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To provide secure content delivery, Transport Layer Security (TLS) has become a de facto standard over a couple of decades. However, TLS has a long history of security weaknesses and drawbacks. Thus, the security of TLS has been enhanced by addressing security problems through continuous version upgrades. Meanwhile, to provide fast content delivery globally, websites (or origin web servers) need to deploy and administer many machines in globally distributed environments. They often delegate the management of machines to web hosting services or content delivery networks (CDNs), where the security configurations of distributed servers may vary spatially depending on the managing entities or locations. Based on these spatial differences in TLS security, we find that the security level of TLS connections (and their web services) can be lowered. After collecting the information of (web) domains that exhibit different TLS versions and cryptographic options depending on clients' locations, we show that it is possible to redirect TLS handshake messages to weak TLS servers, which both the origin server and the client may not be aware of. We investigate 7M domains with these spatial differences of security levels in the wild and conduct the analyses to better understand the root causes of this phenomenon. We also measure redirection delays at various locations in the world to see whether there are noticeable delays in redirections.