Hello Stavros, I'm not sure I understand. Could you go into more detail?

*In all seriousness though (lol): You could have different types of personalities, depending on the email address of the person who doesn't want the spam. Like someone pretending mnesty.com is their work address but is still treating it like a personal message. That way the spammer will disregard the fact that the reply email isn't the same as the original. EDIT: Nevermind, I see you said you did that already... I think. ... Help?

It's too hard to write generalities, I'm afraid. You can only write about 10 different sentences before you start to repeat yourself (or at least I can't do it). Feel free to send me sentences for me to add!

This is amazing. Looping in my supervisor. [add a second email agent to thread. The two email agents will fork the email chain for the spammer and ask similar questions, hopefully wasting more of their time.

I'm so sorry, but I think I lost my whole inbox. Could you please send me a recap of our whole conversation? [sent with the original seed email as body]

True, it is tricky. But it'd be a fun exercise. I suppose it's an exercise in dark humor... hm...

"Hey, I'm switching to my work email. Refresh me on the details again." "I'll have to get back with you. Can you repost a summary?" "I'm sorry, but your emails are hard to read. Could you format them alittle nicer. Thanks!" "Gee, I'd love to help. It's hard to think of how, though."

What you really need to take this to the next level is to be able to crowd source some content. Maybe check if you have a response that you think will work and that you haven't used yet and if not ask a pool of users for suggestions. You could use the fork suggestion above to do some testing among the proposed responses.

Have you considered word replacement lists? Like for "This looks really cool", "This looks really[cool, great, awesome, other synonym]". Might string people along longer.