Email sent from any wesleyan address to yahoo.com addresses may be significantly delayed or automatically flagged as spam. The wesleyan.edu domain has been greylisted due to a series of mass student mailings that were marked spam by wesleyan students who get their mail forwarded to yahoo.
If you’re sending an important email to someone who uses yahoo, for now you should send it from somewhere besides wesleyan webmail.
I will refrain from making any snide comments about this situation, even though it would extremely easy. Thanks for the info, faithful sys-admin, and good luck convincing staff not to send unsolicited mail!