Abstract Middleboxes, such as proxies, firewalls and NATs play an important role in the modern Internet ecosystem. On one hand, they perform advanced functions, e.g. traffic shaping, security or enhancing application performance. On the other hand, they turn the Internet into a hostile ecosystem for innovation, as they limit the deviation from deployed protocols. It is therefore essential, when designing a new protocol, to first understand its interaction with the elements of the path. The emerging area of crowdsourcing solutions can help to shed light on this issue. Such approach allows us to reach large and different sets of users and also different types of devices and networks to perform Internet measurements. In this paper, we show how to make informed protocol design choices by using a crowdsourcing platform. We consider a specific use case, namely the case of pervasive encryption in the modern Internet. Given the latest public disclosures of the NSA global surveillance operations, the issue of privacy in the Internet became of paramount importance. Internet community efforts are thus underway to increase the adoption of encryption. Using a crowdsourcing approach, we perform large-scale TLS measurements to advance our understanding on whether wide adoption of encryption is possible in today's Internet.