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Ran into same issue. What worked was the first email that gives you a link to gumroad. After using the coupon and providing an email to gumroad, it showed me the confirmation page, but didn't send me an email for the PDF. The fix was to go to that gumroad confirmation page, and where it says "enter a password" (basically it'll create a gumroad account) you'll then be able to login and check your gumroad account, book should be there.

Ouch. Feel free to email me on this [1] email address and I’ll help sort it out.

Gumroad has fraud protection for free “purchases” as well and I’m also filtering out domains that are known to have high bounce rates or not valid domains.

[1] https://blog.pragmaticengineer.com/connect/

still having issues. got a second email in gmail that appears to be a copy of the first email. the pain never ends.

That sounds weird. I won't refute, because I used a Google Accounts email (albeit with my own domain). But what makes you say that?

I used a personal domain email (non-Gmail) and everything went smoothly for me.

Same issue for me. Just emailed you. Thx