Very strange error on Outlook 2003

I have the weirdest situation here and I'm struggling to understand why:

1. My hotmail POP3 account works fine on my old Windows XP (32bit) machine, using Outlook 2003.

2. The exact same account, with identical credentials on my Windows 7 (64bit) machine, using Outlook 2003, fails to send emails (receiving is fine) with the following error message:

Task 'pop3.live.com - Sending' reported error (0x800CCC7D) : 'Your outgoing (SMTP) server does not support SSL-secured connections. If SSL-secured connections have worked in the past, contact your server administrator or Internet service provider (ISP).'

3. Disabling the firewall on the Windows 7 machine did not make a difference. I did not have to disable the firewall on the Windows XP machine. Both are running Zonealarm.

4. Both machines are physically in the same room, using the same ISP. The only difference is that the Windows XP is a (wireless) laptop but I don't think that makes any difference.

I'm really stuck, so any ideas welcome...

Thank you both for responding so quickly.

Apologies for omitting this from my earlier post. I already have other POP3 accounts which work fine with the "default" 110/25 settings. The problem is that Hotmail requires some specific settings as seen here:

Hotmail POP3 Configuration

So at the moment I am using:

• POP3 port 995, with encryption selected; and
• SMTP port 587 with encryption selected.

For the record SPA Authentication is not selected.

These are the settings that work fine on my XP machine but fail on my Windows 7 one.

The strangest past is this: when I click on "Test Account Settings", it completes with no errors on my W7 machine, but then... when I try to actually send an email then I get the 0x800CCC7D error.


So, this is the error message if I keep 587 but disable SSL:

Task 'pop3.live.com - Sending' reported error (0x800CCC78) : 'Unable to send the message. Please verify the e-mail address in your account properties. The server responded: 530 5.7.0 Must issue a STARTTLS command first'

Task 'pop3.live.com - Sending' reported error (0x800CCC7C) : 'Your outgoing (SMTP) server requires an SSL-secured connection. On the Tools menu, click E-mail Accounts, select View or change exisiting e-mail accounts, click Next, select the account, and then click Change. Click More Settings and then on the Advanced tab select This server requires an encrypted (SSL) connection. The server responded: 530 5.7.0 Must issue a STARTTLS command first'



and this is the error message when I try 25 again with no SSL:

Task 'pop3.live.com - Sending' reported error (0x80042109) : 'Outlook is unable to connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'

Task 'pop3.live.com - Sending' reported error (0x80042109) : 'Outlook is unable to connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).'


Appreciate your help.

Thanks

Hi there,

have you had time to look at this?

Thanks for your help.

Thanks for your reply Kari.

What I'm struggling to understand is why the same settings work on my Windows XP machine and not on Windows 7. So I don't think it has anything to do with Outlook itself, there must be some other issue that is related to the PC itself or to Windows 7?

Many thanks

Kari, no worries - not a stupid question. I can confirm that it is enabled and even more strangely the "Test Account Settings" process completes with no errors. I have no idea what's going on...

Hi Kari, any luck with this? Many thanks