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Your supervisor knows you need insurance, so I doubt your resignation will surprise her. You really don't have a choice in this matter; you aren't leaving to get paid a dollar more per hour somewhere else. As others have said, don't resign until you have a solid offer, then speak to her before handing in a formal resignation letter.
Hey, you have to make a living and you need health insurance (by law), so if your current company doesn't offer it, c'est la vie. It's business, you and your supervisor have business relationships not friendships requiring loyalty, get a better offer and move on to a better life for you and your family.
It sounds like she's aware of the benefits issue, so in that sense, she already has a heads up. Do not say anything else until you have a written job offer for a new position. At that point, you can let her know. I'd speak to her on the phone, let her know your letter of resignation will be forthcoming and then you can also say that she's been a good boss to work for, etc. But in the letter itself, just make it a very basic statement that you will be leaving effective as of xx/xx/xxxx.
Like was mentioned don't say anything until you are certain you have another job. I was let go a few days after giving my 2 week notice because I was privy to sensitive information where I worked. In your letter of resignation explain you are leaving because you need health benefits. Perhaps the company will come to the realization that they are losing good people for failing to provide benefits.
Quitting is rarely a ethical dilemma. Only if you promised to stay until a certain date and the employer promised to keep you would it be objectionable to quit.
Otherwise a polite call will suffice telling your boss that you appreciate the awesome work relationship but a great opportunity came along so you will move on.
I don't understand why people keep posting these kinds of questions. What part of "I quit" is so hard? Your manager would let you go in a New York minute if told to do so.
And yes, wait until your next job is in the bag. Don't jump the gun.
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