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E.g.

If it rains tommorow, and if I don't have an umbrella, I will get wet.

Or

If it rains tommorow and if I don't have an umbrella, I will get wet.

Which of these two is correct from a punctuation perspective? I know that I don't actually need the second if here. But this is obviously a simplified example, so let's say that I wanted to use it. Would I have to put in that additional comma?

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    It depends entirely if you want and if I don't have an umbrella to be parenthetical (extraneous) text or not. If it's essential to what you're trying to convey, then do not use an initial comma; if the sentence would work without it, then add the initial comma. If you replace both commas with parentheses, and the sentence seems fine, then you can leave both commas; if it doesn't seem fine, then remove the first one. I can see an argument both for the second condition being essential and for it just being an aside.
    – Jason Bassford
    Commented Jul 29, 2020 at 13:12
  • I don't see any statutary requirement that would stand up under fair scrutiny either for the inclusion of the first comma or for its omission here. Obscurity doesn't increase either way. As for style, I far prefer 'If it rains tommorow and I don't have an umbrella, I will get wet' to either. The clear winner. But as for the minor places, I'd say that including a second if adds a certain ponderousness (cf McKellen's delivery of 'Tomorrow ... and tomorrow ... and tomorrow ...') that fits well with the comma pause. But a long way behind the winner.
    – Edwin Ashworth
    Commented Jul 29, 2020 at 14:28

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