sherware on "[Plugin: Jetpack by WordPress.com] Error 500 Connecting Jetpack"

Here's the log entries from the server 500 error.

2016-01-25 13:06:58 10.138.41.219 GET /wp-content/plugins/jetpack/_inc/fonts/jetpack/jetpack.woff - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 404 3 50 37
2016-01-25 13:07:46 10.138.41.219 POST /wp-cron.php doing_wp_cron=1453727262.5924570560455322265625 80 - 184.73.254.165 WordPress/4.4.1;+http://philsherwood.com 500 0 64 4142
2016-01-25 13:07:46 10.138.41.219 GET /wp-admin/admin.php page=jetpack 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 200 0 0 5309
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/_inc/genericons/genericons/genericons.css ver=3.1 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 200 0 0 247
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/_inc/jp.js ver=3.9.1-20121111 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 200 0 0 140
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/css/jetpack-admin.min.css ver=3.9.1-20121016 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 200 0 0 519
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/_inc/fonts/jetpack/jetpack.woff - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 404 3 50 34
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/images/the-cloud-sm.svg - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 404 3 50 63
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/images/connect-plug.svg - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 404 3 50 35
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/_inc/fonts/automatticons/automatticons.woff - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 404 3 50 45
2016-01-25 13:07:48 10.138.41.219 GET /wp-content/plugins/jetpack/images/jetpack-logo.svg - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 404 3 50 89
2016-01-25 13:07:49 10.138.41.219 GET /wp-content/plugins/jetpack/_inc/fonts/automatticons/automatticons.ttf - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 200 0 0 271
2016-01-25 13:08:00 10.138.41.219 POST /wp-admin/admin-ajax.php - 80 - 104.138.206.171 Mozilla/5.0+(Windows+NT+10.0;+WOW64)+AppleWebKit/537.36+(KHTML,+like+Gecko)+Chrome/47.0.2526.111+Safari/537.36 200 0 0 1601