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So I have a driveway that is made of concrete sections that mates up to the edge of my house which is brick with a cinder block basement wall. The prior owner sealed the gap between the two with cheap sealer which is starting to wear away. So I believe my best option is to take a heat gun, remove all the current sealer and then re-seal the gap with something new.

My question for the community is if it is better to seal the gap with actual cement or with more of a sealer type product? The criteria for "better" is longevity and not letting water in the gap. I do live in a state that gets a decent amount of snow so there is expansion / contraction to worry about. If the choice is a sealer type product, which material choice will hold up the longest? I am not looking for product recommendations, I am looking for material recommendations.

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For raw holding power, sustained flexibility, and general toughness, it's hard to beat modern urethane caulks. Here's a good example (not an endorsement).

Note that urethane in any form (varnish, caulk, spray foam, household glue) is extremely sticky and will instantly ruin clothing and surfaces if it makes contact. It'll also grab skin and hang tight until it wears away.

Also, I don't think a heat gun is the right approach to removing your existing caulk unless it's a thin, soft layer. You'll have a hard time getting enough heat into the bead and surrounding concrete to soften it all the way through. Probably better to just scrape it away.

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