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Outlook won't send POP3 mail via Outlook.com; "server does not support encryption type." No port/encryption combinations work. Other POP3 accounts fine.

Outlook 2007 suddenly stopped sending POP3 mail via Outlook.com. Error message is: "Your server does not support the connection encryption type you have specified."

--Sending was set to 587/TSL. Changing to 465/SSL didn't help. Also tried "auto" & "none" on both ports. Same error.

--Very short messages & simple messages [no graphics], & some forwards, are sent instantly. Longer/graphic messages invariably fail.

--Moved server timeout to 1.5 minutes. No help.

--Unchecked "server requires encrypted connection." No help.

--Unchecked "outgoing server requires authentication." No help.

--Inbound port is 995 encrypted. [Have also tried 110 unencrypted.]

>>>I have 10 other POP3 accounts using the same Outlook inbox, & all work fine.

Problem onset MAY have been coincident with a bunch of MS updates last week, but I can't be sure [I've tried uninstalling a few; no success].

I'm running Win 7 Pro.

All help welcome except suggestions that I switch to IMAP. Thanks.

Daniel Booker

Try this in your account settings.

Incoming mail server: pop3.live.com
Outgoing mail server (SMTP): smtp.live.com

Logon Information: (Going to assume you have not changed your information so don't have to worry about this, but just in case.)
User Name: your @outlook.com email address
Password: your @outlook.com password

Then click on the “More Settings” button:
Outgoing Server tab: mark the box “My outgoing server (SMTP) requires authentication” and select “use same settings as my incoming mail server”.

Advanced tab – Server Port Numbers:
Incoming server (POP3): port 995 – you must also mark the box “this server requires an encrypted connection (SSL)”
Outgoing server (SMTP): port 587 – you must also choose “TLS” for the option “Use the following types of encrypted connection”.

jamesport

ASKER

Thanks, but those were my exact settings when it failed...& in place now.

[Sorry about the "TSL" typo above; I meant TLS]

Daniel Booker

If you can log into the webmail just fine and it is only this 1 account in Outlook. I would try removing the account and adding it back.

jamesport

ASKER

Good suggestion. Removed problem account, closed Outlook, restarted...same problem.

Just in case, I ran scanpst on my data file. No help.

Daniel Booker

Sorry, out of ideas now :(

jamesport

ASKER

Have been logging Outlook ops in hope of finding solution. Here's the latest failure to send:

2015.03.24 12:36:57 LIVE: ReportStatus: RSF_COMPLETED, hr = 0x00000000
2015.03.24 12:36:57 LIVE: Synch operation completed
2015.03.24 12:37:30 LIVE: Synch operation started (flags = 00000001)
2015.03.24 12:37:30 LIVE: UploadItems: 1 messages to send
2015.03.24 12:37:30 SMTP (smtp.live.com): Begin execution
2015.03.24 12:37:30 SMTP (smtp.live.com): Port: 587, Secure: TLS, SPA: no
2015.03.24 12:37:30 SMTP (smtp.live.com): Finding host
2015.03.24 12:37:30 SMTP (smtp.live.com): Connecting to host
2015.03.24 12:37:30 SMTP (smtp.live.com): Connected to host
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 220 BLU436-SMTP155.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 24 Mar 2015 09:37:42 -0700
2015.03.24 12:37:30 SMTP (smtp.live.com): [tx] EHLO LPS
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-BLU436-SMTP155.smtp.hotmail.com Hello [207.38.131.71]
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-TURN
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-SIZE 41943040
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-ETRN
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-PIPELINING
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-DSN
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-ENHANCEDSTATUSCODES
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-8bitmime
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-VRFY
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-AUTH LOGIN PLAIN XOAUTH2
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250-OK
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 250 STARTTLS
2015.03.24 12:37:30 SMTP (smtp.live.com): Securing connection
2015.03.24 12:37:30 SMTP (smtp.live.com): [tx] STARTTLS
2015.03.24 12:37:30 SMTP (smtp.live.com): <rx> 220 OK
2015.03.24 12:37:30 SMTP (smtp.live.com): Securing connection
2015.03.24 12:37:30 SMTP (smtp.live.com): Disconnected from host
2015.03.24 12:37:30 SMTP (smtp.live.com): End execution
2015.03.24 12:37:30 LIVE: ReportStatus: RSF_COMPLETED, hr = 0x800ccc1a
2015.03.24 12:37:30 LIVE: Synch operation completed

jamesport

ASKER

UPDATE

Desperate, I switched to port 25 unencrypted, & it's working.

I'll use this way for now, but really need help getting back to one of the encrypted ports.

Thanks.

ASKER CERTIFIED SOLUTION

Rob

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Outlook won't send POP3 mail via Outlook.com; &quot;server does not support encryption type.&quot; No port/encryption combinations work. Other POP3 accounts fine.

Outlook won't send POP3 mail via Outlook.com; "server does not support encryption type." No port/encryption combinations work. Other POP3 accounts fine.