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I have a question regarding "multiple jobs" since my 2nd job is as an independent contractor and has a W-9.

My previous main job (W-4) did overlap with the side job, but I will not work the independent job once the new job starts.

Should I claim the 2nd job (under contract until Sept) as a second job on the new W-4?

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You should use the W4 estimator to figure out how to fill your new W4.

Generally speaking, W4 is intended to instruct your employer how much to withhold, and you can check the "2nd job" checkbox if both jobs have similar pay and you check it for both of them. If either of these is not true (as is the case here since there's no W4 and withholding for 1099 contract), you'll need to use the estimator to figure out how to fill the form.

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