
To set up an OpenSSL server for secure communication, you'll need to create a Certificate Authority (CA) and generate a private key and certificate. This can be done using the OpenSSL command-line tool.
The first step is to create a private key using the RSA algorithm with a key size of 2048 bits. This is done using the command `openssl genrsa 2048`.
You'll also need to create a certificate signing request (CSR) using the private key. This is done using the command `openssl req -new -key private_key.pem -out csr.pem`.
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Setting Up
To set up your OpenSSL server, you'll first need to create a keypair using the P-256 elliptic curve algorithm. This will generate a public and private key.
You can use OpenSSL's command-line interface to create the keypair, and it will be stored in files named after the keypair, such as "server-public-key.pem" and "server-private-key.pem".
The server's private key and certificate must be imported into your SSL_CTX in your C++ code. Unfortunately, OpenSSL wants everything as paths to disk files, which isn't the most secure approach, but it's suitable for our purposes.
To create a certificate, you'll need to specify the server's public key, the domain name, and the expiration date. The certificate will be signed by a certificate authority, such as DigiCert, GlobalSign, or GeoTrust, which must be trusted by your clients.
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Understanding OpenSSL
OpenSSL is a versatile tool for creating and managing secure connections. It's used by many popular services, including web servers and email clients.
OpenSSL is built on top of the SSL/TLS protocol, which stands for Secure Sockets Layer/Transport Layer Security. This protocol ensures that data is encrypted and protected from interception or tampering.
OpenSSL provides a wide range of features, including key generation, certificate management, and encryption.
Root CA
To set up a Root CA, you'll need to generate a private key and certificate. The private key is generated using the command `openssl ecparam -name prime256v1 -genkey -noout -out ca.key`.
The Root CA certificate is generated using the command `openssl req -new -x509 -sha256 -key ca.key -out ca.crt`. You'll be prompted to enter information about the CA, including the country, state, locality, organization, and email address.
The certificate will be generated in the `ca.crt` file. You'll need to enter the following information:
- Country Name (2 letter code)
- State or Province Name (full name)
- Locality Name (eg, city)
- Organization Name (eg, company)
- Organizational Unit Name (eg, section)
- Common Name (e.g. server FQDN or your name)
- Email Address
Once you've entered the information, you'll need to install the certificate on the server and on all client machines to validate the legitimacy of issued certificates.
Certificate
Certificates are a crucial part of the OpenSSL process, and understanding how they work is essential for secure communication.
To generate a Root Certificate Authority (CA), you'll need to create a private key and a certificate. You can do this using the following command line: openssl ecparam -name prime256v1 -genkey -noout -out ca.key. This will create a 256-bit private key in the ca.key file.
The Root CA certificate is then generated using the following command line: openssl req -new -x509 -sha256 -key ca.key -out ca.crt. You'll be prompted to enter information about the CA, including its country, state, locality, organization, and common name.
It's essential to note that the certificate must be installed on the server and all clients to validate the legitimacy of issued certificates. Installing the certificate on the server and clients is a critical step in the process.
To process a Certificate Signing Request (CSR) on the Root CA, you'll need to generate a certificate using the following command line: openssl x509 -req -in server.csr -CA ca.crt -CAkey ca.key -CAcreateserial -out server.crt -days 1000 -sha256. This will generate a certificate in the server.crt file, which must be deployed to the server where the CSR was generated.
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Here's a summary of the steps to generate a certificate:
- Generate the Root CA private key using openssl ecparam -name prime256v1 -genkey -noout -out ca.key
- Generate the Root CA certificate using openssl req -new -x509 -sha256 -key ca.key -out ca.crt
- Process the CSR using openssl x509 -req -in server.csr -CA ca.crt -CAkey ca.key -CAcreateserial -out server.crt -days 1000 -sha256
To generate a server certificate, you'll need to create a private key and a Certificate Signing Request (CSR). You can do this using the following command lines: openssl ecparam -name prime256v1 -genkey -noout -out server.key and openssl req -new -sha256 -key server.key -out server.csr.
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OpenSSL 1.0.2 Limitations
If you're using a version of OpenSSL prior to 1.1.0, you'll have to use SSLv23_method() instead of TLS_method().
OpenSSL 1.0.2 won't automatically initialize itself the first time you use one of its facilities, so you'll need to make sure to set things up properly.
To get English error messages in OpenSSL 1.0.2, you'll need to "load the error strings" as part of your setup.
