From 35338fc220b34cd9aed4bc7b78c24b1b5a58e6df Mon Sep 17 00:00:00 2001
From: Flavio Heleno <flaviohbatista@gmail.com>
Date: Tue, 29 Dec 2020 20:13:06 -0300
Subject: [PATCH] (*) Added instructions for generating ssl files on macOS

---
 README.md    |  6 ++++--
 ssl-macOS.md | 58 ++++++++++++++++++++++++++++++++++++++++++++++++++++
 2 files changed, 62 insertions(+), 2 deletions(-)
 create mode 100644 ssl-macOS.md

diff --git a/README.md b/README.md
index d5620f4..43bb988 100644
--- a/README.md
+++ b/README.md
@@ -31,11 +31,13 @@ $ ./vendor/bin/http_test_server > /dev/null 2>&1 &
 Then generate ssh certificates:
 
 ```bash
-$ cd ./tests/server/ssl 
+$ cd ./tests/server/ssl
 $ ./generate.sh
-$ cd ../../../ 
+$ cd ../../../
 ```
 
+Note: If you are running this on macOS and get the following error: "Error opening CA Private Key privkey.pem", check [this](ssl-macOS.md) file.
+
 Now run the test suite:
 
 ``` bash
diff --git a/ssl-macOS.md b/ssl-macOS.md
new file mode 100644
index 0000000..c37468d
--- /dev/null
+++ b/ssl-macOS.md
@@ -0,0 +1,58 @@
+# Generating SSL Certificates on macOS
+
+When generating SSL Certificates on macOS, you must ensure that you're using brew's openssl binary and not the one provided by the OS.
+
+To do that, find out where your openssl is installed by running:
+
+```bash
+$ brew info openssl
+```
+
+You should see something like this:
+
+```
+openssl@1.1: stable 1.1.1i (bottled) [keg-only]
+Cryptography and SSL/TLS Toolkit
+https://openssl.org/
+/usr/local/Cellar/openssl@1.1/1.1.1i (8,067 files, 18.5MB)
+  Poured from bottle on 2020-12-11 at 11:31:46
+From: https://github.com/Homebrew/homebrew-core/blob/HEAD/Formula/openssl@1.1.rb
+License: OpenSSL
+==> Caveats
+A CA file has been bootstrapped using certificates from the system
+keychain. To add additional certificates, place .pem files in
+  /usr/local/etc/openssl@1.1/certs
+
+and run
+  /usr/local/opt/openssl@1.1/bin/c_rehash
+
+openssl@1.1 is keg-only, which means it was not symlinked into /usr/local,
+because macOS provides LibreSSL.
+
+If you need to have openssl@1.1 first in your PATH run:
+  echo 'export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"' >> /Users/flavio/.bash_profile
+
+For compilers to find openssl@1.1 you may need to set:
+  export LDFLAGS="-L/usr/local/opt/openssl@1.1/lib"
+  export CPPFLAGS="-I/usr/local/opt/openssl@1.1/include"
+
+For pkg-config to find openssl@1.1 you may need to set:
+  export PKG_CONFIG_PATH="/usr/local/opt/openssl@1.1/lib/pkgconfig"
+
+==> Analytics
+install: 855,315 (30 days), 2,356,331 (90 days), 7,826,269 (365 days)
+install-on-request: 139,236 (30 days), 373,801 (90 days), 1,120,685 (365 days)
+build-error: 0 (30 days)
+```
+
+The important part is this:
+
+> echo 'export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"' >> /Users/flavio/.bash_profile
+
+Instead of running `./tests/server/ssl/generate.sh`, you should instead run:
+
+```bash
+$ PATH="/usr/local/opt/openssl@1.1/bin ./tests/server/ssl/generate.sh
+```
+
+You should now be good to go.