Wi fi issues with secure ports

[ANdy Jordan]

Hi guys,

Posting this under networking because I think that's likely the underlying issue but I have a very odd error that I can't resolve.

Starting yesterday I am getting 0X800CCC1A errors on outgoing email - your server does not support the connection encryption type you have specified. Setup is Outlook 2016 on Windows 10 connecting through wi-fi and my ISP to my own corporate domain with mail server hosted by Hostpapa. Setup hasn't changed for months and no previous issues have been experienced.

I have confirmed encryption details are correct on email setup - SSL through 465 for outgoing with all the rest of the stuff set up per Hostpapa and if I use my cell phone as a wireless hot spot or tethered connection I can send mail. That seems to rule out issues with my own setup and with Hostpapa. Incoming mail remains unaffected.

I have performed numerous reboots on the router and a factory reset without success. ISP has static IP and settings are correct - I should mention I am in Honduras so we aren't talking about a major player. I can't believe the ISP is blocking port 465 but when I telnet to it there is no response - I just get the command prompt after about a minute.

I'm starting to think I am going to have to get the ISP to try and investigate which is going to be an interesting challenge to say the least, but any ideas from the community as to what might be going on?

Thanks in advance for the help!

 

[sinisterDei]

I'm not sure it's you. I've just tried connecting to mail.papamail.net on port 465 and my connection is closed immediately. You can, however, use the non-SSL port 587 and it seems to connect fine.

 

[ANdy Jordan]

Interesting. I was originally told to configure for mail.mydomain.com which is generating the error on 465 and a 421 / 10060 (cannot connect) error on 587. Hostpapa just recommended I change to mail.papamail.net and I get rejected credentials on 465 for incoming and the same error as before on outgoing. 587 on mail.papamail.net is giving me the cannot connect error, with the same IP address as mail.mydomain.com.

There's definitely something 'weird' just not sure if it's my ISP (checked the router logs and while they aren't great they are showing ssmtp activity to the correct IP address in outgoing), or whether it's something about how my account is setup at Hostpapa. Thanks for trying!

 

[sinisterDei]

keep in mind, 587 is non-SSL.

 

[ANdy Jordan]

Right, changed encryption type - STARTTLS in the Outlook 2016 options.

 

[sinisterDei]

SSL/TLS may not be enabled at all on 587. Port 587 is just a renumber of port 25 because lots of ISPs block port 25. Do you need the encryption?

 

[ANdy Jordan]

Hostpapa states encryption is needed and with no encryption on 587 I get the cannot connect error. I'm wondering whether I am ever actually reaching the server.

 

[sinisterDei]

No clue then. Sorry!

 

[ANdy Jordan]

Thanks for the help it's appreciated!

 

[ANdy Jordan]

It just started working again - no changes made at my end, waiting to hear if Hostpapa did anything - very weird.