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I'm going to reject the premise of your question outright. Windows should be flashed properly and the siding should have a drain plane installed behind it. This isn't a job for caulk.

Some thoughts that may be helpful:

• In modern construction, sill flashing and house wrap provide the actual weatherproofing around and below windows. Your home appears to have neither.
• Vinyl siding provides visual appeal and protection against physical damage. It does not offer much in the way of weatherproofing. Air and wind-driven rain move freely around it.
• That gap is too large for caulk, and the vinyl channel is too flexible as a base for caulk. It would look terrible, and it would likely fail.
• Vinyl siding is meant to move as it expands and contracts due to temperature, and rarely should it be caulked.

I'm afraid I don't have a great solution for you here. Your siding replacement was done very poorly, and there are no shortcuts to a resolution. Your siding contractor failed miserably, in my opinion, by not providing a path to a viable outcome.

I'm going to reject the premise of your question outright. Windows should be flashed properly and the siding should have a drain plane installed behind it. This isn't a job for caulk.

Some thoughts that may be helpful:

• In modern construction, sill flashing and house wrap provide the actual weatherproofing around and below windows. Your home appears to have neither.
• Vinyl siding provides visual appeal and protection against physical damage. It does not offer much in the way of weatherproofing. Air and wind-driven rain move freely around it.
• That gap is too large for caulk, and the vinyl channel is too flexible as a base for caulk. It would look terrible, and it would likely fail.
• Vinyl siding is meant to move as it expands and contracts due to temperature, and rarely should it be caulked.

I'm afraid I don't have a great solution for you here. Your siding replacement was done very poorly, and there are no shortcuts to a resolution. Your siding contractor failed miserably, in my opinion, by not providing a path to a viable outcome.

I'm going to reject the premise of your question outright. Windows should be flashed properly and the siding should have a drain plane installed behind it. This isn't a job for caulk.

Some thoughts that may be helpful:

• In modern construction, sill flashing and house wrap provide the actual weatherproofing around and below windows. You have neither.
• Vinyl siding provides protection against physical damage and visual appeal. It does not offer much in the way of weatherproofing.
• That gap is too large for caulk, and the vinyl channel is too flexible as a base for caulk. It would look terrible, and it would likely fail.
• Vinyl siding is meant to move as it expands and contracts due to temperature, and rarely should it be caulked.

I'm afraid I don't have a great solution for you here. Your siding replacement was done very poorly, and there are no shortcuts to a resolution. Your siding contractor failed miserably, in my opinion, by not providing a viable outcome.

I'm going to reject the premise of your question outright. Windows should be flashed properly and the siding should have a drain plane installed behind it. This isn't a job for caulk.

Some thoughts that may be helpful:

• In modern construction, sill flashing and house wrap provide the actual weatherproofing around and below windows. Your home appears to have neither.
• Vinyl siding provides visual appeal and protection against physical damage. It does not offer much in the way of weatherproofing. Air and wind-driven rain move freely around it.
• That gap is too large for caulk, and the vinyl channel is too flexible as a base for caulk. It would look terrible, and it would likely fail.
• Vinyl siding is meant to move as it expands and contracts due to temperature, and rarely should it be caulked.

I'm afraid I don't have a great solution for you here. Your siding replacement was done very poorly, and there are no shortcuts to a resolution. Your siding contractor failed miserably, in my opinion, by not providing a path to a viable outcome.

I'm going to reject the premise of your question outright. Windows should be flashed properly and the siding should have a drain plane installed behind it. This isn't a job for caulk. Your siding contractor failed miserably, in my opinion.

Some thoughts that may be helpful:

• In modern construction, sill flashing and house wrap provide the actual weatherproofing around and below windows. You have neither.
• Vinyl siding provides protection against physical damage and visual appeal. It does not offer much in the way of weatherproofing.
• That gap is too large for caulk, and the vinyl channel is too flexible as a base for caulk. It would look terrible, and it would likely fail.
• Vinyl siding is meant to move with temperature, and rarely should it be caulked.

I'm afraid I don't have a great solution for you here. Your siding replacement was done very poorly, and there are no shortcuts to a resolution.

I'm going to reject the premise of your question outright. Windows should be flashed properly and the siding should have a drain plane installed behind it. This isn't a job for caulk.

Some thoughts that may be helpful:

• In modern construction, sill flashing and house wrap provide the actual weatherproofing around and below windows. You have neither.
• Vinyl siding provides protection against physical damage and visual appeal. It does not offer much in the way of weatherproofing.
• That gap is too large for caulk, and the vinyl channel is too flexible as a base for caulk. It would look terrible, and it would likely fail.
• Vinyl siding is meant to move as it expands and contracts due to temperature, and rarely should it be caulked.

I'm afraid I don't have a great solution for you here. Your siding replacement was done very poorly, and there are no shortcuts to a resolution. Your siding contractor failed miserably, in my opinion, by not providing a viable outcome.