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Home » Kerio User Forums » Kerio Connect » KOC Secure SMTP via SSL does not work (confirmed)
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hh371

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Can anyone confirm that they have the outlook connector working via SSL for SMTP (outbound) email? This would be Secure SMTP service on port 465 (or other). Can you also confirm that it works when regular, insecure SMTP (port 25) is disabled at the same time? You would have to send a message internally to test this. I'm guessing no on can confirm this because KOC doesn't actually work with SSL for Secure SMTP...

I have done a bunch of troubleshooting and have come to the conclusion that KOC cannot sent mail from outlook to the mailserver via SSL SMTP. Furthermore, the setting within the outlook connecter that allows you to check the box for a "Secure Connection (SSL)" is misleading. The IMAP connector in KOC works via SSL, but SMTP does not work with SSL

(And no, I don't have a personal firewall or anti-virus blocking the port...so please don't go that route.)

Here is all the proof you need.

#1
I use Thunderbird all the time with SSL for Secure IMAP and Secure SMTP to send/receive messages on my mailserver. Never had a problem.

#2
I setup port 26 on the mailserver for regular SMTP. Also disabled Secure SMTP on the mailserver. Configure Outlook accordingly. I was able to successfully sent an email message via KOC with the "Secure Connection (SSL)" check box enabled...(further proof that this setting is misleading since my Secure SMTP service was disabled).

#3
I disabled port 26 on the mailserver for regular SMTP (restarted). Then, I enabled port 26 under Secure SMTP (restarted). I attempted to send a message via KOC, but was unsecessful. Got the same old "0x80042109 cannot connect to SMTP server" error as always.

Network communication is not my problem. All the firewalls are down in front of the server. The test workstation is a fresh install running only XP, Office and KOC. The version of the mailserver and KOC are the same (6.4). And again, Thunderbird works just fine with SSL connections.

I believe this pretty much proves that KOC doesn't work with Secure SMTP via SSL. The KOC setting in outlook should have three check boxes for "Secure Connection (SSL)". One check box next to IMAP, SMTP and HTTP...instead of only one that misleads end users into believing it covers all three.

[Updated on: Sat, 02 June 2007 06:57]

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Pavel Dobry (Kerio)

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It was already discussed several times in this forum.
KOC (as well as Outlook with POP3 or IMAP account) does not use SMTPS on port 465. It is using TLS over standard SMTP on port 25 (STARTTLS command). It represents same level of security as SMTPS.
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