Windows Live Hotmail POP3/SMTP broken

[N. Miller]

I tested the POP3/SMTP settings first in MS Outlook Express 6. POP3 worked:

Incoming email: 'pop3.live.com:995', SSL enabled. Used full email address as
the user name, and the account password. Email downloaded properly.

However, try another POP3 client, and I have trouble. I configured the
Mercury/32 Distributing POP3 Client to access 'pop3.live.com:995'. I
selected, "Via direct SSL". The connection failed, as shown by the session
log:

| 15:47:42.359: --- Fri Feb 13 15:47:42 2009 ---
| 15:47:42.375: Connect to 'pop3.live.com', timeout 30.
| 15:47:44.562: 22: Error -32 activating SSL session (locus 6014, type 4, code 0, 'Server provided a broken/invalid certifi')
| 15:47:44.562: --- Connection closed normally at Fri Feb 13 15:47:44 2009. ---
| 15:47:44.562:

I also tested SMTP in MS Outlook Express 6:

Outgoing email: 'smtp.live.com:25', SSL enabled. Used full email address as
the user name, and the account password. Email was properly sent.

Outgoing email: 'smtp.live.com:587', SSL enabled. Used full email address as
the user name, and the account password. Email was properly sent.

At this point, I'd like to interject that using SSL on port 587 is not
supported by RFC 4409. SSL is not even mentioned in RFC 4409, but STARTTLS
is. Just another case of Microsoft doing things the Microsoft way, instead
of the standard way, I guess.

Now to the problem. I configured Pegasus Mail to use 'smtp.live.com:587'.
Initially selecting, "Via direct SSL", then, when that failed, by selecting,
"Via STARTTLS". Keep this in mind: Pegasus Mail works properly on servers
implementing SSL on port 465, and it also works properly on servers using
port 587, with, or without STARTTLS. But not with 'smtp.live.com'.

| Via direct SSL connect:
| -----------------------
|
| << No trace information available >>
|
| Pegasus Mail session log:
| -------------------------
|
| --- Wed, 18 Feb 2009 16:41:02 ---
| Connect to 'smtp.live.com' port 587, timeout 30.
| 16:41:02.546 [*] Connection established to 65.55.172.254
| 16:41:02.640 22: Error -32 activating SSL session (locus 6014, type 4, code 0, 'Unexpected packet type 50, expected 22')
| 16:41:02.640 --- Connection closed normally at Wed, 18 Feb 2009 16:41:02. ---\0A\0A

On the off chance that, maybe, Microsoft did this by the Internet standard
(but when have they *EVER* done anything by somebody else's standard), I
then tried TLS:

| Via STARTTLS:
| -------------
|
| [*] Connection established to 65.55.172.254
| >> 0130 220 BLU0-SMTP14.blu0.hotmail.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.2668 ready at Wed, 18 Feb 2009 16:37:17 -0800
| << 0023 EHLO [192.168.102.34]
| >> 0056 250-BLU0-SMTP14.blu0.hotmail.com Hello [68.127.105.99]
| >> 0010 250-TURN
| >> 0019 250-SIZE 35840000
| >> 0010 250-ETRN
| >> 0016 250-PIPELINING
| >> 0009 250-DSN
| >> 0025 250-ENHANCEDSTATUSCODES
| >> 0014 250-8bitmime
| >> 0016 250-BINARYMIME
| >> 0014 250-CHUNKING
| >> 0010 250-VRFY
| >> 0009 250-TLS
| >> 0014 250-STARTTLS
| >> 0008 250 OK
| << 0010 STARTTLS
| >> 0029 220 2.0.0 SMTP server ready
| 22: Error -32 activating SSL session (locus 6014, type 4, code 0, 'Server provided a broken/invalid certificate, try again with a reduced level of certificate complian')

So much for Windows Live Hotmail not being "proprietary"!

--
Norman
~Oh Lord, why have you come
~To Konnyu, with the Lion and the Drum

[...winston]

I can't provide any guidance..but I can state that..
I've tested 12 different Live ID accounts(hotmail, live, msn.com) with the Pop3/Smtp settings and they all work in OE, WM, Outlook
2003, Outlook 2007, and WLM.
- the only variation in settings occurs in OL2007 which only works when TLS is enabled(not SSL).

--
...winston
ms-mvp mail

"N. Miller" <anon...@msnews.aosake.net> wrote in message news:6f88z190kfeg$.dlg@msnews.aosake.net...

[N. Miller]

On Wed, 18 Feb 2009 20:19:05 -0500, ...winston wrote:

> I can't provide any guidance..but I can state that..
> I've tested 12 different Live ID accounts(hotmail, live, msn.com) with the Pop3/Smtp settings and they all work in OE, WM, Outlook
> 2003, Outlook 2007, and WLM.
> - the only variation in settings occurs in OL2007 which only works when TLS is enabled(not SSL).

I won't try Windows Live Mail. It works with DeltaSync. My intent was to try
and get it to work with my main squeeze. I use Mercury/32, the Distributing
POP3 Client, to fetch all POP3 email. The email is downloaded onto my mail
server, in the store on that networked computer. The client I use, Pegasus
Mail, works with Mercury/32 similar to the way MS Outlook works with MS
Exchange. All email on the networked email store can be read from any other
networked computer using Pegasus Mail.

Anyway, I just tried Mozilla Thunderbird 2.0.0.19. Like MS Outlook, it
requires STARTTLS. And it does work that way. Just need to find out why
Pegasus Mail throws the SMTP error when configured for port 587 with
STARTTLS. And why Mercury/32 is also throwing its error on access via SSL
for port 995.

[...winston]

WLM supports Pop3, Imap, and DeltaSync. DeltaSync is only applicable to Hotmail type accounts(hotmail.com, live.com,
msn.com)accounts and is the default http server when automatically setting up all Hotmail accounts. Hotmail
accounts(country/region permitting) in WLM can be configured for pop3 and also where applicable(grand-fathered, premium primary
account and/or subaccount) for the WebDAV server(which has yet to be deprecated).

If you figure it out, I'd be interested to hear more.

Thanks again.

--
...winston
ms-mvp mail

"N. Miller" <anon...@msnews.aosake.net> wrote in message news:1rr6hb0yqnml6$.dlg@msnews.aosake.net...

[N. Miller]

On Thu, 19 Feb 2009 01:15:40 -0500, ...winston wrote:

> WLM supports Pop3, Imap, and DeltaSync. DeltaSync is only applicable to Hotmail type accounts(hotmail.com, live.com,
> msn.com)accounts and is the default http server when automatically setting up all Hotmail accounts. Hotmail
> accounts(country/region permitting) in WLM can be configured for pop3 and also where applicable(grand-fathered, premium primary
> account and/or subaccount) for the WebDAV server(which has yet to be deprecated).
>
> If you figure it out, I'd be interested to hear more.

I have free Hotmail accounts. If I could get Mercury/32 to work with them, I
would not need a DeltaSync, or WebDAV client (two of the accounts are too
new for WebDAV to work).

I have posts in the Mercury/32, and the Pegasus Mail news groups. Will see
if they have any ideas.

[PA Bear [MS MVP]]

FYI, Norman:

Hotmail Online Solutions Center (new & replaces all newsgroup & email format
support)
http://windowslivehelp.com/Default.aspx

Solutions for Common Problems
http://windowslivehelp.com/solutions/

Hotmail Community Forums <=post your comments here instead!
http://windowslivehelp.com/community/Default.aspx
--
~PA Bear