This will be my first time having to file a 1099 related with stocks. Should I wait to file my W-2 until my 1099 arrives (since I can claim losses on my taxable income?), or just go ahead and file my

[fanfare]

don't file an incomplete tax return. That's just nasty.

[JohnW15 · Accepted solution]

You should ideally wait until your Form 1099 arrives, so that you can take advantage of any tax benefits that it might provide.

If you filed without entering any relevant information from that document, and you later want to take advantage of any tax benefits you might have coming, you'd have to file an amended return.

[TomYoung]

Or if you have no "tax benefits", (i.e., losses on trades), you'll still have to amend; it's not optional that 1099s get entered or not.