Jeff Shields kitsguru

How to set up stress-free SSL on an OS X development machine

One of the best ways to reduce complexity (read: stress) in web development is to minimize the differences between your development and production environments. After being frustrated by attempts to unify the approach to SSL on my local machine and in production, I searched for a workflow that would make the protocol invisible to me between all environments.

Most workflows make the following compromises:

Use HTTPS in production but HTTP locally. This is annoying because it makes the environments inconsistent, and the protocol choices leak up into the stack. For example, your web application needs to understand the underlying protocol when using the secure flag for cookies. If you don't get this right, your HTTP development server won't be able to read the cookies it writes, or worse, your HTTPS production server could pass sensitive cookies over an insecure connection.
Use production SSL certificates locally. This is annoying

macOS 10.12 Sierra Setup

Custom recipe to get macOS 10.12 Sierra running from scratch, setup applications and developer environment. This is very similar (and currently mostly the same) as my 10.11 El Capitan setup recipe and 10.10 Yosemite setup recipe. I am currently tweaking this for 10.12 Sierra and expect to refine this gist over the next few weeks.

I use this gist to keep track of the important software and steps required to have a functioning system after a semi-annual fresh install. I generally reinstall each computer from scratch every 6 months, and I do not perform upgrades between releases.

This keeps the system performing at top speeds, clean of trojans, spyware, and ensures that I maintain good organizational practices for my content and backups. I highly recommend this.

You are encouraged to fork this and modify it to your heart's content to match your o

	# First, generate the key. You will be prompted to enter a password, but we will strip it out in the next step:
	openssl genrsa -des3 -out server.orig.key 2048


	# Then, stip out the password:
	openssl rsa -in server.orig.key -out server.key


	# Edit the OSX openssl config file to include your alternate names.
	# Edit the 'subjectAltName' field. E.g.:

	# First, generate the key. You will be prompted to enter a password, but we will strip it out in the next step:
	openssl genrsa -des3 -out server.orig.key 2048


	# Then, stip out the password:
	openssl rsa -in server.orig.key -out server.key


	# Edit the OSX openssl config file to include your alternate names.
	# Edit the 'subjectAltName' field. E.g.: