 16:19:18.771 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK 73 A370A9A1-BCD2-11E3-9C36-D89D675C7980

WROTE Apr 05 16:19:18.772 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

QUIT

READ Apr 05 16:19:18.875 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6080004d36a0 -- thread:0x60000106e980

+OK mailbox unchanged, POP3 server signing off

INITIATING CONNECTION Apr 05 16:21:45.130 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x60000107ae40

CONNECTED Apr 05 16:21:45.825 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x60000107ae40

READ Apr 05 16:21:45.928 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x60000107ae40

220 BLU0-SMTP20.phx.gbl Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Sat, 5 Apr 2014 08:21:45 -0700

WROTE Apr 05 16:21:45.938 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x60000107ae40

EHLO mac.home

READ Apr 05 16:21:46.042 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

250-BLU0-SMTP20.phx.gbl Hello [86.176.234.51]

250-TURN

250-SIZE 41943040

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-TLS

250-STARTTLS

250 OK

WROTE Apr 05 16:21:46.042 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

STARTTLS

READ Apr 05 16:21:46.164 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x60000107ae40

220 2.0.0 SMTP server ready

WROTE Apr 05 16:21:46.678 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

EHLO mac.home

READ Apr 05 16:21:46.783 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

250-BLU0-SMTP20.phx.gbl Hello [86.176.234.51]

250-TURN

250-SIZE 41943040

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-AUTH LOGIN PLAIN XOAUTH2

250 OK

WROTE Apr 05 16:21:46.786 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

AUTH PLAIN (*** 72 bytes hidden ***)

READ Apr 05 16:21:47.336 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

235 2.7.0 Authentication succeeded

WROTE Apr 05 16:21:47.337 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

MAIL FROM:<rmk1234hotmail.com>

READ Apr 05 16:21:47.442 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

501 5.5.4 Invalid Email address

WROTE Apr 05 16:21:47.442 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

QUIT

INITIATING CONNECTION Apr 05 16:22:35.715 host:pop3.live.com -- port:995 -- socket:0x0 -- thread:0x608001270200

INITIATING CONNECTION Apr 05 16:22:35.715 host:smtp.gmail.com -- port:587 -- socket:0x0 -- thread:0x608001270200

INITIATING CONNECTION Apr 05 16:22:35.716 [kCFStreamSocketSecurityLevelNone] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001270200

INITIATING CONNECTION Apr 05 16:22:35.716 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608001270200

CONNECTED Apr 05 16:22:36.703 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x608001270000

CONNECTED Apr 05 16:22:36.733 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001270200

READ Apr 05 16:22:36.733 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001270200

* OK Gimap ready for requests from 86.176.234.51 l51mb28861345weo

WROTE Apr 05 16:22:36.733 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001270200

1.127 CAPABILITY

CONNECTED Apr 05 16:22:36.734 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608001270200

READ Apr 05 16:22:36.763 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x600001074d40

* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH AUTH=XOAUTH2 AUTH=PLAIN AUTH=PLAIN-CLIENTTOKEN

1.127 OK Thats all she wrote! l51mb28861345weo

WROTE Apr 05 16:22:36.764 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001270200

2.127 ID ("name" "Mac OS X Mail" "version" "7.2 (1874)" "os" "Mac OS X" "os-version" "10.9.2 (13C64)" "vendor" "Apple Inc.")

READ Apr 05 16:22:36.795 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x600001074d40

* ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "86.176.234.51" "connection-token" "l51mb28861345weo")

2.127 OK Success l51mb28861345weo

READ Apr 05 16:22:36.803 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x600000c7c640

+OK BLU0-POP763 POP3 server ready

WROTE Apr 05 16:22:36.803 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x600000c7c640

CAPA

WROTE Apr 05 16:22:36.811 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001077580

3.127 AUTHENTICATE PLAIN-CLIENTTOKEN (*** 132 bytes hidden ***)

READ Apr 05 16:22:36.836 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608001060980

220 BLU0-SMTP168.phx.gbl Microsoft ESMTP MAIL Service, Version: 6.0.3790.4675 ready at Sat, 5 Apr 2014 08:22:36 -0700

CONNECTED Apr 05 16:22:36.843 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x600000c7c640

