'i wont accept a pdf attachment from you because youre a redteamer and you might try to hack me' isnt the galaxy brain defensive secuity posture that you think it is
@Viss "i deleted your email because you're the security guy and might phish me"
I'd just attach each page as an 1100x850 monochrome .GIF named with the page numbers instead. 
If they complain, put the images in a .ZIP and attach that instead. 
@VictimOfSimony meh. i just said 'look if you dont trust me theres no reason to bother'
@schrotthaufen ive learned to take the 'look if you dont trust me to send you a pdf, theres no reason to bother' approach.
@schrotthaufen its been a while since the last time someone said some shit like that, but its so incredibly tiresome. its literally saying "i dont trust you to send me an email attachment because im afraid you might hack me"
which is the problem.
this completely random, unprovoked distrust for no explainable reason.
why continue anything with that person ever again? its always going to be an uphill battle and its always going to mean having to jump through hoops to prove honesty forever.
@Viss @VictimOfSimony That's how I deal with it.
We're SysAdmins (among other things). They sort of Have to trust me (us).
But here's the thing: I've noticed that those people think Very Highly of themselves (they're important enough to bother to hack ... lol, no).
And also, I have time, motivation, or interest in hacking them (lol, no).
@elfin @VictimOfSimony this guy works at google and is on one of their security teams, so its extra tiresome