diff --git a/src/openssl.cr b/src/openssl.cr
index 4185518d3982..986cd5d29fc9 100644
--- a/src/openssl.cr
+++ b/src/openssl.cr
@@ -1,69 +1,99 @@
 require "./openssl/lib_ssl"
 require "./openssl/error"
 
-# NOTE: To use `OpenSSL`, you must explicitly import it with `require "openssl"`
+# The OpenSSL module allows for access to Secure Sockets Layer (SSL) and Transport Layer Security (TLS)
+# encryption, as well as classes for encrypting data, decrypting data, and computing hashes. It uses
+# the SSL library provided by the operating system, which may be either [OpenSSL](https://openssl.org)
+# or [LibreSSL](https://www.libressl.org).
 #
-# ## OpenSSL Integration
+# WARNING: This module should not be used without first reading the [Security considerations](#security-considerations).
 #
-# - TLS sockets need a context, potentially with keys (required for servers) and configuration.
-# - TLS sockets will wrap the underlying TCP socket, and any further communication must happen through the `OpenSSL::SSL::Socket` only.
+# To create secure sockets, use either `OpenSSL::SSL::Socket::Client` for client applications, or
+# `OpenSSL::SSL::Socket::Server` for servers.  These classes use a default context, but you can provide
+# your own by supplying an `OpenSSL::SSL::Context`.  For more control, consider subclassing `OpenSSL::SSL::Socket`.
 #
-# ## Usage Example
+# Hashing algorithms are provided by classes such as `Digest::SHA256` and `Digest::MD5`.  If you need
+# a different option, you can initialize one using the name of the digest with `OpenSSL::Digest`.
+# A Hash-based Message Authentication Code (HMAC) can be computed using `HMAC` and specifying a digest
+# `Algorithm`.
+#
+# The `OpenSSL::Cipher` class can be used for encrypting and decrypting data.
+#
+# NOTE: To use `OpenSSL`, you must explicitly import it using the `require "openssl"` statement.
+#
+# ## Security Considerations
+#
+# Crystal aims to provide reasonable configuration defaults in accordance with
+# [Mozilla's recommendations](https://wiki.mozilla.org/Security/Server_Side_TLS#Intermediate_compatibility_.28recommended.29).
+# However, these defaults may not be suitable for your application.  It is recommended that you refer
+# to the Open Worldwide Application Security Project (OWASP) cheat sheet on
+# [implementing transport layer protection](https://cheatsheetseries.owasp.org/cheatsheets/Transport_Layer_Security_Cheat_Sheet.html)
+# to ensure the appropriate configuration for your use.
 #
-# Recommended ciphers can be taken from:
-# - [OWASP Wiki](https://www.owasp.org/index.php/Transport_Layer_Protection_Cheat_Sheet#Rule_-_Only_Support_Strong_Cryptographic_Ciphers)
-# - [Cipherli.st](https://cipherli.st/)
-# - A full list is available at the [OpenSSL Docs](https://www.openssl.org/docs/man1.1.0/apps/ciphers.html#CIPHER-STRINGS)
+# If you come across any shortcomings or spots for improvement in Crystal's configuration options,
+# please don't hesitate to let us know by [opening an issue](https://github.com/crystal-lang/crystal/issues/new).
 #
-# Do note that:
-# - Crystal does its best to provide sane configuration defaults (see [Mozilla-Intermediate](https://wiki.mozilla.org/Security/Server_Side_TLS#Intermediate_compatibility_.28default.29)).
-# - Linked version of OpenSSL need to be checked for supporting specific protocols and ciphers.
-# - If any configurations or choices in Crystal regarding SSL settings and security are found to be lacking or need
-#   improvement please [open an issue](https://github.com/crystal-lang/crystal/issues/new) and let us know.
+# ## Usage Example
 #
 # ### Server side
 #
-# NOTE: For the below example to work, a key pair should be attained.
+# An `SSL` server is created with a `TCPServer` and a `SSL::Context`.  You can then use the
+# SSL server like an ordinary TCP server.
+#
+# NOTE: For the below example to work, a certificate and private key should be attained.
 #
 # ```
-# require "socket"
 # require "openssl"
+# require "socket"
 #
-# def server
-#   # Bind new TCPSocket to port 5555
-#   socket = TCPServer.new(5555)
+# PORT = ENV["PORT"] ||= "5555"
 #
-#   context = OpenSSL::SSL::Context::Server.new
-#   context.private_key = "/path/to/private.key"
-#   context.certificate_chain = "/path/to/public.cert"
+# # Bind new TCPServer to PORT
+# socket = TCPServer.new(PORT.to_i)
 #
-#   puts "Server is up"
+# context = OpenSSL::SSL::Context::Server.new
+# context.private_key = "/path/to/private.key"
+# context.certificate_chain = "/path/to/public.cert"
 #
-#   socket.accept do |client|
-#     puts "Got client"
+# puts "Server is up. Listening on port #{PORT}."
 #
-#     bytes = Bytes.new(20)
+# socket.accept do |client|
+#   puts "Got client"
 #
-#     ssl_socket = OpenSSL::SSL::Socket::Server.new(client, context)
-#     ssl_socket.read(bytes)
+#   bytes = Bytes.new(20)
 #
-#     puts String.new(bytes)
+#   OpenSSL::SSL::Socket::Server.open(client, context) do |ssl_socket|
+#     ssl_socket.read(bytes)
 #   end
+#
+#   puts "Client said: #{String.new(bytes)}"
 # end
+#
+# socket.close
+# puts "Server has stopped."
 # ```
 #
 # ### Client side
 #
+# An `SSL` client is created with a `TCPSocket` and a `SSL::Context`. Unlike a SSL server,
+# a client does not require a certificate or private key.
+#
+# NOTE: By default, closing an `SSL::Socket` does not close the underlying socket.  You need to
+#       set `SSL::Socket#sync_close=` to true if you want this behaviour.
+#
 # ```
-# require "socket"
 # require "openssl"
+# require "socket"
 #
-# def client
-#   socket = TCPSocket.new("127.0.0.1", 5555)
+# PORT = ENV["PORT"] ||= "5555"
+#
+# # Bind TCPSocket to PORT and open a connection
+# TCPSocket.open("127.0.0.1", PORT) do |socket|
 #   context = OpenSSL::SSL::Context::Client.new
 #
-#   ssl_socket = OpenSSL::SSL::Socket::Client.new(socket, context)
-#   ssl_socket << "Testing"
+#   OpenSSL::SSL::Socket::Client.open(socket, context) do |ssl_socket|
+#     ssl_socket << "Hello from client!"
+#   end
 # end
 # ```
 module OpenSSL
diff --git a/src/openssl/cipher.cr b/src/openssl/cipher.cr
index bea9a298fc97..c24c821d54dc 100644
--- a/src/openssl/cipher.cr
+++ b/src/openssl/cipher.cr
@@ -3,6 +3,10 @@ require "openssl"
 
