An issue was discovered in Ruby through 2.5.8, 2.6.x through 2.6.6, and 2.7.x through 2.7.1. WEBrick, a simple HTTP server bundled with Ruby, had not checked the transfer-encoding header value rigorously. An attacker may potentially exploit this issue to bypass a reverse proxy (which also has a poor header check), which may lead to an HTTP Request Smuggling attack.
In Puma (RubyGem) before 4.3.2 and before 3.12.3, if an application using Puma allows untrusted input in a response header, an attacker can use newline characters (i.e. `CR`, `LF` or`/r`, `/n`) to end the header and inject malicious content, such as additional headers or an entirely new response body. This vulnerability is known as HTTP Response Splitting. While not an attack in itself, response splitting is a vector for several other attacks, such as cross-site scripting (XSS). This is related to CVE-2019-16254, which fixed this vulnerability for the WEBrick Ruby web server. This has been fixed in versions 4.3.2 and 3.12.3 by checking all headers for line endings and rejecting headers with those 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.
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.
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, the Dir.open, Dir.new, Dir.entries and Dir.empty? methods do not check NULL characters. When using the corresponding method, unintentional directory traversal may be performed.
The Basic authentication code in WEBrick library in Ruby before 2.2.8, 2.3.x before 2.3.5, and 2.4.x through 2.4.1 allows remote attackers to inject terminal emulator escape sequences into its log and possibly execute arbitrary commands via a crafted user name.
The URI.decode_www_form_component method in Ruby before 1.9.2-p330 allows remote attackers to cause a denial of service (catastrophic regular expression backtracking, resource consumption, or application crash) via a crafted string.
Ruby through 2.2.7, 2.3.x through 2.3.4, and 2.4.x through 2.4.1 can expose arbitrary memory during a JSON.generate call. The issues lies in using strdup in ext/json/ext/generator/generator.c, which will stop after encountering a '\0' byte, returning a pointer to a string of length zero, which is not the length stored in space_len.
Net::SMTP in Ruby before 2.4.0 is vulnerable to SMTP command injection via CRLF sequences in a RCPT TO or MAIL FROM command, as demonstrated by CRLF sequences immediately before and after a DATA substring.