>> Just deny anonymous email on 587.
>> I've never seen a spammer touch 587 though.

> Hmmm... good idea.  Although I'm not sure if my MTA allows for that.  Will 
> have to look into it.  More importantly though, I don't know how easily it 
> will be to convince all my users to reconfigure their clients (esp. the PC 
> illiterate ones).

I went through something similar a long time ago...

1. Get encrypted connections working first, alongside non-encrypted 
ones, so that they both work.

2. Write up and send out dummy-proof step-by-step instructions for the 
most popular mail clients, and then send out warning emails to everyone 
that will be affected, explaining what you are doing and why (in 
layman's terms, of course), and set a deadline when you will be 
terminating the non-encrypted connection support.

3. Make the changes yourself to any/all computers that are local to you 
that are used by any management types. Be sure to explain in person to 
these people what/why you are doing, ask them about what they use to 
access email from the outside, and hand them a printed copy of the 
instructions for their client - or, prepare instructions for their 
client if it is one that you hadn't already prepared instructions for.

4. Give everyone a cell/home phone number they can reach you at for when 
they can't figure out your dummy-proof instructions...

5. Send out warnings 3 days before terminating the non-encrypted 
connection support.

6. Send out a final warning the day before.

7. Terminate non-encrypted connections.

8. Answer an un-ending series of help calls when people call screaming 
that they cannot access their email, and be prepared for the names they 
will call you for daring to do something like this without any warning.

-- 

Best regards,

Charles

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