Research has found people underestimate the likelihood strangers will comply with their direct requests (Bohns, 2016; Flynn & Lake, 2008). Here we argue this “underestimation- of-compliance effect” may be limited to requests made face-to-face. We find when making direct requests over email, requesters instead overestimate compliance. In two studies, participants asked strangers to comply with requests either face-to-face or over email. Before making these requests, requesters estimated the number of people they expected to say “yes”. While requesters underestimated compliance in face-to-face contexts, replicating previous research, they overestimated compliance in email contexts. Analyses of several theorized mechanisms for this finding suggest that requesters, anchored on their own perspectives, fail to appreciate the suspicion, and resulting lack of empathy, with which targets view email requests from strangers. Given the prevalence of email and text-based communication, this is an extremely important moderator of the underestimation-of-compliance effect.