I have two 1099 B forms from ETrade. One is current account, and the other was a work account used for holding RSU's and ESPPs. Should I be entering the cost basis twice?

Yes, you should enter the cost basis for each 1099-B form separately. These forms are for different accounts and may have different types of transactions. Here's how to handle it:

1. Current Account: For your personal account, report the cost basis and proceeds for each transaction listed on the 1099-B. Ensure that the cost basis matches what is reported on the form, or adjust it if necessary (e.g., for missing or incorrect basis). 
2. Work Account (RSUs and ESPPs): For the account holding RSUs (Restricted Stock Units) and ESPPs (Employee Stock Purchase Plans), you'll also need to report the cost basis for each transaction. Be aware that:

• RSUs: The cost basis is typically the fair market value (FMV) of the shares on the vesting date.
• ESPPs: The cost basis may include the purchase price and any discount provided by your employer. If the shares are sold before meeting the holding period requirements, part of the gain may be treated as ordinary income.