[stunnel-users] Outlook has problems with sending email

Kenneth Simpson ken at VirtualMachines.COM
Wed Oct 27 00:54:28 CEST 2004

Hi - I'm having problems with Stunnel 4.05 and Outlook - but not with

Unfortantely, most of our users use Outlook from Office 2000 and Office XP.

The problem is Outlook can't send email when using SIMAP/SSMTP. If the 
users set their SMTP server to be their ISP, then Outlook doesn't have a 

It suggests a sendmail issue except Mozilla/Thunderbird work fine.

How do most people configure stunnel for Outlook?

We're behind a screening router and port 587 - the so-called sendmail
"submission" port - is currently closed. All ICMP is administratively
disabled for this host at the router.

But sendmail on this particular host is configured for port 587 behind
the firewall.

Is there a need to configure stunnel for port 587 too?

We're using

        OpenSSL 0.9.7d
        Sendmail 8.12.10
        Stunnel 4.0.5
        SPARC Solaris 5.8

Enclosed is the stunnel.conf file.

Under version 3.x roughly year ago things appeared to be working
correctly - but we've upgraded both sendmail and SSL since then -
and our users where migrating from Outlook Express to Outlook.

Any ideas?

I've added the options

        TIMEOUTbusy  = 300
        TIMEOUTclose = 60
        TIMEOUTidle  = 43200

but no help.

Any help would greatly appreciated!

-- Ken

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