I noticed in my emails from here that the DKIM and SPF records in DNS are not set up:
Received-SPF: permerror (google.com: permanent error in processing during lookup of bootstrapped@userscape.com) client-ip=64.71.148.3;
Authentication-Results: mx.google.com;
spf=permerror (google.com: permanent error in processing during lookup of bootstrapped@userscape.com) smtp.mail=bootstrapped@userscape.com;
dkim=temperror (no key for signature) header.i=@
This means you need to add those DKIM and SPF records for the userscape.com domain since that’s the return email address.
https://meta.discourse.org/t/configure-your-domain-for-discourse-hosted-email/14177
If you’d rather set it up on the bootstrapped.fm domain then change the return email in site settings to noreply@bootstrapped.fm
or similar.
If you need any assistance with this let me know!