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Why, when, and how do activist groups engage across ideological and tactical boundaries? This paper examines the boundary-spanning behaviors of moderates and radicals within social movements, analyzing how activist groups endorse each other despite their differences and the potential negative repercussions of such endorsements. Theories emphasizing instrumental purposes and emergent identities explain why collaborations and coalitions form, but they offer less insight into the timing and asymmetry of inter-factional dynamics. This paper argues that moderates and radicals adapt strategically to an unfolding political process. Short-term events such as interactions with various institutional actors, brief windows of political opportunity, elite endorsements, and international support alter political access and audience scope, affecting how movement actors prioritize their worthiness, unity, numbers, and commitment before the audiences. Such shifting priorities, in turn, shapes inter-faction relations. This analysis leverages original inter-organizational endorsements network and political event datasets extracted from over 730,000 Telegram posts during the 2019 Hong Kong Anti-Extradition Amendment Bill protests. Blockmodels and relational event models results show that moderates and radicals are more likely to endorse across factional lines when interactions with institutional actors signal restricted access to the polity and expose movement actors to external audiences. The findings contribute to broad discussions on boundary-spanning behaviors, inter-organizational coordination, movement dynamics, and contentious strategies.