Yes, you can lose money in a Roth IRA. However, these losses can be mitigated with patience and control. Your investments will fluctuate along with the market, so if the market nosedives, then so can your investments. However, market fluctuations balance out over time. Patience is the key. The surest way to take a direct hit on your Roth IRA is by making an early withdrawal. If you take money out of your Roth IRA too early, you will get taxed on that income, plus another tax penalty of 10 percent. The longer you can leave your investment untouched, the less likely you are to lose money.