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General discussion

Outlook Send Mail Fails

Apr 29, 2018 2:01PM PDT

I've used Outlook mail client on Windows XP (Outlook 97) through Windows 10 (Outlook 2016) - POP3 protocol. About 2 weeks ago, send mail began to fail - messages stuck in Outbox. The failure is independent of version: (2010 on Intel based laptop; 2016 on my Intel based desktop). Both systems are running Windows 10 Pro 64-bit. I've read several articles on the Net but none provided success. I've also contacted my ISP, COX, who blames Microsoft. Of course, Microsoft blames my ISP. Assuming that the copy of Outlook as well as my Profile were corrupted, respectively, I re-installed Office 2016 on my desktop, tested sending mail which failed. Then I changed my Outlook profile, tested sending mail which also failed. I'm out of options to try. Have others who experienced this anomaly solved it? If yes, please share you solution. Thanks for your support

Discussion is locked

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Too many times.
Apr 29, 2018 2:44PM PDT

It's rarely the same thing but firewalls or AV suites are ditched then we go over the settings. Then we have to try POP3 or IMAP settings. The too often recurring issue that you just bite your tongue since you don't want to upset the client is when the web mail doesn't work either. So they have to get that working.

FINALLY we have the issue you can't send email if you are not on COX's network. Some folk didn't know that.

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Re; Too many times
Apr 29, 2018 3:36PM PDT

Robert,

So. true. Ironically, COX mail works if the access is via my iPhone, iPad and their "native" webmail. The issue with their webmail is that it is more primitive than some 1990s clients. Worse, their current webmail has significantly fewer clients than their previous versions. There are alternate mail solutions, but Outlook has the features on which I depend, e.g., .pst data files for mail archiving.

Until either COX or Microsoft blinks - I doubt the issue is the cause of the Big M - I'm stuck with using multiple devices for mail. What an interesting problem to be having in 2018, as we explore the frontiers of artificial intelligence and machine learning. Sigh!!

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So at this point ONLY web mail works.
Apr 29, 2018 3:55PM PDT

Web mail doesn't care where you are on the internet (for the most part,.)

I think we have to go over this area again. COX email won't send unless you are on your COX home/internet. They used to have a setup to allow sending out in the wild but I continue to read it's broken. So I never count on sending unless it's on the home internet.

https://www.cox.com/residential/support/pop-or-pop3-server-settings.html shows there are two ports for outgoing. You have to try both.

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Re: So at this point ONLY web mail works
Apr 29, 2018 5:47PM PDT

In late 2017, COX sent a message to users mandating upgrades to Port settings for both IMAP and POP3. I've always used POP3, and the required settings are: Incoming Port: 995; Outgoing Port: 465, i.e. SSL encryption. I'll try 587 (TLS) for Outgoing Port and report findings. Thanks for suggestion.

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Tried Outgoing Port 587 (TLS)
Apr 29, 2018 6:01PM PDT

I tried Outgoing Port 587 (TLS), and here's the response from the server:

"Send test email message: Your server does not support the connection encryption type you have specified. Try changing the encryption method. Contact your mail server administrator or Internet service provider (ISP) for additional assistance."

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There's also a checkbox.
Apr 29, 2018 6:18PM PDT

"place a check in the box next to My outgoing server (SMTP) requires authentication."

Also, you can try Thunderbird to get away from the Microsoft finger pointing.

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Re: There's also a checkbox.
Apr 29, 2018 8:27PM PDT

All test were with that box checked, and each option failed. It may be time for a different mail client and ISP.

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Outlook is an email client.
Apr 30, 2018 5:44AM PDT

Meaning all it does is receive and send email to your Email server at Cox. In the client you set up a in coming server and and out going SMTP server. These settings are the same for all email clients. The port information is supplied by the ISP or email host may be required for their specific setup. What do you mean native email? Do you mean using a browser? Using a browser is basically the same IMAP. POP3 emails account allow the client to go to the in message server and will download the emails to your PC. IMAP the emails stay on the server and aren't downloaded to your machine. You may be having an issue with Cox's POP3. Try seeing if setting up IMAP works.

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Re: Outlook is an email client
Apr 30, 2018 8:45PM PDT

Yes, Outlook is an email client which I've used on Windows and COX ISP successfully until recently. Being an engineer, I'm most frustrated when only one side of an interface fails which in this case is send mail. Despite COX's claim, I'm convinced that the issue is with their mail server (POP3 protocol). And, yes, I mean webmail when I refer to "native." The send mail issue has not occurred using web clients (Gmail, COX, Apple). I haven't tried IMAP and may over the coming weekend. Frankly, I'm fed up with COX overall as an ISP and the send mail issue pushes me close to the decision to switch. Such a move would be drastic, since I've successfully used Outlook .pst files as an archive for > 10 years.

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Re: switch
May 1, 2018 12:02AM PDT

Your choice, of course, to stay with Cox or switch to another email provider. Just 3 remarks:
1. If you can't send mails, strictly speaking it's not a pop3 issues, but a smtp issue.
2. You can keep using MS Outlook (any version) with any other email provider. So it's a less drastic move than you think.
3. Did you try (as an experiment, of course) another email client like Thunderbird, to see if that can send? If it can, you know it's a (setting?) issue in Outlook.

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Re: switch
May 1, 2018 8:26PM PDT

Thanks for your advice. Ironically, I'm dreading changing ISPs though COX's service has worsened steadily for some time. Facing a change of email address which I've had for 2+ decades seems daunting. It's used for both personal and professional contacts.

I agree that COX's smtp is the culprit, since all was well until about 10 days ago. No, I haven't tried another client such as Thunderbird since my email practices are deeply based on Outlook. However, COX's denial that the issue is not with their process - they conclude this since I can send/receive email via their dreadful webmail client - is motivation to move on.

I also was advised to try IMAP, which is easier to do than experiment with Thunderbird. My weekend computer work seems clear, though I hate spending so much time with this stuff. Bottom line: I'm a very senior computing professional who just wants to be a customer of personal computing.

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Re: change of email address
May 2, 2018 12:49AM PDT

That's daunting indeed. The best way to prevent it in the future is to buy your own domain (like lemaechmail.com) and host that with a provider where you can run an email server. I pay 18 euro (24 USD) for such a construct.

The three advantages:
1. It's independent of your ISP. You can change ISP's without changing email addresses.
2. It's independent of the hoster. You can move your domain to another hoster.
so it's a life-long address
3. You can make multiple addresses, even multiple inboxes, all within that same domain.