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A core problem in the development and maintenance of crowd-sourced filter lists is that their maintainers cannot confidently predict whether (and where) a new filter list rule will break websites. This is a result of enormity of the Web, which prevents filter list authors from broadly understanding the impact of a new blocking rule before they ship it to millions of users. The inability of filter list authors to evaluate the Web compatibility impact of a new rule before shipping it severely reduces the benefits of filter-list-based content blocking: filter lists are both overly-conservative (i.e. rules are tailored narrowly to reduce the risk of breaking things) and error-prone (i.e. blocking tools still break large numbers of sites). To scale to the size and scope of the Web, filter list authors need an automated system to detect when a new filter rule breaks websites, before that breakage has a chance to make it to end users. In this work, we design and implement the first automated system for predicting when a filter list rule breaks a website. We build a classifier, trained on a dataset generated by a combination of compatibility data from the EasyList project and novel browser instrumentation, and find it is accurate to practical levels (AUC 0.88). Our open source system requires no human interaction when assessing the compatibility risk of a proposed privacy intervention. We also present the 40 page behaviors that most predict breakage in observed websites.