Website publishers cannot monetize the ad impressions that are prevented by ad-blockers. Publishers can then employ anti-ad-blockers that force users to choose between either accepting ad impressions by whitelisting the website in the ad-blocker, or leaving the website without accessing the content. This study delineates the mechanisms of how willingness to whitelist/leave the website are affected by the request’s sensitivity to recipients as well as the users’ psychological reactance and evaluation of the website advertising. We tested the proposed relationships using an online panel sample of 500 ad-blocker users, who were asked about their willingness to whitelist/leave their favorite online newspaper after receiving a hypothetical anti-ad-blocker request—four alternative requests with different sensitivity levels were created and randomly assigned to the participants. The results confirmed that (a) the request’s sensitivity can improve the recipient’s compliance, (b) users’ psychological reactance plays an important role in explaining the overall phenomenon, and (c) a favorable evaluation of the website advertising can improve willingness to whitelist. These findings help to better understand user response to anti-ad-blockers and may also help publishers increase their whitelist ratios.