Cannot send email via Hotmail through port 587 with Secure Connection (SSL) set

[elecman]

Something is blocking my attempts to send email (with Outlook Express) via my hotmail.com account. The error I receive is as follows:

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Your server has unexpectedly terminated the connection. Possible causes for this include server problems, network problems, or a long period of inactivity. Account: 'Hotmail', Server: 'smtp.live.com', Protocol: SMTP, Port: 587, Secure(SSL): Yes, Error Number: 0x800CCC0F

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When Hotmail.com first changed over to a POP3 server (Sept 2009), I could send emails through them using port 587, which they require. But then something happened, with no changes on my part, to disable my ability to send.

I have checked and rechecked my Outlook Express account settings. I can send email through another third-party mail account (at 1&1 Internet.com) using port 587, which does not require setting SSL to yes. I can also ping the Hotmail SMTP server via port 587 and receive a response from it.

I connect to Verizon DSL via a Westell 327W modem/router. Clearly it is not blocking port 587 without SSL. Does it have the capability to block SSL traffic? Or is the Verizon server the culprit, not allowing emails to be sent via Hotmail.com?

Two different computers on my LAN have the same problem sending emails via Hotmail.com. I have tried everything the Hotmail people have suggested; at this point they think it is an ISP problem, hence this post. This problem doesn't make sense to me and is driving me crazy. Can anyone help me with this?

Thanks.

[bojoda]

Error started 10/27/09

A secure connection to the server could not be established. Account: 'bojoda HMLive', Server: 'smtp.live.com', Protocol: SMTP, Port: 587, Secure(SSL): Yes, Error Number: 0x800CCC1A

Using Outlook Express

[bojoda]

Using Outlook 2003 + Outlook Connector, smtp.live.com port 587 SSL  sends mail without error

Would prefer to continue using Outlook Express

[susanchao]

We use Outlook Express and expericed the exact the same problem, which can not send any email. We got the same error message. I re-set the account info from Outlook Express. But we can receive the emails. Any idea? Looks like something or port block the sending out email?

Any Verizon problem?

Susan

[Bonnie_G]

I'm not sure if my problem was the same as the problems described in this thread so far, but my story may help you all.

I have a small business but cannot afford a website with Verizon. Before getting DSL, I used a dialup service at an ISP that hosted my website. Because my domain is what I prefer to use for e-mail, I continued to use my old ISP just for e-mail and use my Verizon account as a secondary e-mail account.

When that letter arrived in September, I tried to determine what I needed to do. I was told not to do anything until after September 22. On that date, when I sought assistance and got instructions from Verizon and my other ISP, nothing worked. Nobody knew what was wrong. The other ISP tried different ports and still nothing worked.

Finally, I said to myself, "See what happens when you use "outgoing.verizon.net" as the outgoing mail server (SMTP) instead of my other ISP." The techs at my old ISP and at Verizon were stumped, but I had the right answer.

So try that, guys, and see if it works. When I found my solution, I thought about posting it somewhere but didn't try to find a forum for it. Today I have another need and saw this thread, and I decided to pass this along.

I hope it's the right solution for you, too. In other words, you can send messages to any server as long as they go first through Verizon from your computer.

[elecman]

Bonnie_G,

I don't think I understand what you're suggesting. How is this any different from just using my Verizon account to start with?

If Verizon is going to be the outgoing server, why do I need my other, third-party, provider's server? And how would Verizon's server know the name of the third-party outgoing server?

Or is this using one provider (Verizon) to send with, and the other (Microsoft Live - Hotmail in my case) to receive with?

Lot's of questions, I know, but it's because I'm confused.

[Bonnie_G]

Yes, send mail via Verizon's outgoing mail server, but receive mail through the third-party's incoming mail server. The address is that of the third-party e-mail.

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elecman wrote:

Bonnie_G,

I don't think I understand what you're suggesting. How is this any different from just using my Verizon account to start with?

If Verizon is going to be the outgoing server, why do I need my other, third-party, provider's server? And how would Verizon's server know the name of the third-party outgoing server?

Or is this using one provider (Verizon) to send with, and the other (Microsoft Live - Hotmail in my case) to receive with?

Lot's of questions, I know, but it's because I'm confused.

---

[elecman]

Thanks for the idea; it was entertaining to think about. However...

I think this approach just side-steps the original problem without fixing anything. And it introduces a confusion factor. I have to remember to transmit on my Verizon account when I reply to a message, and my correspondent sees my reply come from an address different from the one that he used to send his message to me. If he in turn simply clicks the Reply button, his next message will come back to me via my Verizon account.

Therefore, if my third party mail provider is where I employ my unique domain name (which I pay for), then any advantage gained from using that domain to identify me disappears after the first message. Or, if I want to have some control over the mail I receive, I may not want to reveal two of my email addresses to every correspondent, which is what this technique would do.

