Every month, Fidelity Investments contributes exactly $167 apiece toward the student-loan payments of almost 9,000 of its employees. In most cases, Fidelity can make a simple electronic transfer to student-loan servicers, the patchwork of companies that handle billing and other administrative functions for student loans in the United States, of which there are over $1.5 trillion outstanding. A few servicers, though, force Fidelity to issue paper checks for individual loan payments—and if there’s an error, the check eventually gets sent back.