smtp mail security - how do I setup this securely

Gallery URL = http://imagebank.typhoonhousewares.co.uk/main.php
Gallery version = 2.3 core 1.3.0
API = Core 7.54, Module 3.9, Theme 2.6, Embed 1.5
PHP version = 5.2.10 cgi-fcgi
Webserver = Microsoft-IIS/6.0
Database = mysqli 5.0.85-community-nt, lock.system=database
Toolkits = Exif, LinkItemToolkit, Thumbnail, ImageMagick, SquareThumb
Acceleration = none, none
Operating system = Windows NT INTRANET 5.2 build 3790
Default theme = matrix
gettext = enabled
Locale = en_GB
Browser = Mozilla/4.0 (compatible; MSIE 8.0; Windows NT 5.2; Trident/4.0; .NET CLR 1.1.4322; .NET CLR 2.0.50727; .NET CLR 3.0.4506.2152; .NET CLR 3.5.30729)
Rows in GalleryAccessMap table = 26
Rows in GalleryAccessSubscriberMap table = 933
Rows in GalleryUser table = 7
Rows in GalleryItem table = 931
Rows in GalleryAlbumItem table = 128
Rows in GalleryCacheMap table = 0

I need help with the SMTP mail security.

currently all is working even SMTP mail, but i had to configure the exchange 2003 server authentication as basic authentication (password sent in clear text), this makes the server very insecure.

1. can i set up the gallery2 smtp mail to be 'secure'??
2. how do i setup the gallery2 smtp mail to be secure??

i have searched the forums and only found a couple of non related articles.

thanks for the reply, I have just read through both the links, and neither seem to work;

just to double check;

1. edit the smtp.php file so that the line
list ($config['smtp.host'], $port) = array_merge(explode(':', $config['smtp.host']), array(25));
is changed to...
list ($config['smtp.host'], $port) = array_merge(explode('|', $config['smtp.host']), array(25));

2. change the email configuration, within General Admin Options, to the following
Server: tls://<address>|465
Username: <username>
Password: <password>
SMTP From Address: <email@address.com>

the credentials that I used for the above account information, does work when i remove tls security from the webserver, so i know this works, but when i modify it for tls/ssl security, if fails with the following error.

Error (ERROR_UNKNOWN) : Could not send mail to

in modules\core\classes\helpers\MailHelper_simple.class at line 93 (GalleryCoreApi::error)
in modules\core\classes\GalleryCoreApi.class at line 2844 (MailHelper_simple::sendTemplatedEmail)
in modules\core\AdminCore.inc at line 172 (GalleryCoreApi::sendTemplatedEmail)
in main.php at line 250 (AdminCoreController::handleRequest)
in main.php at line 104
in main.php at line 88
getParameter id.rootAlbum for core plugin
file_exists(C:\Inetpub\g2data\cache\module/core/0/0/0.inc)
--------------------------------------------------------------------------------
(mysqli):
SELECT
g2_PluginParameterMap.g_itemId,
g2_PluginParameterMap.g_parameterName,
g2_PluginParameterMap.g_parameterValue
FROM
g2_PluginParameterMap
WHERE
g2_PluginParameterMap.g_pluginType = 'module'
AND
g2_PluginParameterMap.g_pluginId = 'core'
AND
g2_PluginParameterMap.g_itemId = 0
--------------------------------------------------------------------------------

file_exists(C:\Inetpub\g2data\cache\module/core/0/0)
is_dir(C:\Inetpub\g2data\cache\module/core/0/0)
file_exists(C:\Inetpub\g2data\cache\module/core/0/0)
is_dir(C:\Inetpub\g2data\cache\module/core/0/0)
file_exists(C:\Inetpub\g2data\cache\module/core/0/0/0.inc)
rename(C:\Inetpub\g2data\cache\module\core\0\0\0.i26B.tmp,
C:\Inetpub\g2data\cache\module/core/0/0/0.inc)
file_exists(C:\Inetpub\g2data\cache\entity/0/0/7.inc)
getParameter default.theme for core plugin
Loading plugin matrix
Class not defined, trying to include it.
file_exists(C:\Inetpub\wwwroot\themes/matrix/theme.inc)
matrix plugin successfully instantiated
Check the version of the matrix plugin
file_exists(C:\Inetpub\g2data\cache\theme/_all/0/0/GalleryPluginHelper_fetchPluginStatus.inc)
The version of the matrix plugin is ok
file_exists(C:\Inetpub\g2data\smarty\templates_c\%%2202656580\matrix)
is_dir(C:\Inetpub\g2data\smarty\templates_c\%%2202656580\matrix)
file_exists(C:\Inetpub\g2data\smarty\templates_c\%%2202656580\matrix)
is_writeable(C:\Inetpub\g2data\smarty\templates_c\%%2202656580\matrix)
file_exists(C:\Inetpub\g2data\smarty\templates_c\%%2202656580\matrix/v_14)
getParameter id.rootAlbum for core plugin
getParameter default.theme for core plugin
Loading plugin matrix
matrix plugin successfully instantiated
Check the version of the matrix plugin
The version of the matrix plugin is ok
Loading plugin core
core plugin successfully instantiated
Check the version of the core plugin
The version of the core plugin is ok
is_readable(C:\Inetpub\wwwroot\modules\core\classes\helpers/../../../../themes/matrix/templates/core_1/local/EmailTest.tpl)
is_readable(C:\Inetpub\wwwroot\modules\core\classes\helpers/../../../../themes/matrix/templates/core_1/EmailTest.tpl)
is_readable(C:\Inetpub\wwwroot\modules\core\classes\helpers/../../../../modules/core/templates/local/EmailTest.tpl)
file_exists(C:\Inetpub\wwwroot\modules\core\classes\helpers/../../../../modules/core/templates/EmailTest.tpl)
stat(C:\Inetpub\wwwroot\modules\core\classes\helpers/../../../../modules/core/templates/EmailTest.tpl)
getParameter smtp.from for core plugin
mail(jfell@typhoonhousewares.com, Gallery Email Test, This is a test email
from Gallery2, Date: Wed, 09 Sep 2009 17:25:24 +0100
From:

Content-Type: text/plain; charset="utf-8"
)
realpath(C:\Inetpub\wwwroot\modules\core\classes/../../../)
realpath(C:\Inetpub\wwwroot/)
smtpmail error: Error (ERROR_PLATFORM_FAILURE) : Could not connect to smtp
host : 10060 : A connection attempt failed because the connected party did
not properly respond after a period of time, or established connection
failed because connected host has failed to respond.
in lib\smtp\smtp.php at line 71 (GalleryCoreApi::error)
in modules\core\classes\GalleryPlatform.class at line 1001
in modules\core\classes\helpers\MailHelper_simple.class at
line 90 (GalleryPlatform::mail)
in modules\core\classes\GalleryCoreApi.class at line 2844
(MailHelper_simple::sendTemplatedEmail)
in modules\core\AdminCore.inc at line 172
(GalleryCoreApi::sendTemplatedEmail)
in main.php at line 250 (AdminCoreController::handleRequest)

in main.php at line 104
in main.php at line 88
.......

Have I missed something??

regards
Jason