Water leaking around chimney - flashing issue maybe?

Had pretty much the exact same issue last spring - minus the bravery of climbing up there myself (heights make me dizzy just thinking about it, kudos to you). I tried the DIY route first, slapped some sealant around the flashing hoping it'd hold... spoiler alert: it didn't. Ended up calling a roofer anyway, who explained flashing needs proper sealing underneath, not just a quick fix on top. Lesson learned the soggy way, lol. Might save yourself some trouble by getting a pro in sooner rather than later.

- Kudos indeed for braving the heights yourself, that's no joke... seriously impressive.
- Interesting point about sealing underneath the flashing - never knew that detail mattered so much.
- Makes me wonder if the previous owners of my house did a proper job or just slapped something on top too. Might explain some mysterious damp spots I've noticed lately.
- Anyway, good on you for sharing your soggy lesson; probably saved a few of us from learning it firsthand, haha.

- Good points all around, but honestly, sealing underneath flashing isn't always the magic bullet. Sometimes the issue is actually higher up - like cracked mortar or even a damaged chimney cap.
- Had a similar issue myself; kept patching and resealing until I finally realized water was sneaking in from above and running down behind everything.
- Might be worth checking out before assuming previous owners cut corners... could save you some hassle climbing up there unnecessarily.

Good advice from everyone so far. I'd say start with a methodical inspection from top to bottom. First, check the chimney cap - make sure it's intact and secured properly. Next, look closely at the mortar joints for cracks or missing sections. If those areas seem fine, move onto the flashing again. If it's rusty and loose as you mentioned earlier, replacing rather than patching might be your best bet. Sealants can buy you time, but they're usually just temporary fixes in my experience.