Outlook vs Thunderbird (re disabling SSL)

[Sam Kuper]

On Wed, Jul 08, 2020 at 12:05:55PM +1000, Mark Constable wrote:
> I spent a week trying every cypher combination I could find via Google
> for Dovecot but with the phone going off the hook from complaints by
> customers not being able to pick up their mail. We had to respond with
> some solution so, after a week, disabling SSL was very reluctantly the
> only option left. We lost ~40 customers to outlook.com because of
> this.

Ouch.  But does outlook.com not require TLS?  (I don't currently have an
outlook.com account.)

If so, then why would customers be able to solve their problem by moving
to outlook.com?  Maybe by using outlook.com's webmail interface, I
guess, but you could presumably compete with this by offering
Squirrelmail or Roundcube.

Yet another possible workaround for customers using email clients or
operating systems that don't speak recent versions of TLS is to have
them install stunnel on their PC, or else to send them a box (e.g.
Raspberry Pi) running stunnel that they can put on their LAN/WLAN:

https://joewein.net/blog/2018/07/04/outlook-express-error-0x800ccc0b-and-the-end-of-tls-1-0-deprecated-ssl-protocol/

https://en.wikipedia.org/wiki/Stunnel

Of course, the main problem with sending a box is that it would
periodically require software updates & reboots.  If you already have a
routine for upgrading software on boxes on customer premises, then
include the boxes in that routine; otherwise, it's a headache.

Also, the stunnel approach would not help for non-jailbroken iOS devices
except while they are downstream of an stunnel box.  So, OK over the
WLAN but no good while on mobile data.

Anyway, good luck!

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