Have you ever discussed how long you plan to take unpaid maternity leave? It sounds like your employer is already expecting you to not to come back based on the fact he has started preparing another employee. This is tricky because you are trying to keep your health coverage active while you are essentially quiting your job, which sort of puts you in a vulnerable position. You should wait to tell your boss you aren't coming back until your agreed upon leave is almost done, and here is why. If you notify them you arent coming back, you are essentially quiting and they can terminate you at any point forward and then you are no longer elligible for your company's health benefit. Plus, since you chose to quit, you may not qualify for COBRA (? I don't know, heck on this) since you weren't fired. So now you are right before your delivey and you need insurance, but most insurance companies wont begin new coverage until post delivery with you as late in the pregnancy as you are, so I would try to not lose your company's health coverage by basically quitting in advance of your maternity leave. It sounds like you need to start researching a new health coverage plan regardless and it would be smart to have something in the works incase your boss terminates you before you anticipate. Also, check into your state's laws about maternity leave, many states don't protect your right to your job after 12 weeks, even if your employer agrees to a longer time frame (so get whatever maternity leave you agree on in writing- it is the only way to protect yourself and prove the agreement!). If you have a mediaclly complicated (and expensive) delivery and your baby ends up in the NICU, your employer may try to retroactively date your end of employment date to before the delivery since you stated you werent coming back and your claims would be denied coverage by their insurance carrier as you were not techinically part of the company during the time those medical services were rendered.