[SOLVED] connecting to zarafa via imap using outlook

[zippydan]

I can succesfully connect to incoming IMAP server and send test message.  But ONLY with encryption off.  I cannot use TLS or SSL.  I can only connect on port 143 with encryption off.  Port 993 fails even though it should be open in the packet filter (under mail reception service) and IMAPS is enabled under Groupware and IMAP is enabled under the user account.

I can successfully connect to outgoing SMTP server but I CANNOT send a test message.  Furthermore, I CANNOT connect with encryption off or with SSL, ONLY with TLS.  But no matter what I do, it keeps asking me for a password!!

Why won't it authenticate on the outgoing side when it authenticates fine incoming with the same user and password?  Why can't I use encryption on the incoming side?

[christian]

I'm not sure you are not mixing up multiple points.

1 - What's your concern about SSL vs. TLS?
Are you thinking that SSL provides encryption and TLS doesn't?

2 - for what concerns authentication, I'm not 100% sure Zarafa is using same login as compared to standard IMAP server (in Zentyal implementation)
in order to authenticate while using stand IMAP and SMTP server, you must use your email address while (to be checked) Zarafa may rely on your uid (login)

As IMAP is used to read received messages and SMTP is used to send messages, this may explain why you face such behaviour.

[zippydan]

Ok, I solved the SMTP problem.  First, you MUST list your user's DEFAULT mailbox address under User Information.  DO NOT use any alias addresses.  Secondly, SMTP is authenticated using your default mailbox address as well and that MUST match the address you entered earlier.

Now, onto the incoming IMAP server.  I do not care if I connect with SSL or TLS, but I do want to connect with encryption.  Zarafa's incoming IMAP authenticates using your user ID (uid) and NOT with your mailbox address.  I've already got that part as I can authenticate just fine with IMAP.  BUT ONLY WITH ENCRYPTION OFF.  As soon as I select SSL or TLS for my incoming IMAP connection, the connection is immediately rejected.

In summary,
outgoing authentication is fine with TLS on.
incoming authentication is fine ONLY with encryption OFF.

I want encryption on the incoming side.

[christian]

I can't really help with the Zarafa side therefore with IMAP. I suppose you have to enable TLS or SSL support at Zarafa level.
If done, then check that:
- it doesn't conflict with IMAP defined in standard mail service
- firewall permits access on ports you've selected for IMAP(S)

[zippydan]

After looking at /var/log/zarafa/gateway.log and googling the error messages there, I think I found my answer:

https://forums.zarafa.com/showthread.php?8792-Outlook-2010-IMAPs-and-sslv2

Basically it looks like Microsoft is incompatible with Zarafa's IMAPs server using SSLv3 or TLSv1.  It is unclear if this is a bug on Microsoft's side or on Zarafa's side.