diff --git a/src/pretix/base/services/mail.py b/src/pretix/base/services/mail.py
index dd5ab2378..875aed545 100644
--- a/src/pretix/base/services/mail.py
+++ b/src/pretix/base/services/mail.py
@@ -217,7 +217,7 @@ def mail(email: Union[str, Sequence[str]], subject: str, template: Union[str, La
                 for bcc_mail in settings_holder.settings.mail_bcc.split(','):
                     bcc.append(bcc_mail.strip())
 
-            if settings_holder.settings.mail_from not in (settings.DEFAULT_FROM_EMAIL, settings.MAIL_FROM_ORGANIZERS) \
+            if settings_holder.settings.mail_from in (settings.DEFAULT_FROM_EMAIL, settings.MAIL_FROM_ORGANIZERS) \
                     and settings_holder.settings.contact_mail and not headers.get('Reply-To'):
                 headers['Reply-To'] = settings_holder.settings.contact_mail