Problem with TLS and Outlook 2010

[Steffen Kaiser]

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On Thu, 11 Dec 2014, Wayne Andersen wrote:

> Log onto incoming mail server (IMAP): A secure connection to the server
> cannot be established.
>
> I have set the port to 143,993,995 none of them work, and the security to
> TLS.

993 is IMAP-over-SSL, which is probably not named "TLS", but "SSL" in 
Outlook.
Usually "TLS" means to use STARTTLS.
See: http://www.cs.umd.edu/faq/mailclient/outlook.html
But there are a lot of different Outlook versions and different names for 
settings.

> IMAP: 14:48:40 [db] srv_name = "mail.mydomain.com" srv_addr =
> 174.46.198.101:143

is this IP correct?

> IMAP: 14:48:40 [rx] * OK [CAPABILITY IMAP4REV1 LOGIN-REFERRALS IDLE
> AUTH=PLAIN AUTH=LOGIN] Dovecot ready.    ß----- not seeing the STARTTLS
> capability here.

Do you have a local Firewall or a Cisco-Router between this client and the 
server? Some firewalls filter out STARTTLS in order to scan the 
transferred content.

> C:\OpenSSL-Win64\bin>openssl.exe s_client -connect mail.mydomain.com:993
>
> verify error:num=20:unable to get local issuer certificate  ß--- Yes I see
> this and it may be an issue, but this certificate exist and is valid.

openssl does not guess certificates, you need to specify them on command 
line.

> ---
> From a linux client I get :
>
> * OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE IDLE
> STARTTLS AUTH=PLAIN AUTH=LOGIN] Dovecot ready.
>
> I do see STARTTLS  here.

does this client run in the same network as the windows client?

- -- 
Steffen Kaiser
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