These may need to use the "socket" part of the spark plug socket to help with reach.
Meaning that the plug may be too long for the socket to fully reach the nut on the shell of the plug - because the socket may be a spark plug type, but if the terminal is interfereing with the "square" of the 3/8's socket
The problem may not be with the width, more the depth - meaning that when you use a 3/8 - ratchet, the "3/8" used to hold the socket is the problem - the clearance of the terminal - because of the length (Height) of the plug is a potential problem.
The grommet used to hold the plug in the socket, can also add a fitting problem - the grommet can't fit the insulator - the hole for it may be too small for the insulator so it's too tight to fit. So, you can't seem to push into the hole to hold the insulator, so it doesn't break and let the tool seat the socket onto the nut of the shell.
There's some grey area of conditions of you can encounter with plugs and issues around both the boot, the "coil on the plug" and these in seat types of designs - where dirt, debris and age can erode the boot to make it difficult to remove the plug because there is so much dirt and debris in the hole to keep the socket lifted away from the shell so it can't even reach the nut let alone fit the hole.
From a Ford Focus...
So, if you get the whole boot out, what is still in the hole - is there dirt or debris?
So, we need to know what kind of conditions or what you're experiencing?