I still want to know why Verizon, as my DSL provider, won't let me send secure SSL email via my third party provider. It worked fine for a while and then, without any changes on my part, it ceased to work. Very suspicious, and irritating.

[somegirl]

You can still have your reply address set to your hotmail address. And you don't have to really remember to do anything. Configure your client for the HOTMAIL account with Verizon's outgoing server. It will automatically send via Verizon. You don't reveal your verizon.net address, you are just using their server to transmit.

[elecman]

somegirl,

　

You are correct. I now understand what you're saying. I've tried it and it works. Thank you for your patience.

　

Now I'd like to document the account settings in more detail, addressing this to any other Verizon subscribers who may be interested. (I hope the formatting of this message survives the posting process.)

　

The purpose here is to alter your Outlook Express 6 settings for the account you use to access your third-party POP3 mailbox provider, where attempting to send an e-mail results in an error message like this:

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Your server has unexpectedly terminated the connection. Possible causes for this include server problems, network problems, or a long period of inactivity. Account: 'Hotmail', Server: 'smtp.live.com', Protocol: SMTP, Port: 587, Secure(SSL): Yes, Error Number: 0x800CCC0F

---

The third-party account defined in Outlook Express is modified to use the Verizon outgoing server. This technique is a work-around, not a cure. The drawback is that it requires two mail providers where only one should be needed (that one would be Hotmail in my case). But because you specify a Reply address for the account, the receiver of your e-mail does not see that it was sent via a different server.

　

For clarity, I will assume that Microsoft Live (Hotmail) is the third-party provider, using the following servers: "pop3.live.com" (incoming mail), and "smtp.live.com" (outgoing mail). I will use the following example e-mail addresses: "name1@hotmail.com" and "name2@verizon.net".

　

1. Start Outlook Express, click Tools, click Accounts...

2. Click the account name for the third-party provider, click Properties

     (or, if desired, create a new account and modify it as shown here)

3. Click General tab (if not already there):

     a. Mail Account: modify name if desired (this name appears in the account list).

     b. User Information:

          1. Name: type name you want to appear in e-mail receiver's From field

          2. E-mail address: "name1@hotmail.com"

          3. Reply address: type "name1@hotmail.com"

              (This is key, so that replies come back via Hotmail, not Verizon)

     c. Click Apply

4. Click Servers tab:

     a. Server Information:

          1. My incoming mail server is a POP3 server

          2. Incoming mail (POP3): "pop3.live.com"

          3. Outgoing mail (SMTP): replace "smtp.live.com" with "outgoing.verizon.net"

     b. Incoming Mail Server:

          1. Account name: "name1@hotmail.com"

          2. Password: if not there already, type the password for "name1@hotmail.com"

          3. Check: Remember password

          4. Do not check: Log on using Secure Password Authentication

     c. Outgoing Mail Server:

          1. Check: My server requires authentication

          2. Click Settings...

                   Select: Log on using

                   Account name: "name2@verizon.net"

                   Password: type the password for "name2@verizon.net"

                   Check: Remember password

                   Do not check: Log on using Secure Password Authentication

                   Click OK

     d. Click Apply

5. Click Advanced tab

     a. Server Port Numbers

          1. Outgoing mail (SMTP): type 587 (or 25 if Verizon accepts that)

          2. Do not check: This server requires a secure connection (SSL)

                    (SSL is not used by Verizon)

          3. Incoming mail (POP3): type 995

                   (995 required by Hotmail, others might use 110)

          4. Check: This server requires a secure connection (SSL)

                   (SSL is required by Hotmail)

     b. Click Apply

6. Click OK

7. Click Close

　

I chose to create a new "cross-server" account so that I could maintain my original Hotmail account for possible future use. Both were set (using Delivery option on Advanced tab) to leave a copy of a retrieved message on the server for 5 days. When I tried my new account. I noticed a curious result. After sending a message to the Hotmail server, I was able to retrieve that message twice, once with the new ("cross-server") Hotmail account and once with the original Hotmail account. However, neither account by itself could retrieve the message twice. If the first account to retrieve the message was not set leave a copy on the server then the other account could not retrieve the message. Apparently, messages are read and "saved" on a per-account basis, but deleted globally (removed from the server). I conclude, therefore, that it is Outlook Express, not the mail server, that maintains the read and save status of the messages. I hadn't realized this before now.

[Hubrisnxs]

I don't think VZ uses SSL with their connection set ups, so maybe that is the problem.   ??

EDIT*  I just googled hotmail pop settings, it appears they use ssl, so yes you probably need it.   sorry about that.

[jeffsupersaiyan]

try port 119 or 443

[elecman]

Same negative result, same error message, with ports 119 and 443. Still cannot send a message via Hotmail.

Thanks anyway.