Tutorial for setting up MS Office 2003 Outlook 2003 for personal Google Email Accounts in 2021

[Lawrence Aracabia]

First I tried to set up Win10 Outlook 2003 as per these (older) tutorials.
https://cs.thomsonreuters.com/ua/webbuild/cs_us_en/email/setup_outlook_2003_gmail_imap.htm
https://techieinspire.com/step-by-step-how-to-add-gmail-to-outlook-2003-or-outlook-2007/

The incoming IMAP server setups documented in those two older references
worked with my Google Account which does not have 2FA (two factor
authorization) or 2SV (two step verification) or OAUTH2 turned on.
https://myaccount.google.com/security

I don't know if it matters but I had long ago also turned on "Less secure
app access" in my Google Account (in order for Thunderbird to work).

Following those two older tutorials, I was able to receive email through
IMAP between Outlook 2003 and the Google IMAP servers, but sending email
through Google SMTP servers came up with this enryption error.
https://i.postimg.cc/vTHgvmbC/Screenshot-95.jpg
Task 'smtp.gmail.com - Sending' reported error (0x800CCC7D) : 'Your
outgoing (SMTP) server does not support SSL-secured connections. If
SSL-secured connections have worked in the past, contact your server
administrator or Internet service provider (ISP).'

My original Outlook 2003 email settings were
Incoming mail server = imap.gmail.com, port 993, use SSL encryption.
Outgoing mail server = smtp.gmail.com, port 587, use SSL encryption.

The problem turned out to be that Outlook doesn't support TLS encryption
coupled with the Google SMTP server requirement for TLS encryption.

To add TLS encryption, I installed Stunnel which came with a default
configuration file that I kept even as I'm onlyl using the IMAP section.
[gmail-pop3]
client = yes
accept = 127.0.0.1:110
connect = pop.gmail.com:995
verifyChain = yes
CAfile = ca-certs.pem
checkHost = pop.gmail.com
OCSPaia = yes

[gmail-imap]
client = yes
accept = 127.0.0.1:143
connect = imap.gmail.com:993
verifyChain = yes
CAfile = ca-certs.pem
checkHost = imap.gmail.com
OCSPaia = yes

[gmail-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.gmail.com
OCSPaia = yes

My original Outlook 2003 email settings were then modified to
Incoming mail server = imap.gmail.com, port 993, use SSL encryption.
Outgoing mail server = 127.0.0.1, port 25, do not use SSL encryption.

Given my only problem was in sending email through Google smtp servers, the
only setting I changed from those older web tutorials was to change the
Outlook 2003 SMTP outgoing server and port from "smtp.gmail.com" & "587" to
127.0.0.1" & "25" and I turned off the outgoing SMTP SSL checkbox.

This was done inside of Outlook 2003 only.
There was no need to touch anything in the Google Account settings.

It may be important to point out that I do not have OAuth turned on in my
Google Account, nor do I have 2SV or 2FA turned on, but that I do have
"Less secure app access" turned on (for Thunderbird to work on Windows 10).

If you want to test this procedure, you can get Outlook 2003 over here.
https://archive.org/details/Office03EDU
Product key P8Y83-VVB86-8Y2YF-XPRCB-KXD63
Identifier Office03EDU, Upc 805529996892