You'll need to add specific lines at the top of your main() function to make this work.
OpenSSL 1.0.2 is missing a lot of macros for manipulating BIO_METHODs, which can make it tricky to use certain functions.
A "polyfill" header, such as "openssl_backport.h", can help fill in these gaps and make your code more functional.
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Select Signature Algorithms for Handshake
Selecting the right signature algorithms for a handshake is crucial for a smooth TLS connection. In some cases, the wrong algorithms can even cause errors.
For instance, if you're using a smartcard as a certificate provider in Firefox, you might encounter an error while connecting to a server with TLS v1.2 using the httpd mod_ssl module compiled against OpenSSL v1.1.1. However, this error is not present when using OpenSSL v1.1.0.
Spawning a server with the correct command can help display and compare the algorithms negotiated with Firefox in TLS v1.2. This command can be used for both versions of OpenSSL.
To get rid of the error, you can specify the list of authorized algorithms for OpenSSL. In some configurations, the RSA-PSS+SHA256, RSA-PSS+SHA384, and RSA-PSS+SHA512 signature algorithms can cause trouble. Removing them from the list can resolve the issue.
Here are the specific signature algorithms that can cause trouble in some configurations:
- RSA-PSS+SHA256
- RSA-PSS+SHA384
- RSA-PSS+SHA512
Configuring Options
Configuring Options is crucial when setting up your OpenSSL server. The -verify_return_error option is particularly useful, as it allows the command to proceed even if verification errors occur.
This option is especially important when the server requests a client certificate, as it will display verification errors for debugging purposes. By default, the server will proceed with the connection.
The cipher suite used can also impact the effectiveness of the -verify_return_error option, as it may not be able to request a client certificate. In such cases, the option has no effect.
Process a CSR on the Root CA
To process a Certificate Signing Request (CSR) on the Root Certificate Authority (CA), you'll need to generate a certificate using the OpenSSL command line.
The command to generate the certificate is: openssl x509 -req -in server.csr -CA ca.crt -CAkey ca.key -CAcreateserial -out server.crt -days 1000 -sha256.
You should run this command on the server where the CSR was generated, and the resulting certificate will be saved in the server.crt file.
The certificate will be valid for 1000 days, as specified by the -days 1000 option in the command.
After generating the certificate, you must deploy it to the server where you generated the CSR.
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Options

The options for configuring the command are quite extensive. In addition to the common and server only options, this command also supports the options documented in SSL_CONF_cmd(3).
You can specify additional options to customize the behavior of the command. If the cipher suite cannot request a client certificate, for example an anonymous cipher suite or PSK, this option has no effect.
By default, the command validates client certificates and their chains with respect to the (D)TLS Client ("sslclient") purpose. This is done according to the details outlined in openssl-verification-options(1).
If the server requests a client certificate, the command will proceed even if there are verification errors, but these errors will be displayed for debugging purposes. Unless the -verify_return_error option is used, the command will not stop due to verification errors.
Raw public keys can be extracted from the configured certificate/private key.
SSL Filter BIO per Client Connection
To create a secure connection, you need to create an SSL filter BIO for each client connection. This is done by slapping an SSL filter BIO in front of your socket BIO.
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The BIO API in OpenSSL makes this a straightforward process. You can achieve this by using the BIO_new_ssl function, which takes an integer argument to specify whether you want to act like a server or a client.
The integer 0 argument means "act like a server", while 1 means "act like a client." Be careful not to confuse these values, as it can result in your code hanging or erroring out.
Here's a quick rundown of the BIO_new_ssl function:
Remember, if you're unsure, it's always better to err on the side of caution and double-check your values.
SSL Handshake
The SSL handshake is a critical process that establishes a secure connection between a client and a server. You can quickly test and troubleshoot SSL handshake issues using the openssl s_server tool.
To launch an openssl server on port 443 that logs error information, use the following command: openssl s_server -key key -cert cert -accept 443 -CAfile CAfile -state -www. This command will display SSL session states in the console during the server runtime and return connection information to the client through an HTML page.
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The main benefit of testing with openssl s_server is the www option, which enables the browser to display both handshake and transaction details. Opening https://localhost:443 on a browser shows the SSL transaction details in the browser window.
To troubleshoot SSL handshake issues, you can use the -state option to display SSL session states in the console during the server runtime. This can help identify problems with the handshake process.
