SSH Woes with Vagrant, Windows, and AWS

Dumping this here in case anyone has a similar problem.

I was trying to use Vagrant to spin up dev boxes on aws. Every time I got to the rysnc part of my day, I got the error “Warning: Unprotected Private Key File, this private key will be ignored.”

I googled a bunch and got a lot of really unhelpful answers, mostly dealing with UNIX-like environments. I also tried messing with the Windows file permissions. Fail all around. Here’s how I finally solved it:

Step 1: Install Cygwin Terminal. Find private key and look at it

$ ls -la
drwxrwx---+ 1 kellb_000      None      0 Jun 25 12:51 .
drwxrwx---+ 1 Administrators SYSTEM    0 Jun 25 13:11 ..
-rw-rw----+ 1 kellb_000      None   1696 Jun 25 12:50 Vagrant.pem

Step 2: Chmod file to something more restrictive.

$ chmod 400 Vagrant.pem
$ ls -la
drwxrwx---+ 1 kellb_000      None      0 Jun 25 12:51 .
drwxrwx---+ 1 Administrators SYSTEM    0 Jun 25 13:11 ..
-r--r-----+ 1 kellb_000      None   1696 Jun 25 12:50 Vagrant.pem

Gee that’s odd, that gave it 440, not the 400 I asked for. Oh, hm, it doesn’t have a group. That’s odd. Let’s give it one and try again.

$ chgrp SYSTEM Vagrant.pem
$ chmod 400 Vagrant.pem
drwxrwx---+ 1 kellb_000      None      0 Jun 25 12:51 .
drwxrwx---+ 1 Administrators SYSTEM    0 Jun 25 13:11 ..
-r--------+ 1 kellb_000      SYSTEM 1696 Jun 25 12:50 Vagrant.pem

Much better. I then tried bringing up the vagrant box, and success! At least, until it failed for entirely unrelated reasons. Hooray.