Quick Question: Does having a master's degree affect (negatively or positively) your chances of getting a scholarship for a second master's?

Quick Answer: It depends. If you are applying for a 2nd masters and it’s close in content to your original one (for example, if you have a masters in a business topic & are applying for an MBA or another business-related masters) it can be harder to get in & definitely harder to get a scholarship because it’s tougher to convince the adcom that you really need this additional degree. It’s critical to make a strong argument for why this 2nd masters is critical to your success in your career goals.

Some programs (MBAs in particular) are also wary of “career students” and an existing masters can again hurt your chances for that reason. (They value work experience more than multiple masters). Ultimately though, your chance at a scholarship depends less on whether or not you have an existing masters and more on how competitive you are for that school. If you are a much stronger applicant than average then you will have a stronger shot at a scholarship.