Yes, you can apply with multiple health insurance companies at the same time, but the time and effort involved in doing so may not be productive. Most insurance companies will request that you submit the first month premium along with your application. This shows good faith that they are not wasting your time in processing your application. If you are approved for coverage, you have the right to change your mind and get a refund on your initial deposit amount. Some insurance companies may deduct an application processing fee from your deposit if you choose to not accept their coverage. Although the underwriting guidelines may differ from one insurance company to another, your ability to qualify for coverage will be the same with the different companies in about 80% of the cases. Are you considering submitting multiple applications because you are concerned about a pre-eisting medical condition or your health history? If so, there may be a more convenient and efficient way for you to accomplish this. Also, in which state do you reside?