The openssl gem for Ruby uses the same initialization vector (IV) in GCM Mode (aes-*-gcm) when the IV is set before the key, which makes it easier for context-dependent attackers to bypass the encryption protection mechanism.

Directory traversal vulnerability in WEBrick in Ruby 1.8.4 and earlier, 1.8.5 before 1.8.5-p231, 1.8.6 before 1.8.6-p230, 1.8.7 before 1.8.7-p22, and 1.9.0 before 1.9.0-2, when using NTFS or FAT filesystems, allows remote attackers to read arbitrary CGI files via a trailing (1) + (plus), (2) %2b (encoded plus), (3) . (dot), (4) %2e (encoded dot), or (5) %20 (encoded space) character in the URI, possibly related to the WEBrick::HTTPServlet::FileHandler and WEBrick::HTTPServer.new functionality and the :DocumentRoot option.

Directory traversal vulnerability in WEBrick in Ruby 1.8 before 1.8.5-p115 and 1.8.6-p114, and 1.9 through 1.9.0-1, when running on systems that support backslash (\) path separators or case-insensitive file names, allows remote attackers to access arbitrary files via (1) "..%5c" (encoded backslash) sequences or (2) filenames that match patterns in the :NondisclosureName option.

An issue was discovered in Ruby through 2.6.7, 2.7.x through 2.7.3, and 3.x through 3.0.1. A malicious FTP server can use the PASV response to trick Net::FTP into connecting back to a given IP address and port. This potentially makes curl extract information about services that are otherwise private and not disclosed (e.g., the attacker can conduct port scans and service banner extractions).

An issue was discovered in Ruby 2.5.x through 2.5.7, 2.6.x through 2.6.5, and 2.7.0. If a victim calls BasicSocket#read_nonblock(requested_size, buffer, exception: false), the method resizes the buffer to fit the requested size, but no data is copied. Thus, the buffer string provides the previous value of the heap. This may expose possibly sensitive data from the interpreter.

Off-by-one error in the encodes function in pack.c in Ruby 1.9.3 and earlier, and 2.x through 2.1.2, when using certain format string specifiers, allows context-dependent attackers to cause a denial of service (segmentation fault) via vectors that trigger a stack-based buffer overflow.

Directory traversal vulnerability in controller/concerns/render_redirect.rb in the Wicked gem before 1.0.1 for Ruby allows remote attackers to read arbitrary files via a %2E%2E%2F (encoded dot dot slash) in the step.

Ruby before 1.8.6-p114 does not reset the random seed upon forking, which makes it easier for context-dependent attackers to predict the values of random numbers by leveraging knowledge of the number sequence obtained in a different child process, a related issue to CVE-2003-0900.

In Ruby before 2.2.10, 2.3.x before 2.3.7, 2.4.x before 2.4.4, 2.5.x before 2.5.1, and 2.6.0-preview1, an attacker controlling the unpacking format (similar to format string vulnerabilities) can trigger a buffer under-read in the String#unpack method, resulting in a massive and controlled information disclosure.

The SecureRandom.random_bytes function in lib/securerandom.rb in Ruby before 1.8.7-p352 and 1.9.x before 1.9.2-p290 relies on PID values for initialization, which makes it easier for context-dependent attackers to predict the result string by leveraging knowledge of random strings obtained in an earlier process with the same PID.