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

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.

Comments

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

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

bojoda

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

Would prefer to continue using Outlook Express

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.

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.

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.

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