Dock not restarting after killall Dock
tl;dr Run: killall 'System Preferences' &gt; /dev/null 2&gt;&amp;1 &amp;&amp; rm '~/Library/Application Support/Dock/desktoppicture.db' &amp;&amp; killall Dock

For anyone who may experience this issue in the future, my issue was with the file located at ~/Library/Application Support/Dock/desktoppicture.db.

After doing some googling, I cam across the following two threads, here and here. Both of which suggest removing the desktoppicture.db with rm '~/Library/Application Support/Dock/desktoppicture.db' &amp;&amp; killall Dock which solved the issue for me. You can read in more detail about the issue and proposed solution on the second of the two linked threads above