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My H4 visa is going to expire on 31 December and I'm planning to travel to the US on October 31, 60 days prior to my visa's expiry date. Should we expect any issue during immigration?

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Can an H4 visa holder enter the US 60 days prior to the visa expiry?

Yes.

Should we expect any issue during immigration?

No, you should not expect any problems related to the visa's expiration.

A US visa may be used to enter the US up to and including its last day of validity.

Source: https://travel.state.gov/content/visas/en/general/visa-expiration-date.html

What the Visa Expiration Date Means

The visa expiration date is shown on the visa along with the visa issuance date. The time between visa issuance and expiration date is called your visa validity. The visa validity is the length of time you are permitted to travel to a port-of-entry in the United States.

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