Outgoing mail server issues

Question

Hello.

I use Windows Live Mail to receive, send, and file my business email. I have four email accounts through my business's web site. As such the address for all four email accounts uses the format (email)@(mybusinessdomain).com. When I am in the home office, where I use Optimum for my internet connection, my outgoing server name is mail.optonline.net. My incoming server is pop.hosting.earthlink.net.

I have been on the road visiting family, and so far I have been able to modify the outgoing mail server name to those specified by each cable internet provider used by the family/friend with whom I've been staying, and I have been largely successful in sending, as well as receiving my business emails. Because my web host, Earthlink downloads to my PC my emails upon request, I have not had to change that in order to successfully receive emails. Changing the outgoing server has, so far, enabled me to send emails as well.

The family with whom I am currently visiting uses Comcast, and I changed the outgoing mail server to that which I discovered on the web--smtp.comcast.net. As recommended, I set up the outgoing server port to either 587 or 465+SSL=yes. With both settings I received an immediate error message. That message was...

The message could not be sent because the server rejected the sender's email address. The sender's email address was '******@co-optoolkit.com'.

Subject 'test'

Server Error: 550

Server Response: 550 5.1.0 Authentication required

Server: 'smtp.comcast.net'

Windows Live Mail Error ID: 0x800CCC78

Protocol: SMTP

Port: 587

Secure(SSL): No

I then tried changing the server name to  mail.comcast.net (trying it first with the port 587, then 465+SSL=yes). Each time this caused a long delay in sending an email, with an eventual error message. That message was...

The connection to the server has failed.

Subject 'test'

Server: 'mail.comcast.net'

Windows Live Mail Error ID: 0x800CCC0E

Protocol: SMTP

Port: 587

Secure(SSL): No

Socket Error: 10060

My web hosting company, Earthlink, may be able to shed some light on this, and I have called them, but they are closed today, as it is Sunday.

I need to be able to communicate with my clients while I am away.

Is there something I have overlooked in setting this up?

Thank you,

Barbara

Answer 1

You are experiencing this fault only with some Email Service Providers, not all of them, most likely because some of them are using a different system for handling e-mail.

Log-in to your e-mail account on the Email Service Provider's website, with CenturyLink, Comcast, or AT&T (the ones currently not working).

Once logged-in, deal with any alert, and then go to the account's security settings and check whether you've enabled two-factor authentication. If you haven't done that, try enabling it. Save the changes.

But also read-up on their FAQ page about how to use two factor authentication with their service.

Usually, you have to follow a carefully designed process to generate a special password, and then must use that password in Windows Live Mail (it's a 2nd password, it's not a replacement for your Account password). The process might be different for each service provider.

Do that: generate the 2nd password, then use it in Windows Live Mail.

It should then be possible to send from and receive to your account, in Windows Live Mail, but only whilst Windows Live Mail is configured to use that particular Email Service Provider. In practice, you will presumably need to create and use a second password for all the affected sites.

If possible, make life easier for yourself by using the same 2nd password with each of the affected sites.

Answer 2

A few comments:

It's not normally necessary nowadays to use SMTP server belonging to the ISP you happen to be using. The usual reason why people have difficulty sending mail when away from home is that the account is set up to use unauthenticated SMTP, often over port 25. Many Email Service Providers now won't allow this, because these settings make it easy for spammers. You should find that your Optimum account will work anywhere if you set it up as follows:

  

Right-click on the account name in the folder pane and select Properties. 

• On the Servers tab   

   

- Ensure that the *Email username*is your full email address
- Select *Log on using clear text authentication*
- Select *My server requires authentication*

• On the Advanced tab   

   

- Ensure that *This server requires a secure connection (SSL)* is selected for outgoing mail.
- Ensure that the server port for outgoing mail is **465**

• Click Apply and OK

Remove any unsent messages from the outbox (below the account folders in the folder pane), then compose a new test message with a unique subject and send it to yourself. Post any new error message in your reply.

As regards the Comcast settings, you should be using SSL (most major ESPs now require it). As regards the lack of authentication, this is turned on by the setting on the Servers tab: My server requires authentication. In this case, you would also need to enter a username (usually an email address) and password that the server will recognize, i.e. belonging to a Comcast account holder.

You're seeing an error when trying to connect to mail.comcast.net by SMTP, because this is an alias for the Comcast IMAP servers. The SMTP servers are called smtp.comcast.net. You'll often find useful information on the ESP website; for Comcast, that would be https://www.xfinity.com/support/articles/email-client-programs-with-xfinity-email 

I did what you recommended. It appeared it was going to work, as I saw...