Here are the options that were passed to the command: OptionDescriptionkeythe private key to usecertthe certificate to useacceptthe server listening portCAfilethe certification authority used to validate client certificatesstatedisplays SSL session states in the console during the server runtimewwwreturns connection informations to the client through an HTML page
By using the openssl s_server tool and the www option, you can quickly test and troubleshoot SSL handshake issues, making it easier to identify and resolve problems with your SSL connection.
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OpenSSL Client from Scratch, Part 3
To create an OpenSSL client from scratch, you'll need to define the SSL/TLS protocol version you want to use, which is typically TLS 1.2 in modern systems.
The OpenSSL library provides a set of functions to handle SSL/TLS protocol versions, including SSL_set_version() and SSL_get_version().
You can use the SSL_set_version() function to set the SSL/TLS protocol version to TLS 1.2.
To verify the selected protocol version, use the SSL_get_version() function, which returns a string indicating the actual protocol version in use.
In our example, we'll use the SSL_set_version() function to set the protocol version to TLS 1.2.
The SSL_get_version() function will then return "TLSv1.2" to indicate the actual protocol version in use.
By setting the protocol version to TLS 1.2, you ensure that your OpenSSL client can communicate securely with servers that support this version.
The OpenSSL library provides a set of functions to handle SSL/TLS protocol versions, including SSL_set_version() and SSL_get_version().
These functions allow you to set and verify the protocol version in your OpenSSL client.
Remember to use the correct protocol version to ensure secure communication with your OpenSSL server.
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Notes
The Notes section is where you'll find some useful tidbits to keep in mind when working with your openssl server.
To debug SSL clients, you can use this command to accept connections from a web browser.
Some SSL clients interpret an empty list of CAs as meaning any CA is acceptable, which is useful for debugging purposes, even if it's a protocol violation.
You can print out the session parameters using the openssl-sess_id command.
Commands and Tools
The openssl server has a range of commands that can be used to perform special operations.
You can end the current SSL connection with a client but still accept new connections by typing 'q' at the start of a line.
Certain commands are recognized and can be used to renegotiate the SSL session, such as 'r' and 'R'.
These commands are only available for TLSv1.2 and below.
The 'P' command sends some plain text down the underlying TCP connection, which should cause the client to disconnect due to a protocol violation.
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Here are some of the special commands that can be used with the openssl server:
You can also use the 'SP' command to print out some session cache status information.
The SSL Library
The SSL Library is a crucial component of any secure online transaction. It's the backbone of HTTPS connections, enabling secure data transfer between servers and clients.
OpenSSL is the most widely used SSL/TLS library, with many tools and modules relying on it. The ngx_http_ssl_module for Nginx and apache mod_ssl module for httpd are two examples of this.
The OpenSSL library comes with a range of useful tools, including the s_client command, which acts as a command-line HTTPS client for analyzing SSL server responses.
SSL_CTX versus SSL
SSL_CTX versus SSL is a fundamental concept in the SSL library. Each TLS connection needs to keep track of some connection-specific state.
TLS is a stateful protocol that requires storing connection-specific state, such as symmetric encryption algorithms and keys, in an object of type struct SSL. OpenSSL stores this state in an object of type struct SSL.
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For our purposes, we don't need to delve into the intricacies of the SSL object. However, it's essential to understand that TLS is a complicated protocol with many human-scale inputs, like encryption algorithms and certificate authorities.
Before creating an SSL connection, you need to create an SSL_CTX context, which factors out shared state across many individual TLS connections. This context is crucial for storing inputs like encryption algorithms and certificate authorities.
You should prohibit insecure and deprecated protocol versions by following the documentation's example, which suggests adding code to restrict these versions.
The SSL Library
The SSL Library is a crucial tool for anyone working with SSL/TLS. It's open source and widely used, with many tools and libraries based on it, including the ngx_http_ssl_module for Nginx and apache mod_ssl module for httpd.
The OpenSSL library comes with many tools for SSL tinkering, making it a must-have for troubleshooting server connections. The openssl s_client command is a command-line HTTPS client that allows analysis of SSL server responses.
OpenSSL also includes the openssl s_server command, which creates an SSL server. This command will be explored in the next section, but it's worth noting that it's a powerful tool for testing and debugging SSL connections.
The OpenSSL library is used by many popular web servers, including Apache httpd, which is the focus of the examples in this article.
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