Outlook With FreeBSD IMAP

I am using the default FreeBSD IMAP server in FreeBSD.  It
works great 
with thunderbird, but Outlook is not able to log in even
though I have 
Secure Authentication checked.  Any ideas?


-- 
Chris Maness
(909) 223-9179
http://www.chrismaness.com


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On 2/26/07, Chris Maness <chrischrismaness.com> wrote:
> I am using the default FreeBSD IMAP server in FreeBSD. 
It works great
> with thunderbird, but Outlook is not able to log in
even though I have
> Secure Authentication checked.  Any ideas?

Do you mean Secure Password Authentication or SPA? Don't use
that, as
it's a Microsoft proprietary authentication method.


-- 
Juha
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.nz/juha
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Juha Saarinen wrote:
> On 2/26/07, Chris Maness <chrischrismaness.com> wrote:
>> I am using the default FreeBSD IMAP server in
FreeBSD.  It works great
>> with thunderbird, but Outlook is not able to log in
even though I have
>> Secure Authentication checked.  Any ideas?
>
> Do you mean Secure Password Authentication or SPA?
Don't use that, as
> it's a Microsoft proprietary authentication method.
>
>
How do I use the Cram-MD5 passwords with Outlook?  Or do I
have to go 
plain text?

Thanks,

-- 
Chris Maness
(909) 223-9179
http://www.chrismaness.com


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> I am using the default FreeBSD IMAP server in FreeBSD. 
It works great with

what's the default FreeBSD IMAP server? i don't remember
IMAP in base 
FreeBSD distro?


> thunderbird, but Outlook is not able to log in even
though I have Secure 
> Authentication checked.  Any ideas?

no idea. with dovecot all imap clients work, both with and
without 
ssl.

anyway - outlook doesn't work well anytime, especially with
imap. simply 
don't use it, thunderbird for windows works good with imap.
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> *Not* off-topic, the context being how best to
configure Outlook
> for use with FreeBSD IMAP.  One hopes something more
secure than
> plain-text passwords can be made to work.
>
> My answer is "Don't use Outlook.  For anything. 
Period."

as my answer. i have ca 500 users in my networks (mostly
one), outlook 
users always have "problems", and i always answer
that they like problems 
and use outlook.
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> anyway - outlook doesn't work well anytime, especially
with imap. simply 
> don't use it, thunderbird for windows works good with
imap.

This is not as feasible as stated. Changing 500 users from
Outlook to 
something they have likely never seen is always a nightmare,
even if the 
subtleties are small.

Try explaining that to upper management..."uh, we are
getting rid of 
your Outlook, as well as everyone elses because our server
won't work 
with it. It should only take an hour per user to transfer
everything 
over to the new software, and most users will experience
data loss 
because not all parts are transferable." In short, it
would cost less to 
install Exchange than it would to migrate, train and
re-create data for 
that many users.

To the OP...have you checked the log files on the server to
check for 
errors? I have numerous Outlook and OE users who use IMAP
over SSL, and 
SMTP Auth on port 587 (again with SSL). We do not use SPA.
We use 
courier-imap and qmail, and have vpopmail managing the
multiple domains.

Almost all of our domains have to use their full email
address as 
username. I have seen before however, that sometimes Outlook
will try to 
append their domain to the username (eg: userdomain.comMSdomain or 
something similar) so the problem may rest there.

Depending on what IMAP server you use, the log file may be 
/var/log/maillog. It should give you an idea of where to
start looking.

Steve

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In response to Steve Bertrand <iaccountsibctech.ca>:

> > anyway - outlook doesn't work well anytime,
especially with imap. simply 
> > don't use it, thunderbird for windows works good
with imap.

I've got to say, I don't know where this is coming from.

We have a menagerie of IMAP clients here, and probably 10%
of them are
Outlook, and we don't have any more trouble with the Outlook
clients than
any other clients.

We use Cyrus.  Perhaps that's saying something in Cyrus'
favor?