 # A class which can be used to encrypt and decrypt data using a specified cipher.
 #
+# NOTE: The ciphers available to an application are determined by the linked version of the system SSL library.
+#       A comprehensive list of ciphers can be found in the
+#       [OpenSSL Cipher documentation](https://www.openssl.org/docs/man3.0/man1/openssl-ciphers.html#CIPHER-STRINGS).
+#
 # ```
 # require "random/secure"
 #
diff --git a/src/openssl/ssl/context.cr b/src/openssl/ssl/context.cr
index a46e924346a7..5db3e754e79b 100644
--- a/src/openssl/ssl/context.cr
+++ b/src/openssl/ssl/context.cr
@@ -294,19 +294,31 @@ abstract class OpenSSL::SSL::Context
     raise OpenSSL::Error.new("SSL_CTX_use_PrivateKey_file") unless ret == 1
   end
 
-  # Specify a list of TLS ciphers to use or discard.
+  # Specify a list of TLS ciphers to use or discard for TLSv1.2 and below.
   #
-  # This affects only TLSv1.2 and below. See `#security_level=` for some
-  # sensible system configuration.
+  # See `#security_level=` for some sensible system configuration.
+  #
+  # This method does not impact TLSv1.3 ciphersuites. Use `#cipher_suites=`
+  # to configure those.
+  #
+  # NOTE: The ciphers available to an application are determined by the
+  #       linked version of the system SSL library. A comprehensive list
+  #       of ciphers can be found in the
+  #       [OpenSSL Cipher documentation](https://www.openssl.org/docs/man3.0/man1/openssl-ciphers.html#CIPHER-STRINGS).
   def ciphers=(ciphers : String)
     ret = LibSSL.ssl_ctx_set_cipher_list(@handle, ciphers)
     raise OpenSSL::Error.new("SSL_CTX_set_cipher_list") if ret == 0
     ciphers
   end
 
-  # Specify a list of TLS cipher suites to use or discard.
+  # Specify a list of TLS ciphersuites to use or discard for TLSv1.3.
   #
   # See `#security_level=` for some sensible system configuration.
+  #
+  # NOTE: The ciphersuites available to an application are determined by the
+  #       linked version of the system SSL library. A comprehensive list
+  #       of ciphersuites can be found in the
+  #       [OpenSSL Cipher documentation](https://www.openssl.org/docs/man3.0/man1/openssl-ciphers.html#TLS-v1.3-cipher-suites).
   def cipher_suites=(cipher_suites : String)
     {% if LibSSL.has_method?(:ssl_ctx_set_ciphersuites) %}
       ret = LibSSL.ssl_ctx_set_ciphersuites(@handle, cipher_suites)