Dear All,

I'd really appreciate some help getting Outlook 2011 Mac to access an IMAP server. We recently moved our email to exchange on office365, but still have a couple of active mail addresses hosted externally which we need to access. Since we're using Outlook 2011 Mac as a client, we'd like to access the accounts through this program.

When I try to setup the IMAP account in Outlook (Version 14.4.3), I enter all the information from the ISP into the form. The status indicator remains orange. No error message is shown on the screen, and if I enable logging (http://technet.microsoft.com/en-us/library/jj984217(v=office.14).aspx), I also don't find any error messages.

I'm certain that I have the right account settings. The servers are on:

IMAP / SSL: port 993

SMTP: port 587 (TLS)

In outlook, I am inputting the following server information (screenshot attached):

User name: <user>

Password: <passwd>

Incoming server: <server> : 993

Override default port: not checked

Use SSL to connect (recommended): checked

Always use secure password: not checked

Outgoing server: <server> : 587

Override default port: checked

Use SSL to connect (recommended): checked

More Options:

Authentication: Use Incoming Server Info

I have no problem accessing the account through other clients (Mac Mail or an iPhone). On the same machine, I can connect manually to the IMAP server through the command line and connect manually to the SMTP server through the command line (redacted output below)

Is anyone able to help with a solution? Any suggestions would be very much appreciated!

Many thanks in advance,

Robert

IMAP

openssl s_client -connect <server>:993

CONNECTED(00000003)

depth=2 /C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Certification Authority

verify error:num=19:self signed certificate in certificate chain

verify return:0

---

Certificate chain

 0 s:/description=<XXXXX>/C=DE/ST=Hamburg/L=Hamburg/O=<XXXX>/CN=<XXXX>/emailAddress=<XXXX>

   i:/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Class 2 Primary Intermediate Server CA

 1 s:/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Class 2 Primary Intermediate Server CA

   i:/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Certification Authority

 2 s:/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Certification Authority

   i:/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Certification Authority

---

Server certificate

-----BEGIN CERTIFICATE-----

...

-----END CERTIFICATE-----

subject=/description=<XXXXX>/C=DE/ST=Hamburg/L=Hamburg/O=<XXXXX>/CN=<XXXXX>/emailAddress=<XXXXX>

issuer=/C=IL/O=StartCom Ltd./OU=Secure Digital Certificate Signing/CN=StartCom Class 2 Primary Intermediate Server CA

---

No client certificate CA names sent

---

SSL handshake has read 6053 bytes and written 328 bytes

---

New, TLSv1/SSLv3, Cipher is DHE-RSA-AES256-SHA

Server public key is 2048 bit

Secure Renegotiation IS supported

Compression: NONE

Expansion: NONE

SSL-Session:

    Protocol  : TLSv1

    Cipher    : DHE-RSA-AES256-SHA

    Session-ID: 9A04ED443ED9DA3E444F9DEB5B89E63603BBE07A7B5151350D0640D020BB73F8

    Session-ID-ctx: 

    Master-Key: <XXXXX>

    Key-Arg   : None

    Start Time: 1406103822

    Timeout   : 300 (sec)

    Verify return code: 0 (ok)

---

* OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE IDLE AUTH=PLAIN AUTH=LOGIN] Dovecot ready.

a login <user> <passwd>

a OK [CAPABILITY IMAP4rev1 LITERAL+ SASL-IR LOGIN-REFERRALS ID ENABLE IDLE SORT SORT=DISPLAY THREAD=REFERENCES THREAD=REFS THREAD=ORDEREDSUBJECT MULTIAPPEND UNSELECT CHILDREN NAMESPACE UIDPLUS LIST-EXTENDED I18NLEVEL=1 CONDSTORE QRESYNC ESEARCH ESORT SEARCHRES WITHIN CONTEXT=SEARCH LIST-STATUS SPECIAL-USE SEARCH=FUZZY QUOTA ACL RIGHTS=texk] Logged in

SMTP

swaks --tls --auth --to <recipient> --from <email> --server <server> 587

Username: <user>

Password: <passwd>

=== Trying <server>:25...

=== Connected to <server>.

<-  220 mx10.<server> ESMTP Exim Wed, 23 Jul 2014 10:34:53 +0200

 -> EHLO <computer>

<-  250-mx10.<server> Hello <address>

<-  250-SIZE 52428800

<-  250-EXPN

<-  250-PIPELINING

<-  250-STARTTLS

<-  250 HELP

 -> STARTTLS

<-  220 TLS go ahead

=== TLS started with cipher TLSv1:AES256-SHA:256

=== TLS no local certificate set

=== TLS peer DN="/description=<XXXX>/C=DE/ST=Hamburg/L=Hamburg/O=<XXXX>/CN=<XXXX>/emailAddress=<XXXX>"

 ~> EHLO <computer>

<~  250-mx10.<server> Hello <address>

<~  250-SIZE 52428800

<~  250-EXPN

<~  250-PIPELINING

<~  250-AUTH LOGIN PLAIN

<~  250 HELP

 ~> AUTH LOGIN

<~  334 VXNlcm5hbWU6

 ~> bGFycy56b2VsbG5lckBnYWlhY2FwaXRhbC5kZQ==

<~  334 UGFzc3dvcmQ6

 ~> d2l6YWVTdWc=

<~  235 Authentication succeeded

 ~> MAIL FROM:<email>

<~  250 OK

 ~> RCPT TO:<recipient>

<~  250 Accepted

 ~> DATA

<~  354 Enter message, ending with "." on a line by itself

 ~> Date: Wed, 23 Jul 2014 10:34:33 +0200

 ~> To: <recipient>

 ~> From: <email>

 ~> Subject: test Wed, 23 Jul 2014 10:34:33 +0200

 ~> X-Mailer: swaks v20130209.0 jetmore.org/john/code/swaks/

 ~> 

 ~> This is a test mailing

 ~> 

 ~> .

<~  250 OK id=1X9s0j-0005SK-LF

 ~> QUIT

<~  221 mx10.<server> closing connection

=== Connection closed with remote host.