Connecting

Sending

Then I saw Error !

But when I clicked on Error ! to copy the error message for you, it was blank.

Thank you for your help.

Barbara

Answer 3

A few comments:

It's not normally necessary nowadays to use SMTP server belonging to the ISP you happen to be using. The usual reason why people have difficulty sending mail when away from home is that the account is set up to use unauthenticated SMTP, often over port 25. Many Email Service Providers now won't allow this, because these settings make it easy for spammers. You should find that your Optimum account will work anywhere if you set it up as follows:

Right-click on the account name in the folder pane and select Properties. 

• On the Servers tab   
  • Ensure that the Email usernameis your full email address
  • Select Log on using clear text authentication
  • Select My server requires authentication
• On the Advanced tab   
  • Ensure that This server requires a secure connection (SSL) is selected for outgoing mail.
  • Ensure that the server port for outgoing mail is 465
• Click Apply and OK

Remove any unsent messages from the outbox (below the account folders in the folder pane), then compose a new test message with a unique subject and send it to yourself. Post any new error message in your reply.

As regards the Comcast settings, you should be using SSL (most major ESPs now require it). As regards the lack of authentication, this is turned on by the setting on the Servers tab: My server requires authentication. In this case, you would also need to enter a username (usually an email address) and password that the server will recognize, i.e. belonging to a Comcast account holder.

You're seeing an error when trying to connect to mail.comcast.net by SMTP, because this is an alias for the Comcast IMAP servers. The SMTP servers are called smtp.comcast.net. You'll often find useful information on the ESP website; for Comcast, that would be https://www.xfinity.com/support/articles/email-client-programs-with-xfinity-email

Answer 4

I've never before encountered anyone, except the moderators here, who could understand - let alone operate - such a complicated e-mail setup. Congratulations.

However, it's a bit of a double-edged sword, because there are so many things which might go wrong.

My initial suspicion is that you are trying to use an e-mail service, i.e. Comcast, which requires two-factor authentication, but you are not operating that form of authentication, so your e-mails can't be processed by the Comcast email service.

Some companies require two-factor, some don't. You've maybe been lucky up to now, and only used those which don't.

The following might help, you can only try.  :-)

Log-in to your e-mail account on the website: so, log-in to your account on Earthlink's website.

Once logged-in, deal with any alert there, and then go to the account's security settings and check whether you've enabled two-factor authentication. If you haven't, try enabling it. Save the changes.

Then read-up on their FAQ page about how to use two factor authentication with their service. Usually, you have to follow a carefully designed process to generate a special password and then must use that password in Windows Live Mail (it's a 2nd password, it's not a replacement for your Account password).

Do that: generate the 2nd password, then use it in Windows Live Mail.

It should then be possible to send from and receive to your account, in Windows Live Mail, but only whilst Windows Live Mail is configured to use Comcast.

Thank you. I will certainly look into that. On the chance there is nothing easier, such as some setting in Live Mail that I have overlooked...

Since I have a few more stops on my trip that may require this (or other modifications) for other ISPs, I may continue to do what I am doing until I return to my home office. Right now, my business email is forwarding to an old AOL address of mine. I set that up so that when I am away from my PC, I can still know from a notification on my phone that I have client email waiting for me. I then reply from my AOL address, including my business address in the CC so that I still have a record of the conversation. I've been asking my clients to use Reply All so that I get the reply both in my business email and my AOL email.

Answer 5

I've never before encountered anyone, except the moderators here, who could understand - let alone operate - such a complicated e-mail setup. Congratulations.

However, it's a bit of a double-edged sword, because there are so many things which might go wrong.

My initial suspicion is that you are trying to use an e-mail service, i.e. Comcast, which requires two-factor authentication, but you are not operating that form of authentication, so your e-mails can't be processed by the Comcast email service.

Some companies require two-factor, some don't. You've maybe been lucky up to now, and only used those which don't.

The following might help, you can only try.  :-)

Log-in to your e-mail account on the website: so, log-in to your account on Earthlink's website.

Once logged-in, deal with any alert there, and then go to the account's security settings and check whether you've enabled two-factor authentication. If you haven't, try enabling it. Save the changes.

Then read-up on their FAQ page about how to use two factor authentication with their service. Usually, you have to follow a carefully designed process to generate a special password and then must use that password in Windows Live Mail (it's a 2nd password, it's not a replacement for your Account password).

Do that: generate the 2nd password, then use it in Windows Live Mail.

It should then be possible to send from and receive to your account, in Windows Live Mail, but only whilst Windows Live Mail is configured to use Comcast.