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Windows 7: Very strange error on Outlook 2003

02 Dec 2010   #1
No expert

Windows 7 Home Premium (64-bit)
 
 
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...


My System SpecsSystem Spec
.
02 Dec 2010   #2
Hopalong X

Windows7 Pro 64bit SP-1; Windows XP Pro 32bit
 
 

I had that happen to me.

Open Outlook. Click Tools> E-mail accounts.

Picture 1 top left
Check View or change existing email account> Next

Click Change in second picture. Top right.

Picture 3 Bottom left
Uncheck Log on using Secure password Authentication.
Click more settings.

Picture 4 Bottom right.
Advanced Tab Uncheck both SSL boxes. Empty boxes as in picture.
Click okay close any open windows.

Mike
My System SpecsSystem Spec
02 Dec 2010   #3
Kari

 

Open the account settings on both XP and Seven, compare that these settings are the same on both machines:

- Incomimg server port number
- Outgoing server port number

Very strange error on Outlook 2003-outlook_ports.png

Notice please: the port numbers 110 & 25 in my screenshot are from an account of mine. Yours can be something different. Important is that you put those working port numbers from your XP mail settings to Seven.

Selection This server requires an encrypted connection should be disabled, not checked on both machines.

Kari


My System SpecsSystem Spec
.

02 Dec 2010   #4
No expert

Windows 7 Home Premium (64-bit)
 
 

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
My System SpecsSystem Spec
04 Dec 2010   #5
No expert

Windows 7 Home Premium (64-bit)
 
 

Hi there,

have you had time to look at this?

Thanks for your help.
My System SpecsSystem Spec
04 Dec 2010   #6
Kari

 

I tested this, changing three different Hotmail accounts from IMAP to POP3. I used three accounts to test because I wanted to see if there's a difference when using a @live.com, @msn.com or @hotmail.com account.

No difference, all accounts sending and receiving well from XP / Outlook 2003, Vista / Outlook 2007 and Seven / Outlook 2010, using these settings:

Very strange error on Outlook 2003-hotmail_pop_settings_1.png Very strange error on Outlook 2003-hotmail_pop_settings_2.png

Notice that using SSL encryption gave always a sending error, on all platforms. Using TLS, no problems whatsoever.

Kari


My System SpecsSystem Spec
05 Dec 2010   #7
No expert

Windows 7 Home Premium (64-bit)
 
 

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
My System SpecsSystem Spec
05 Dec 2010   #8
Kari

 

Sorry if you feel this is a stupid question, but did you check that Outgoing Server tab (first image in my previous post)? The option My outgoing server requires authentication must be enabled. Setting the ports and encryption alone is not enough.
My System SpecsSystem Spec
05 Dec 2010   #9
No expert

Windows 7 Home Premium (64-bit)
 
 

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...
My System SpecsSystem Spec
09 Dec 2010   #10
No expert

Windows 7 Home Premium (64-bit)
 
 

Hi Kari, any luck with this? Many thanks
My System SpecsSystem Spec
Reply

 Very strange error on Outlook 2003




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