You might try reducing the file size of your 1099-B. For example, Adobe Acrobat can condense a pdf file to a smaller file size from the original. There may be other applications that can reduce file size as well.
Below is a link to a recent TurboTax article that discusses trade limits and file size limits. The import file size is limited to 4 MB.
What if I can't import my 1099-B?
@precious24
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