verify_certificate_identity in the OpenSSL extension in Ruby before 2.0.0 patchlevel 645, 2.1.x before 2.1.6, and 2.2.x before 2.2.2 does not properly validate hostnames, which allows remote attackers to spoof servers via vectors related to (1) multiple wildcards, (1) wildcards in IDNA names, (3) case sensitivity, and (4) non-ASCII characters.

Ruby through 2.4.7, 2.5.x through 2.5.6, and 2.6.x through 2.6.4 allows HTTP Response Splitting. If a program using WEBrick inserts untrusted input into the response header, an attacker can exploit it to insert a newline character to split a header, and inject malicious content to deceive clients. NOTE: this issue exists because of an incomplete fix for CVE-2017-17742, which addressed the CRLF vector, but did not address an isolated CR or an isolated LF.

Ruby through 2.4.7, 2.5.x through 2.5.6, and 2.6.x through 2.6.4 mishandles path checking within File.fnmatch functions.

The OpenSSL extension of Ruby (Git trunk) versions after 2011-09-01 up to 2011-11-03 always generated an exponent value of '1' to be used for private RSA key generation. A remote attacker could use this flaw to bypass or corrupt integrity of services, depending on strong private RSA keys generation mechanism.

Various methods in WEBrick::HTTPRequest in Ruby 1.9.2 and 1.8.7 and earlier do not validate the X-Forwarded-For, X-Forwarded-Host and X-Forwarded-Server headers in requests, which might allow remote attackers to inject arbitrary text into log files or bypass intended address parsing via a crafted header.

Distributed Ruby (aka DRuby) 1.8 mishandles the sending of syscalls.

Distributed Ruby (aka DRuby) 1.8 mishandles instance_eval.

ruby193 uses an insecure LD_LIBRARY_PATH setting.

The ruby_parser-legacy (aka legacy) gem 1.0.0 for Ruby allows local privilege escalation because of world-writable files. For example, if the brakeman gem (which has a legacy dependency) 4.5.0 through 4.7.0 is used, a local user can insert malicious code into the ruby_parser-legacy-1.0.0/lib/ruby_parser/legacy/ruby_parser.rb file.

In Rubyzip before 1.3.0, a crafted ZIP file can bypass application checks on ZIP entry sizes because data about the uncompressed size can be spoofed. This allows attackers to cause a denial of service (disk consumption).