-- 
Bill Moran
Collaborative Fusion Inc.
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>> > How do I use the Cram-MD5 passwords with
Outlook?
>> > Or do I have to go plain text?
>>
>> Off-topic for FreeBSD-Questions but I don't
believe
>> Outlook supports CRAM-MD5 out of the box.
>
> *Not* off-topic, the context being how best to
configure Outlook
> for use with FreeBSD IMAP.  One hopes something more
secure than
> plain-text passwords can be made to work.
>
> My answer is "Don't use Outlook.  For anything. 
Period."
> but the OP may be stuck with it for some reason.
>

Thank You, if I was talking about Anna Nichole Smith or
something, that
would be *OFF* topic. ;o).

I am stuck with outlook if I want to synch my PDA phone to
my e-mail.  It
seems to work ok with gmail pop3.  Maybe I can just have
sendmail foreward
a copy of all my mail to gmail.

Thanks Guys,

Chris Maness


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On Mon, Feb 26, 2007 at 07:16:58AM -0800, chrischrismaness.com wrote:
> >> > How do I use the Cram-MD5 passwords with
Outlook?
> >> > Or do I have to go plain text?
> >>
> >> Off-topic for FreeBSD-Questions but I don't
believe
> >> Outlook supports CRAM-MD5 out of the box.
> >
> > *Not* off-topic, the context being how best to
configure Outlook
> > for use with FreeBSD IMAP.  One hopes something
more secure than
> > plain-text passwords can be made to work.
> >
> > My answer is "Don't use Outlook.  For
anything.  Period."
> > but the OP may be stuck with it for some reason.
> >
> 
> Thank You, if I was talking about Anna Nichole Smith or
something, that
> would be *OFF* topic. ;o).
> 
> I am stuck with outlook if I want to synch my PDA phone
to my e-mail.  It
> seems to work ok with gmail pop3.  Maybe I can just
have sendmail foreward
> a copy of all my mail to gmail.
> 
> Thanks Guys,
> 
> Chris Maness

I run imap-uw. Outlook 2003 works just fine with my mail
server. However, I
haven't been able to get Outlook 2002 to work properly.
Outlook Express also
works fine for me.

My (quite popular) page about running both sendmail and
imap-uw with SSL/TLS
and authentication can be found here:
<http://www.puresimplicity.net/~hemi/freebsd/sendma
il.html>. The page states
that one of the goals of the described mail setup is
compatibility with
Microsoft e-mail clients.

Thanks,

Josh
-- 
Josh Tolbert
hemipuresimplicity.net  ||  http://www.pures
implicity.net/~hemi/

Security is mostly a superstition. It does not exist in
nature, nor
do the children of men as a whole experience it. Avoiding
danger
is no safer in the long run than outright exposure. Life is
either
a daring adventure, or nothing.
    -- Helen Keller
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--On Monday, February 26, 2007 21:55:45 +1300 Juha Saarinen

<juhasaarinengmail.com> wrote:

> On 2/26/07, perryhpluto.rain.com <perryhpluto.rain.com> wrote:
>> *Not* off-topic, the context being how best to
configure Outlook
>> for use with FreeBSD IMAP.  One hopes something
more secure than
>> plain-text passwords can be made to work.
>
> Uh, OK.
>
>> My answer is "Don't use Outlook.  For
anything.  Period."
>> but the OP may be stuck with it for some reason.
>
> Outlook supports SSL and TLS for both IMAP and SMTP if
makes a
> difference, plus AUTH but I'm not sure if it sets up a
tunnel before
> sending the plain-text password. Googling seems to
indicate otherwise,
> but perhaps someone better versed in Outlook can say
for sure?

Outlook works just like any other IMAP client.  You can set
up SSL or TLS. 
You can change the default port, if you need to.  And yes,
it sets up the 
tunnel before exchanging credentials and connecting to one's
mailbox.

I don't think there's any way to use CRAMD5, but why would
you need to if 
you're already using SSL?

Paul Schmehl (paulsutdallas.edu)
Senior Information Security Analyst
The University of Texas at Dallas
http://www.utdal
las.edu/ir/security/