Offer your thoughts or opinion on the input financial query or topic using your financial background.

When does it make financial sense to take advantage of employer's tuition reimbursement program?
If you have decided to do the degree, and are simply deciding whether to accept employer funding for it or not, take the funding. I see no difference between "my employer doesn't pay my tuition" and "my employer paid my tuition but I had to pay it back because I moved on". Therefore there is no downside to letting them pay the tuition. If you want to move on before the two years (or whatever) is up, you pay back that interest free loan. You are still ahead over self funding the degree. If you have not decided to do the degree, and are letting the employer-funded tuition figure into your decision process, stop that right now. Doing a degree is hard work. You will either work much longer hours than you do now, or live on a lower salary, or more likely both. You might enjoy it, you might be worth more afterwards, and it might open the door to a raft of careers available only to those with the degree. The actual cost of the tuition is unlikely to be significant in this decision process. Removing it (by assuming the employer pays it) should still not be done. If it's worth doing when you self fund, then do it and relax knowing you won't feel trapped at your employer even if you let them pay it (or lend you the money for it if you end up leaving.)