When working with Ubuntu/Debian systems, you'll notice that development packages typically follow the lib[package-name]-dev naming pattern. For OpenSSL, the correct package name is libssl-dev, not openssl-dev as you might find in some older documentation.

Here's the correct command to install both OpenSSL and its development headers:

sudo apt-get update
sudo apt-get install openssl libssl-dev

When compiling Nginx from source, the libssl-dev package provides:

• Header files needed for SSL/TLS functionality
• Static libraries for linking
• Development tools required during compilation

After installation, you can verify the headers are in place:

ls -l /usr/include/openssl/

You should see files like ssl.h, err.h, and other OpenSSL headers.

When compiling Nginx, you'll typically include SSL support like this:

./configure --with-http_ssl_module \
            --with-openssl=/usr/include/openssl
make
sudo make install

Some developers encounter these issues:

• Using outdated package names (openssl-dev instead of libssl-dev)
• Forgetting to update package lists before installation
• Missing dependencies when compiling (install build-essential first)

When compiling Nginx from source on Ubuntu, many developers encounter confusion regarding the OpenSSL development packages. The book reference mentions openssl-dev, but Ubuntu's package manager doesn't recognize this exact name.

In Ubuntu/Debian systems, development packages typically follow the lib[package-name]-dev naming pattern. For OpenSSL, the correct package is:

sudo apt-get install libssl-dev openssl

After installation, verify the headers are properly installed:

ls /usr/include/openssl/
# Should show ssl.h, crypto.h, etc.

When configuring Nginx, ensure it can find the OpenSSL headers:

./configure --with-http_ssl_module \
--with-openssl=/usr/include/openssl \
[other configuration options]

If you encounter SSL-related errors during Nginx compilation:

# Check for missing dependencies
sudo apt-get build-dep nginx

# Verify the OpenSSL version
openssl version

For specific OpenSSL versions, you might need to compile from source:

wget https://www.openssl.org/source/openssl-1.1.1.tar.gz
tar -xzf openssl-1.1.1.tar.gz
cd openssl-1.1.1
./config --prefix=/usr/local/openssl --openssldir=/usr/local/openssl
make
sudo make install

When using custom OpenSSL builds, update your environment variables:

export LD_LIBRARY_PATH=/usr/local/openssl/lib:$LD_LIBRARY_PATH
export PATH=/usr/local/openssl/bin:$PATH