WROTE Apr 05 16:22:36.856 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608001060980

EHLO mac.home

READ Apr 05 16:22:36.867 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

220 mx.google.com ESMTP h8sm11427764wiz.12 - gsmtp

WROTE Apr 05 16:22:36.881 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

EHLO mac.home

READ Apr 05 16:22:36.900 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x608000468240

-ERR unrecognized command

WROTE Apr 05 16:22:36.902 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x608001060980

USER rmk1234@hotmail.com

READ Apr 05 16:22:36.962 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608000468240

250-BLU0-SMTP168.phx.gbl Hello [86.176.234.51]

250-TURN

250-SIZE 41943040

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-TLS

250-STARTTLS

250 OK

WROTE Apr 05 16:22:36.963 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608000468240

STARTTLS

READ Apr 05 16:22:36.987 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

250-mx.google.com at your service, [86.176.234.51]

250-SIZE 35882577

250-8BITMIME

250-STARTTLS

250-ENHANCEDSTATUSCODES

250 CHUNKING

WROTE Apr 05 16:22:36.987 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

STARTTLS

READ Apr 05 16:22:36.999 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x608001060980

+OK password required

WROTE Apr 05 16:22:36.999 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x608001060980

PASS ************

READ Apr 05 16:22:37.031 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

220 2.0.0 Ready to start TLS

READ Apr 05 16:22:37.083 [kCFStreamSocketSecurityLevelNone] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x608001060980

220 2.0.0 SMTP server ready

WROTE Apr 05 16:22:37.193 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608001060980

EHLO mac.home

READ Apr 05 16:22:37.224 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

250-mx.google.com at your service, [86.176.234.51]

250-SIZE 35882577

250-8BITMIME

250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN

250-ENHANCEDSTATUSCODES

250 CHUNKING

WROTE Apr 05 16:22:37.233 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x608000468240

AUTH PLAIN-CLIENTTOKEN (*** 132 bytes hidden ***)

WROTE Apr 05 16:22:37.496 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x600001065a40

EHLO mac.home

READ Apr 05 16:22:37.600 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x600001065a40

250-BLU0-SMTP168.phx.gbl Hello [86.176.234.51]

250-TURN

250-SIZE 41943040

250-ETRN

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-8bitmime

250-BINARYMIME

250-CHUNKING

250-VRFY

250-AUTH LOGIN PLAIN XOAUTH2

250 OK

WROTE Apr 05 16:22:37.602 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x600001065a40

AUTH PLAIN (*** 72 bytes hidden ***)

READ Apr 05 16:22:37.801 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x600001065a40

+OK mailbox has 74 messages

WROTE Apr 05 16:22:37.801 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x600001065a40

QUIT

READ Apr 05 16:22:37.901 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:pop3.live.com -- port:995 -- socket:0x6000004c80a0 -- thread:0x600001065a40

+OK mailbox unchanged, POP3 server signing off

READ Apr 05 16:22:37.948 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x60000107ae40

235 2.7.0 Accepted

WROTE Apr 05 16:22:37.948 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.gmail.com -- port:587 -- socket:0x6080004d4c10 -- thread:0x60000107ae40

QUIT

READ Apr 05 16:22:37.979 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x600001065f80

* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE ENABLE MOVE CONDSTORE ESEARCH

3.127 OK richard.themortgagecentre@gmail.com Richard McKay authenticated (Success)

WROTE Apr 05 16:22:37.980 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x600001065f80

4.127 CAPABILITY

READ Apr 05 16:22:38.163 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608000468240

* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE ENABLE MOVE CONDSTORE ESEARCH

4.127 OK Success

WROTE Apr 05 16:22:38.164 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x60000107ae40

5.127 LIST "" ""

READ Apr 05 16:22:38.223 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x600001065f80

235 2.7.0 Authentication succeeded

WROTE Apr 05 16:22:38.223 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c8420 -- thread:0x600001065f80

QUIT

READ Apr 05 16:22:38.347 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x608001073680

* LIST (\Noselect) "/" "/"

5.127 OK Success

WROTE Apr 05 16:22:38.348 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:imap.gmail.com -- port:993 -- socket:0x6000004cab80 -- thread:0x600001065f80

6.127 LOGOUT

I asked you to post your settings here, I am not going to make guesses without seeing them.

