Background: Retrospective studies have found that people with elevated social anxiety (SA) show a preference for digital/online communication, which may be due to perceptions of enhanced emotional safety. Whether these preferences for/benefits of digital compared to face-to-face communication manifest in the real world has yet to be explored. Methods: We recruited samples of college students (N = 125) and community adults (N = 303) with varying levels of SA, sampled their emotions during digital and face-to-face communication using ecological momentary assessment (EMA) (Study 1) and a day reconstruction method (DRM) (Study 2), and preregistered our hypotheses ( https://osf.io/e4y7x/ ). Results: Results from both studies showed that SA did not predict the likelihood of engaging in digital compared to face-to-face communication, and SA was associated with less positive and more negative emotions regardless of communication medium. Study 2 also showed that whether digital communication was synchronous (e.g., in real time via phone/video chat) or asynchronous (e.g., texting/instant messaging) did not impact the association between SA and emotions. Limitations: EMA and DRM methods, despite their many advantages, may be suboptimal for assessing the occurrence of digital communication behaviors relative to more objective methods (e.g., passively collecting smartphone communication data). Using event-contingent responding may have also yielded more reports of digital communication, thus strengthening our power to detect small, cross-level interaction effects. Conclusions: These results challenge beliefs that digital/online communication provides a source of emotional safety for people with elevated SA and suggests a greater need to address SA-related emotional impairments across digital communication platforms.