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Editorial Team
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Asked: 2026-05-26T18:23:04+00:00

I keep getting a NO LOGIN failed message when trying to connect to the

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I keep getting a NO LOGIN failed message when trying to connect to the Exchange server using Mail::IMAPClient. From what I’ve read everything should work. I’ve gotten it to connect to Gmail but trying to connect to MS Exchange is more difficult it seems like. What could be causing it to fail on authenticating?

use strict;
use warnings;
use Authen::NTLM;
use Mail::IMAPClient;

## Option variables
my $debug 
my $authmech = "NTLM";
my $username = "useraccount";
my $password = "set by prompt";

## Settings for connecting to IMAP server
my $imap = Mail::IMAPClient->new(
    Server            => 'mail.server.domain',
    User              => $username,
    Password         => $password,
    Port              => 993,
    Ssl                => 1,
    Authmechanism  => $authmech,
    Debug => 1
) or die "Cannot connect through IMAPClient: $@\n";

The out put from running the script.

~]./status_page_msg.pl -d

Logging in as : user_account

Started at Sat Nov 12 19:20:11 2011
Using Mail::IMAPClient version 3.29 on perl 5.008008
Connecting via IO::Socket::SSL to mail.server.domain:993 Timeout 600
Connected to mail.server.domain
Read:   * OK The Microsoft Exchange IMAP4 service is ready - 'serverName'
Sending: 1 AUTHENTICATE NTLM
Sent 21 bytes
Read:   +
Sending: TlRMTVNTUAABAAAAB6IAAAoACgAgAAAAAAAAAAoAAABlYW0tc3RhdHVz
Sent 58 bytes
Read:   1 NO AUTHENTICATE failed.
ERROR: 1 NO AUTHENTICATE failed. at /usr/lib/perl5/site_perl/5.8.8/Mail/IMAPClient.pm line 3047
        Mail::IMAPClient::authenticate('Mail::IMAPClient=HASH(0x1ac95440)', 'NTLM', 'undef') called at /usr/lib/perl5/site_perl/5.8.8/Mail/IMAPClient.pm line 443
        Mail::IMAPClient::login('Mail::IMAPClient=HASH(0x1ac95440)') called at /usr/lib/perl5/site_perl/5.8.8/Mail/IMAPClient.pm line 395
        Mail::IMAPClient::Socket('Mail::IMAPClient=HASH(0x1ac95440)', 'IO::Socket::SSL=GLOB(0x1b43e110)') called at /usr/lib/perl5/site_perl/5.8.8/Mail/IMAPClient.pm line 351
        Mail::IMAPClient::connect('Mail::IMAPClient=HASH(0x1ac95440)') called at /usr/lib/perl5/site_perl/5.8.8/Mail/IMAPClient.pm line 307
        Mail::IMAPClient::new('Mail::IMAPClient', 'Server', 'mail.server.domain', 'User', 'user_account', 'Password', 'Correct', 'Port', 993, ...) called at ./status_page_msg.pl line 63
Cannot connect through IMAPClient: 1 NO AUTHENTICATE failed.
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1 Answer

  1. Editorial Team

    You should have said that it used to work, but stopped working when the server was upgraded to Exchange 2010.

    A quick Google for "Exchange 2010 NTLM IMAP" turned up Discontinued Features from Exchange 2007 to Exchange 2010:

    NTLM isn’t supported for POP3 or IMAP4 client connectivity in Exchange 2010 RTM. Connections from POP3 or IMAP4 client programs using NTLM will fail. If you are running Exchange 2010 RTM, the recommended POP3 and IMAP4 setting alternatives to NTLM are:

    • Kerberos (GSSAPI)
    • Plain Text Authentication with SSL

    If you are using Exchange 2010 RTM, to use NTLM, you must retain an Exchange 2003 or Exchange 2007 server in your Exchange 2010 organization.

    Support for NTLM authentication for POP3 and IMAP4 connectivity has been brought back in Exchange 2010 SP1.

    Since you’re using SSL, you should be able to switch to plain text authentication (just delete Authmechanism). Or, get your sysadmins to install SP1.

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