Sorry Csound I posted a screenshot but it didn't pull through.

smtp.live.com

default ports

use ssl

authentication: password

You have entered this wrong (or it is corrupted)

The email address the SMTP server in the picture is incorrect, there should be an @ sign in it.

Look above the info panel to see the string in use (by the arrow)

You have not entered your email address correctly in your account settings.

You put "rmk1234hotmail.com" instead of "rmk1234@hotmail.com"

That's what you get the error

We can see that in your log :

WROTE Apr 05 16:21:47.337 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

MAIL FROM:<rmk1234hotmail.com>

READ Apr 05 16:21:47.442 [kCFStreamSocketSecurityLevelTLSv1_0] -- host:smtp.live.com -- port:587 -- socket:0x6000004c6d60 -- thread:0x608001061600

501 5.5.4 Invalid Email address

Thank you very much Vincent. the 1 year wait is finally over.

I had this problem yesterday, I could send on my phone and on my pc. I didn't feel up to the complicated instructions on this forum. Thought about it for a while, then popped down to my daughters house. As soon as my iPad picked up her wifi signal, off went my test email.

So I thought it was my virgin media broadband up the creek. Came home but before ringing virgin, I tried sending from home again and it worked! So whether simply getting out of wifi range then back in, did it I don't know.

My son in law said maybe it reset the STMP, what ever that is. If it happens again I will try turning off wifi and cellular network on iPad, then back on again, that may

save trotting off to my daughters house.

I am a practical, logical, non techy 67 year old.

Hi MacUsers

My problem has that I send many mails from my Hotmail on my MacBook to parents in school in BCC => Microsoft blocks me.

I work in different countries and some of these countries force me to use VPN so my location is constantly changing => Microsoft blocks my mail, hence I am used to the Hotmail/Outlook routine to get my account working again including changing passwords.

Last time it did not work.

I focused on sending all my mails from my iPhone and that worked almost OK while I tried the different tricks to get it back. Today I found the problem, the keychain had not been properly updated so the POP account had correct password but the SMTP server and the old much longer password, I updated the SMTP password and now mail is flowing out of my Macbook again ;-))

In Mail, choose Window > Connection Doctor.

Tip: If you see a spinning gear in Mail or the Mail Connection Doctor, choose Window > Activity to learn what Mail is doing.

This is where you check that SMTP and POP have the same password: good luck and Happy New Year.

I have also been nearly 12 months with the same problem. Had BT hub installed and lost the ability to send emails from hotmail account but I could still receive them. I had no problem with other devices just my apple mac - I have just tried out your advice and IT WORKS !!!!!! I am not technical in any way, in fact I'm useless when it comes to computers, I followed your advice step by step and it is simple. Thank you so much. YOU ARE A GENIUS XXX

Hey,

I found this worked for me, just check your hotmail settings are as follows

You change your POP to IMAP like this

Outlook.com does support IMAP and SMTP.

Incoming server:

IMAP: imap-mail.outlook.com

Port: 993

Encrypted Connection: SSL

Outgoing server:

SMTP: smtp-mail.outlook.com

Port: 25 or 587

Encrypted Connection: TLS

Username: Your Username

Password: Your Password

This won't work on mac os x mail unless you disable pop in your outlook.com account first. If you have mac os x mail, and you don't disable pop in your outlook.com account first, mail will automatically setup pop and smtp.

http://answers.microsoft.com/en-us/windowslive/forum/mail-email/how-to-set-up-ma c-mail-to-sync-your-outlookcom/afdfe981-20c7-4d4a-b6b1-9329b27f018a?tm=137900934 3708

http://answers.microsoft.com/en-us/outlook_com/forum/oemail-osend/how-to-set-up- mac-mail-to-sync-your-outlookcom/afdfe981-20c7-4d4a-b6b1-9329b27f018a