Tools > Account Settings > Outgoing Server(SMTP)

Have you configured your Outgoing server to use port 25 ? some servers block port 25. Suggest you try port 587

Check 'Authentication Method' = Normal password If this is not selected it can cause a rejection.

Do you use Spamassassin? I have heard that any emails forwarded with spamassassin headers can apparently get rejected/cause issues.

Outgoing port is 995 tried 587 but that didn't work either 'Authentication Method' = Normal password" is checked No, not using Spamassassin

It's not uncommon for entire IP ranges used by popular webmail services to be banned from other commercial / company / enterprise providers.

Embarqmail may be blocking all of Hotmail, normally the bounce message shows detailed information on why this is and how to address the issue. Can you share the bounce message (while removing your personal / the recipient's information)?

How did you configure Thunderbird for your Hotmail account?

I think the problem is definitely with Thunderbird. If I send thru the Hotmail web browser, it goes thru fine. Same if i send thru Windows Live Mail. Only gets bounced when I send thru Thunderbird. Here is the bounced info:

--9B095B5ADSN=_01CFBD46F5877B500001CB81BLU004?OMC3S11.h Content-Type: message/delivery-status

Reporting-MTA: dns;BLU004-OMC3S11.hotmail.com Received-From-MTA: dns;BLU437-SMTP54 Arrival-Date: Sat, 23 Aug 2014 10:01:05 -0700

Final-Recipient: rfc822; xxxxxxx@embarqmail.com Action: failed Status: 5.7.1 Diagnostic-Code: smtp;554 5.7.1 [P4] Message blocked due to spam content in the message.

--9B095B5ADSN=_01CFBD46F5877B500001CB81BLU004?OMC3S11.h Content-Type: message/rfc822

Received: from BLU437-SMTP54 ([65.55.116.74]) by BLU004-OMC3S11.hotmail.com over TLS secured channel with Microsoft SMTPSVC(7.5.7601.22712); Sat, 23 Aug 2014 10:01:05 -0700 X-TMN: [ZLk5pVrhU9BEnJRV02lodDZF3xrw0VgY] X-Originating-Email: [xxxxxxx@hotmail.com] Message-ID: <BLU437-SMTP5445ABFCE4AA8EC82F34DFC7D10@phx.gbl> Return-Path: xxxxxxx@hotmail.com Received: from [192.168.1.104] ([71.55.251.152]) by BLU437-SMTP54.smtp.hotmail.com over TLS secured channel with Microsoft SMTPSVC(8.0.9200.16384); Sat, 23 Aug 2014 10:01:04 -0700 Date: Sat, 23 Aug 2014 13:00:57 -0400 From: Lee D <xxxxxxx@hotmail.com> User-Agent: Mozilla/5.0 (Windows NT 6.1; WOW64; rv:31.0) Gecko/20100101 Thunderbird/31.0 MIME-Version: 1.0 To: Lee Embarq <xxxxxxx@embarqmail.com> Subject: testing Content-Type: multipart/alternative; boundary="------------060407040006010402040705" X-OriginalArrivalTime: 23 Aug 2014 17:01:04.0719 (UTC) FILETIME=[D33A7DF0:01CFBEF3]

Content-Type: text/plain; charset="utf-8"; format=flowed Content-Transfer-Encoding: 7bit

testing

Content-Type: text/html; charset="utf-8" Content-Transfer-Encoding: 7bit

<meta http-equiv="content-type" content="text/html; charset=utf-8"> <font face="Arial">testing</font>

--9B095B5ADSN=_01CFBD46F5877B500001CB81BLU004?OMC3S11.h--

Diagnostic-Code: smtp;554 5.7.1 [P4] Message blocked due to spam content in the message.

We've seen stuff like this before, usually with yahoo. Thunderbird is working to the standards, and some idiot at yahoo tries to "improve" the service or the anti-spam performance, and suddenly all Thunderbird mail is rejected because it's using uppercase rather than lowercase, or some other equally trivial but perfectly legal variation.

Something in the Thunderbird-formatted message is now triggering a spam warning. Now if you're not actually sending spam, it HAS to be a problem at the other end, yes? Are you using a signature with links to other sites? Are you referencing other sites or URLs in your messages?

Actually, since the "reporting mta" is hotmail:

Reporting-MTA: dns;BLU004-OMC3S11.hotmail.com

it appears to be hotmail, not embarqmail that is raising the rejection. That makes sense; hotmail would be less likely to reject material sourced by their own email client, which is almost certainly a proxy for the hotmail webmail service.

It's also possible that since Thunderbird uses the regular POP, IMAP and SMTP protocols, your message sent with Thunderbird arrives at hotmail via a different route that is subject to some filtering that doesn't take place if you use hotmail's webmail portal or its proprietary live mail client, which itself probably uses a proprietary MS protocol.

Zenos got that right, email sent through SMTP goes through a different route.

I iuse MXTools to analyze the headers, it doesn't seem Hotmail is blacklisted here. It's not a quick thing to troubleshoot.

My advice in this specific case, if this is important email that you want to talk someone about troubleshooting when it doesn't work, use a commercial email/hosting provider, don't use Hotmail.

There is NOTHING in the email I send, just the word "test". No signature, no URL. Did I mention that I am sending from Thunderbird (via Hotmail) to my own embarq email account and it gets bounced.

1. Test all alone may be considered SPAM by Hotmail. Try putting in a whole sentence.
2. If you have no subject. Insert one.
3. If you have Reply-to set in your account settings remove it. If it is not set insert it. (both states have been reasons for spam detection in the past.)
4. Ensure if you have reply-to that is is the same hotmail address your sending from.
5. If it is a hotmail alias it may well be a hotmail bug
6. Ensure the from email address is using an outgoing SMTP server that uses the correct email address credentials. That is the user name in the SMTP server matches the email address.