I've tried both the downloaded version and the cloud version of TurboTax. Software says it is trying to create a secure connection then after a minute or so it fails and says to try again or input manually.
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I can't effectively troubleshoot a technical problem like your in this forum. But I can give you an alternative that is better than manually entering
each transaction. You can enter summary totals for each asset sale
category. It will require you to mail a copy of your Form 1099-B along
with Form 8453 (which TurboTax will generate). To do this in TurboTax
Online,
Click on Search
After entering all your category summaries, Look for "To finish reporting these sales, follow the mailing instructions" and click on the link for these instructions:
This is really not feasible - why can't turbotax upload pdf files of the 1099- from the investments companies and process it? The desktop version has a lot of difficulty connecting to Bank of America, Chase Investments and others to download financial data!
I had the same problem and after weeks of frustration, I found the solution on another thread. The problem is that the TurboTax link has the wrong URL. The link should be to secure05c.chase.com I tried it and 5 minutes later I had the required code and was able to import all of my investment information.
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