"maybe worth checking gutters and flashing first?"
Yeah, definitely start there. Had a similar issue years back—spent hours caulking around windows, only to find out it was clogged gutters overflowing down the siding. Cleared them out, problem solved. Weather stripping wouldn't have done a thing in my case.
Had a very similar experience. Spent way too much time sealing around windows, convinced that was the culprit. Turns out water was sneaking in from above—flashing was slightly bent, directing rain right down into the framing. Once we fixed that, no more leaks. Caulk and weather stripping are great for drafts and smaller gaps, but if water's actively getting in, it's usually something bigger like flashing or gutter overflow. Worth checking those first before you spend all afternoon with a caulking gun...speaking from frustrating experience here.
Good points about flashing and gutters, but honestly, sometimes caulk can still do the trick—even with active leaks. Had a window leak last spring, thought it was flashing too, but after climbing up there (not fun btw), everything looked fine. Turned out the old caulk had cracked just enough to let water seep in during heavy rain. Quick scrape and re-caulk around the top edge solved it completely. So yeah, definitely check flashing first, but don't totally rule out caulking either...sometimes it's simpler than you think.
"Quick scrape and re-caulk around the top edge solved it completely."
Agree, caulk can work wonders if it's just minor cracking. But don't overlook weather stripping either—especially if the leak seems more from wind-driven rain or drafts. Quick check: close your window on a dollar bill; if it slides out easy, your weather stripping's shot. Replace it first, then recaulk as needed. Usually solves most window leaks without too much hassle...and saves another trip up the ladder.
Good tip on the dollar bill trick—I learned that one the hard way after a few frustrating weekends of trial and error. Caulk definitely helps, but weather stripping made the biggest difference for me, especially on windows facing the prevailing wind. One thing I noticed though: sometimes leaks aren't even from the window itself. Had a stubborn leak once that turned out to be coming from higher up, near the roofline, and just running down inside the wall. Took forever to figure that out...
Have you checked if your gutters or flashing above the window are in good shape? Sometimes water sneaks in from unexpected places, and sealing around the window alone won't fix it. Might be worth a quick look next time you're up there anyway.
"Had a stubborn leak once that turned out to be coming from higher up, near the roofline, and just running down inside the wall."
Good point about leaks sometimes coming from unexpected places. Had a similar issue myself a while back—spent ages sealing and re-sealing around my window frame, convinced that was the culprit. Turns out the water was sneaking in through a tiny gap in the siding about three feet above the window. It was traveling down behind the siding and coming out right at the window trim, making it look like a window leak.
A couple quick thoughts from my experience:
- Weather stripping definitely helps with drafts, but if you're seeing actual water infiltration, caulk or sealant might be more effective at stopping water penetration directly.
- Don't underestimate siding gaps or cracks in mortar joints (if you have brick). Even tiny openings can channel water surprisingly far.
- Gutters and flashing are good suggestions, but I'd also add checking your siding closely—especially if it's vinyl or wood. Small cracks or loose panels can let water in pretty easily.
Not disagreeing completely about weather stripping—it definitely improved comfort and energy efficiency around my windows—but for actual water intrusion, I've found caulk or silicone sealant usually does a better job. Just my two cents based on what I've seen around my place. Good luck tracking it down... leaks can be tricky!
Had a similar mystery leak myself—spent way too many weekends convinced it was the window itself, replacing weather stripping and caulking around the frame. Turns out it was actually coming from a spot where the flashing met the siding above the window. It was such a tiny gap I never would've guessed, but water was sneaking in, running down behind the siding, and popping out right at the window trim. Sneaky stuff.
Honestly, if you're seeing actual water intrusion, I'd lean more toward caulk or silicone rather than weather stripping. Weather stripping is great for drafts and comfort, but it doesn't really seal out water reliably. Silicone or good exterior-grade caulk is better at actually blocking water infiltration. And don't skimp on quality here—cheap caulk breaks down pretty quickly, especially with exposure to sun and weather.
One thing I'd add to what's been mentioned already: definitely check your flashing carefully. Sometimes builders cut corners there or the flashing gets damaged over time. Gutters also matter more than you'd think—if they're overflowing or clogged, water can easily find its way into weird places like behind siding or trim.
Also, siding itself can be tricky. Had vinyl siding on my house that looked perfect from the outside but had a few loose panels that let water slip right behind them during heavy rain. Took forever to find those spots because everything looked fine at first glance.
Leaks are annoying because they rarely come from where you first think they are. Be patient and persistent—eventually you'll track it down. Good luck...been there myself and know it's a pain.
Had a similar headache myself last spring. Thought it was the window frame too, spent hours caulking and re-caulking, but nope. Ended up being the gutter above—just slightly tilted wrong, so water was overflowing and sneaking behind the siding. Took forever to figure out because it only happened during heavy rain.
Agree with you on weather stripping—it's good for drafts but pretty useless against actual water intrusion. Silicone or quality exterior caulk is definitely the way to go if you're sealing around windows. But honestly, before you start squeezing tubes of caulk everywhere, I'd double-check your gutters and flashing first. It's crazy how far water can travel behind siding before popping out somewhere totally unrelated.
Leaks are sneaky as hell...you think you've nailed it down, then next storm it's back again. Just take your time and check everything methodically. Eventually you'll find it, even if it's in the last place you'd ever expect. Good luck, I feel your pain on this one.
Totally agree—gutters and flashing are often overlooked. I've seen water travel several feet behind siding before showing up near windows. Stick with it, leaks are frustrating but you're clearly on the right track. You'll get there eventually, just keep tracing it step-by-step.
Had a similar issue last spring—thought it was the window itself, but turned out water was sneaking in from a tiny gap in the roof flashing and traveling down behind the siding. Took forever to track down. Caulk helped temporarily, but wasn't a real fix until I sorted the flashing properly. Curious, have you checked if your siding or trim has any hidden cracks or gaps higher up? Water can be sneaky like that...