Pseudo-element after not showing? [duplicate]

You don’t seem to be using a pseudo-element at the moment. Try this setting .help-tip to .help-tip::after and giving is content: "" and display: inline-block:

.help-tip::after {
    content: "";
    display: inline-block;
    cursor: pointer;
    width: 10px;
    height: 10px;
    background-repeat: no-repeat;
    background-image: url("/assets/small-help-icon.gif");
}