"I'd also suggest checking the flashing underneath—sometimes it's installed incorrectly or gets damaged over time."
Good point about the flashing. I'm dealing with something similar myself, and honestly, I'm a bit unsure how to tell if it's installed wrong or just damaged from age. Is there a quick way to identify improper flashing installation, or is it more of a remove-and-check-it-out deal? I'd prefer not to pull everything apart unnecessarily, but I also don't want to keep patching with caulk every season...
I've run into this exact issue more times than I'd like to admit. Honestly, you don't always have to rip everything apart right away. First thing I'd do is check visually from outside—look for any obvious gaps, bends, or corrosion around the flashing edges. Sometimes you can spot improper installation if the flashing doesn't overlap correctly or if it's bent upwards instead of angled down and away from the window.
If nothing jumps out visually, try a simple water test. Grab a hose and gently spray around the window frame (start low and work your way up slowly). Have someone inside watching closely to pinpoint exactly where water sneaks in. I once found a tiny gap this way that was invisible otherwise—saved me from tearing out the whole window unnecessarily.
If you do find something suspicious, then yeah, you'll probably need to remove some siding or trim to get a better look. But at least you'll know exactly where to focus your efforts instead of guessing and caulking every year...
I've been down this road too, and honestly, caulk or weather stripping alone rarely solves the issue permanently. A couple years ago, I noticed a small water stain forming under one of my windows after heavy rainstorms. My first instinct was to grab the caulk gun and seal everything in sight. It worked...for about three months. Then the leak was back, same spot, same headache.
"try a simple water test. Grab a hose and gently spray around the window frame (start low and work your way up slowly). Have someone inside watching closely to pinpoint exactly where water sneaks in."
This right here is solid advice. I did exactly that and found out the flashing above my window had been installed backwards—literally funneling water toward the house instead of away from it. No amount of caulk or weather stripping would've fixed that permanently.
Honestly, it's tempting to just patch things up quickly, but if you're seeing repeated leaks, you're probably dealing with something structural or installation-related. Weather stripping is great for drafts and minor moisture issues, but once water finds a path in, it's relentless. I'd skip the quick fixes and spend an afternoon to really figure out what's going on behind the siding. If you catch it early enough, you'll save yourself from bigger headaches down the line (ask me how I know...).
I get what you're saying about structural issues, and you're right—sometimes leaks are a bigger deal than just caulk or weather stripping. But honestly, I've had a different experience. A few years back, I had water sneaking in around my kitchen window every time it rained hard. I was convinced I'd have to rip out siding or redo flashing, but before going down that rabbit hole, I decided to give weather stripping a shot.
Turns out, the old stripping had just dried out and cracked over the years. Replacing it with some quality stuff made a huge difference. It's been almost three years now, and no leaks yet (knock on wood...). So while structural problems definitely happen, sometimes the simpler fix really is enough. I'd say it's worth trying the easy route first before diving into something more involved and expensive.
I hear you, but I'd be careful assuming weather stripping or caulk is always enough. Had a similar issue myself—thought it was minor, ended up being damaged flashing behind the siding. Sometimes the quick fix just masks a bigger problem lurking underneath...
Yeah, that's a good point—sometimes the easy fix just hides the real issue. I had a friend who kept patching up leaks around his windows, thinking it was just old caulk. Turned out his gutters were clogged, causing water to overflow and seep behind the siding. Once he cleaned those out, problem solved. Have you checked your gutters or drainage around the window area yet? Might be worth a quick look before diving deeper into repairs...
Good advice on the gutters—seen that happen more times than I can count. Another thing to consider is the flashing around your window frame. Sometimes builders skimp on proper flashing installation, and over time, water finds its way behind the siding or trim. Have you noticed any signs of moisture damage or discoloration around the interior drywall near that window? Could be worth checking before you commit to caulking or weather stripping fixes...
Flashing is definitely something to check, but honestly... if you're already seeing moisture inside, caulking or weather stripping probably won't solve it. Those are more band-aid fixes. I'd pull back a bit of siding around the window and actually take a look. Had a job last month where the homeowner kept patching with caulk—turned out the flashing was never installed right from day one. Better to check now than deal with mold or rot later.
Yeah, pulling back siding makes sense... but how tricky is that for someone who's never done it before? I'm wondering if moisture inside always means flashing issues, or could condensation from temperature differences also be a factor here?
"I'm wondering if moisture inside always means flashing issues, or could condensation from temperature differences also be a factor here?"
Could definitely be condensation—had something similar happen at my place last winter. I thought for sure it was rain sneaking in, but after pulling back a bit of siding (which honestly wasn't too bad, just took patience and a YouTube vid or two), I realized the insulation around the window was lacking. Added some foam insulation, and problem solved. So yeah, flashing matters, but don't underestimate how much condensation can mess things up too...