During periods of strict internet censorship, maintaining access to online information and communication becomes paramount. However, users must often navigate complicated pathways to find effective censorship circumvention technologies (CCTs). Utilizing real-time data from over 50M posts collected from Twitter and Telegram from September 18th, 2022, to January 31st, 2023, during a peak period of censorship, we examined the impact of CCTs, such as VPNs, proxies, and alternative connectivity solutions, on digital rights, privacy, and internet governance. Through a mixed-method analysis, our findings reveal user resilience and adaptability when the community collaboratively shares and discusses knowledge and resources. First, we developed a codebook for discussions considering English and, for the first time, Persian posts, highlighting the main problems users encounter when attempting to bypass the internet restrictions. Several concerns were common across these discourses, such as traceability, identifiability, and accidental use of malicious configurations. Our temporal study, conducted over 20 weeks, showed shifts in VPN preferences due to changing censorship strategies, with the inclusion of more privacy-focused and accessibility features leading to higher adoption. We also found several dedicated popular VPN channels that shared malicious files masked as free VPN services.