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.

Thank you, Dave. However, both 1099 B's have the same assets listed for my RSUs. 
I had the work account until Sept of last year. This held all of the RSUs and ESPPs.
I then transferred the assets from that account to my personal account. 
The 1099B for my personal account has other gains and losses in addition to the work stocks I transferred. 
The 1099 B from the work account, I only have RSU listed. So, I'm afraid, it will miscalculate the tax bill if have them listed twice. 

Report the 1099 B from your personal account since the assets were transferred over from the work account.  If the IRS asks about this, you can say that all your money from your work account was moved to your personal account. The work 1099 B is a duplicate because all of the information from it is transferred to your work account.