How do I insert 1099-B?

Provide wording of the error message

Said I need to update, so I did to Delux and it’s still not letting me? 

Sounds like you are trying to enter a 1099-B in TurboTax Deluxe Desktop:  Try these steps:

Here's where you enter or import your 1099-B in TurboTax:

1. Open or continue your return.
2. Navigate to the 1099-B section:
   • TurboTax Desktop: Search for 1099-B and select the Jump to link.
3. Follow the onscreen instructions. When you reach Let's import your tax info, choose how you want to enter your 1099-B:
   • To import your form, select your brokerage or financial institution from the list. Enter your sign-in credentials for your account, then select Get my form.
   • If you want to enter your 1099-B manually, select Enter a different way, then select your investment type on the next screen.
4. On the following screens, answer the questions about your 1099-B. When you reach the Review your sales screen, the form you just entered should be listed.
5. If you need to add another 1099-B, select Add investments. Otherwise, select Continue.

Reach back out if this does not work and provide the language of the error message.

If you are using the Online version you need to upgrade to Premium to enter a 1099B and investments.  

1099-B import from E*Trade does not work. I have to manually enter acquisition date, sales date etc for the many multiple transactions I have made. This integration is really frustrating as the data import is partial.

If you can't import from Etrade, what error message do you receive?  Here's How to Turn Off Anti-Virus Programs which may be impacting your connectivity.  See if you can import your remaining transactions after this.  

However, if you have multiple transactions and just can't import, it's easier to enter a Summary of each category, rather than the individual transactions.  Here's detailed info on 

How to Enter a Summary in Lieu of Individual Transactions.

@skywalkers