Is it okay to nail into head flashing into a roof?

New roof with existing new siding. Roofing contractor nailed into head flashing onto new roof. Is this okay or will it leak??

The house is a rear dormered cape. He also nailed into the head flashing at the bottom of the doggie dormers at the front of the house. Please advise if this is correct.

This is correct if he sealed the exposed nail heads.

Another way of doing it,
Is adding a bunch of roofing tar on top of that metal and gluing a “beauty shingle” on top.

Both are correct.

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What should the nail be sealed with?? Silicon or roofing tar??

Either would work.
but i would choose the silicone.

Get some siding caulk close to that colour and they blend right in.

It won’t leak if sealed but it is better to install a screw with a neoprene washer.

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We always set the last show course in a bed of flashing cement then nail with copper or stainless steel roofing nails.